79 Dating Ideas in Boston That Your Partner Will Love

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Are you looking for the best dating ideas in Boston? We’ve got you covered! As a traveling couple, we’ve dated in several countries and cities and have gone on many different dates abroad. From our experience, we have hand picked the most romantic dates in Boston.

Dating can be difficult and finding unique and new dating ideas can be even more of a struggle! 

From unique Boston date ideas to ideas for first dates and creative couples, we share with you the most romantic things to do in Boston in this post.

***Some of the links in this post are affiliate links meaning we earn a small commission at no extra cost to you. This does not change the fact that we only recommend products, stays, activities and attractions we are satisfied with and all opinions expressed here are our own.

First date ideas Boston offers

If you’re dating in Boston, you might be looking for good ideas for first dates. In this section, we share our favorite first date spots Boston offers so you can have a budget-friendly but fun first date!

1.Rooftop drinks in Boston

One of the best casual date spots Boston offers for a first date is The Legal Harborside, where you can sip on refreshing cocktails under a retractable glass ceiling and cozy up by the fireplace. It’s an ideal spot for a first date, especially during sunset when the views are even more mesmerizing. We’ve personally enjoyed many rooftop drink dates together, and it’s always a fantastic idea. Plus, it’s a budget-friendly option for a first date, so you don’t have much to lose. You can also make it a longer or shorter experience depending on how the date is going.

2.Movie at Vintage theatre, one of the romantic date ideas Boston offers

How about catching a movie at one of Boston’s vintage theaters? You can head to Coolidge Corner Theatre or Somerville Theatre for a cinematic experience like no other or even check the Commonwealth Shakespeare Company. These theaters offer a mix of indie and mainstream movies, and the classic red curtain interiors add a touch of nostalgia. It’s a great opportunity to bond over your shared love for film and enjoy an evening filled with captivating storytelling.

3.Go Kayaking together

If you’re up for some outdoor adventure, why not go kayaking on the Charles River? You can rent a double kayak from Paddle Boston and embark on a fun-filled experience together. It’s a great way to enjoy the scenic beauty of the river while paddling side by side. The shared activity will undoubtedly create lasting memories and provide plenty of opportunities for laughter and conversation.

4.Quincy Market

Next on our list is exploring the vibrant Quincy Market, where you’ll find an array of street food stalls offering a diverse culinary experience. Forget about cooking! Here, you can embark on a delightful Boston food tasting adventure, trying different flavors and cuisines together. The lively atmosphere and variety of options make it a perfect spot for a casual first date.

5.Boston Public Market, one of the top food-relating dating ideas in Boston

For a taste of local delights, head to Boston Public Market, one of the top date ideas starting with B in Boston. This culinary destination offers a wide range of foods to explore and enjoy together. You can indulge in delicious bites, from fresh produce to artisanal treats, while savoring the unique flavors of Boston. The flexibility of time allows you to customize your visit and spend as much time as you desire depending on how the date is actually going.

6.New England Aquarium

“It was cool to pet the stingrays” – A 2023 visitor

This is a classic but delightful experience: the New England Aquarium. We’ve had amazing experiences together at other aquariums, like when we were dating in Vancouver, so this is a must-visit for us. Get up close and personal with fascinating marine life and even have the opportunity to touch rays, one of Marie’s favorite memories. It’s a popular local attraction that guarantees a captivating and memorable date.

Check availability and get your tickets here

7.A romantic ferry ride

For fun date ideas Boston offers, a ferry ride is one of them! You can embark on an adventurous ferry ride and explore Boston from a different perspective. It’s an affordable activity that allows you to admire the city’s skyline while enjoying a leisurely boat ride. You can relax, people-watch, and engage in delightful conversations as you soak in the beauty of your surroundings. It’s an ideal choice for a date filled with scenic charm and shared moments.

Cheap date ideas in Boston

As a couple on a budget, we understand that you may also be looking for cheap date ideas Boston offers. In this section, we share the best inexpensive dating ideas and free date ideas Boston offers so you can both enjoy your date with your partner and keep on budget!

8.Boston Symphony Orchestra Afternoon Rehearsal

Like you would go to the Bluebird for a romantic night in Nashville, you can immerse yourself in the world of music by attending an afternoon rehearsal at the Boston Symphony Orchestra. During the mid-day, you’ll have the opportunity to enjoy the enchanting melodies and compositions performed by talented musicians. 

The best part is that tickets for these rehearsals are often available at a more affordable price compared to evening performances, allowing you to experience the magic of the orchestra without straining your budget. Throughout the rehearsal, you can take advantage of the breaks between pieces to chat and share your thoughts on the music, deepening your connection as you appreciate the symphonic artistry together.

9.Picnic at Arnold Arboretum or the Common, one of the cool Boston dating on a budget ideas

For a delightful and budget-friendly date, why not have a picnic at either Arnold Arboretum or the iconic Boston Common? We recommend grabbing a nice blanket and find a cozy spot in the park (That’s what we do!). To make it even more special, consider organizing a color-themed picnic where you bring foods of only one color. This creative idea adds a playful twist to your meal and creates a visually appealing spread. 

What’s great about this dating idea in Boston is that you can use it for a morning date, a hiking date, or even if you’re following the alphabet dating calendar to spice up your routine!

With the beautiful natural surroundings as your backdrop, you can relax, enjoy good food, and engage in meaningful conversations. It’s the perfect setting to chat, get to know each other better, and savor the peaceful atmosphere of nature together.

10.Beacon Hill stroll

You can embark on a delightful stroll through Beacon Hill, a historical neighborhood that exudes charm at every turn. As you wander along the cobblestone streets, surrounded by picturesque red brick buildings and enchanting gas lamps, you’ll feel like you’ve stepped back in time. Take your time to explore the quaint streets and admire the architecture. To satisfy your appetite, make a stop at Tatte Bakery and Cafe, where you can grab a bite to eat and enjoy some delicious treats. The cozy atmosphere and delectable menu options make it the perfect place to relax, indulge, and continue your conversation in a charming setting.

11.Sunset walk at Boston Public Garden

For a simple yet romantic date idea, why not enjoy a sunset walk at the Boston Public Garden? It’s a cost-effective way to soak in the natural beauty and tranquility of the garden. As the sun begins to set, you can savor the captivating colors of the sky while strolling hand in hand. 

To make the experience even sweeter, consider picking up some ice cream along the way. Because who does not like an ice cream date? Treat yourselves to a delicious dessert as you create lasting memories amidst the serene setting of the Boston Public Garden.

12.Petting Zoo outing

If you’re seeking a unique and interactive date idea, explore one of the petting zoos around Boston, such as Drumlin Farm or Holly Hill Farm. At these charming locations, you can delight in the opportunity to pet and feed various animals. Additionally, some farms offer fruit-picking experiences, adding a touch of adventure to your outing. 

Inspired by our recent visit to a pet farm in London, we can assure you that it’s an enjoyable and easy-to-organize date. You can enjoy the outdoor setting, engage in conversation, and let the adorable animals serve as conversation starters.

13.Isabella Stewart Gardner Museum

Make the most of the first Thursday of every month by visiting the Isabella Stewart Gardner Museum, which offers free admission on these special occasions. 

You’ll step into a world of art and beauty as you explore the museum’s stunning Venetian-style courtyard adorned with lush plants, rare artwork, and exquisite furniture. Take your time to appreciate the unique collection and immerse yourselves in the artistic atmosphere. If you need a break or want to extend your date, the museum also features a charming café where you can relax and enjoy a beverage or light snack. It’s a cultural and visually captivating experience that won’t strain your budget.

14.Window shopping at Bow Market

Another cheap dating idea in Boston is going window shopping at Bow Market. This vibrant marketplace is home to a variety of independent boutiques and shops, showcasing a wide range of unique products and artistic creations. Wander through the aisles, exploring the different offerings and enjoying the lively ambiance. 

As you browse, you can even try on matching outfits together, adding a touch of playfulness and connection to your date. Along the way, be sure to grab a snack from one of the food vendors, satisfying your taste buds while you explore the market. It’s an engaging and budget-friendly activity that allows you to bond over shared interests and discover new favorites.

15.Romantic walk on The Greenway

One of the easiest datings ideas in Boston to organize is having a romantic walk along The Greenway, a picturesque park that winds its way through downtown Boston. This idyllic setting provides a serene and scenic backdrop for your date. As you stroll hand in hand, you can take in the beautiful surroundings, people watch, and engage in meaningful conversation. 

The park is also known for its food trucks, offering a wide variety of culinary delights. You can pause along your walk to grab a bite to eat from one of these mobile vendors, adding a delicious element to your outing. Whether you’re enjoying the greenery or sampling tasty treats, The Greenway provides the perfect atmosphere for a leisurely and enjoyable date.

Unique date ideas Boston offers

If you’re looking for out of the box dating ideas in Boston, we’ve got you covered with this list of unusual dating ideas in the city. 

16.Afternoon Sailing Trip, one of the most romantic dating ideas for couples

“This is a nice relaxing sail in the harbor. Really nice crew and other staff, affordable price, affordable simple drinks. Its a very down to earth relaxed atmosphere. We enjoyed ourselves.” – a recent visitor

You can embark on a unique and adventurous date by enjoying an afternoon sailing trip in Boston. Take the wheel and feel the thrill as you help set the sails on a beautiful sailboat. This approximately 2-hour experience allows you to witness the city from a different perspective and offers a refreshing change from your usual dinner and a movie date. With a funny and entertaining captain cracking jokes along the way, laughter is guaranteed as you navigate the sparkling waters and soak in the breathtaking views of Boston’s skyline.

Check availability here

17.Boston duck tour

“Tour guides were great! Highly knowledgeable and you can tell they love what they do. I would defiantly recommend taking the tour.” – Brian M. (Read more reviews here)

For a truly one-of-a-kind date, hop aboard an amphibious vehicle and embark on a Boston Duck Tour. This 80-minute guided tour takes you on a captivating journey through the city’s streets and the Charles River. 

You’ll gain a unique perspective of Boston as you travel seamlessly from land to water. It’s quite funny to look at but it’s even more fun when you’re in the vehicle and you’re just casually going from land to sea!

The tour is led by a knowledgeable and engaging storyteller who will share fascinating facts and anecdotes about the city’s history and landmarks. Buckle up for an exciting and entertaining adventure that will leave you with lasting memories.

Check availability here

18.Uncover the local Mafia, one of the most fun date activities Boston offers

When Eric and I look for fun date ideas near me, we always check if there is a scavenger hunt available as we love those!

With this one, you’ll be able to put your detective skills to the test and embark on a thrilling date to uncover the local Mafia in Boston. Together, you can navigate the city as you work to solve a captivating case filled with puzzles and riddles. This immersive and interactive experience offers a unique opportunity to learn more about Boston’s history and culture while enjoying an engaging and budget-friendly date as it costs less than $10.

You’ll spend approximately 2.5 hours unraveling clues and working together to crack the case. It’s just the two of you against the clock, creating an exhilarating and unforgettable experience.

Check availability here

19.Boston Harbor Cruise

Treat yourselves to a romantic and scenic Boston Harbor Cruise, similarly to cruising across UK’s York with your date. Step aboard a charming vessel and enjoy the company of your date while sipping champagne and taking in the beautiful view of the city and skyline. As you glide along the serene waters, you can immerse yourselves in the enchanting ambiance and create cherished memories together. 

Whether it’s a special occasion or simply a desire to indulge in a memorable experience, a Boston Harbor Cruise offers a delightful blend of relaxation, romance, and breathtaking vistas.

20.Go whale watching

“What an incredible experience! The entire crew was so kind, and very informative! We saw 2 groups of humpbacks and learned so much about them from our guide. You can tell this group is very passionate about what they do. Such a cool experience- highly recommend!” – one of the visitors (Read more reviews here)

For a unique experience in Boston with your partner, embark on a thrilling adventure with a whale-watching excursion in Boston. You’ll join professionals from the Whale Center of New England on a high-speed catamaran equipped with three outside viewing decks. 

You’ll be able to see various whale species, including humpback, finback, and minke whales, as well as playful dolphins. This responsible tour ensures minimal disturbance to the marine environment while providing an unforgettable experience. There are 3 outside viewing decks for the best experience.

The tour lasts about 4 hours surrounded by the wonders of nature, capturing breathtaking moments and creating lasting memories with your date.

Check availability here

21.Glass blowing class, for fun date night places near me

Discover your artistic side and bond with your date during a unique glass-blowing class at Diablo Glass School. This hands-on activity offers a memorable experience where you can learn the art of shaping molten glass into beautiful creations. 

With classes lasting approximately 2 hours, you’ll have the opportunity to explore your creativity, acquire new skills, and create personalized glass pieces together. It’s a wonderful way to engage in a shared learning experience, discover a new passion, and craft lasting mementos of your time together.

22.Puppy yoga, one of the cutest dating ideas in Boston

This is an experience of pure joy and cuteness overload that we can only recommend! We’ve personally enjoyed several puppy yoga classes with adorable cockapoos and Shih Tzus in London, and it’s an absolute delight for a date. You can play “parents” together as you participate in a yoga class surrounded by playful and cuddly puppies. 

The positive energy and happiness radiating from these furry friends create a fun and heartwarming atmosphere, making it a memorable and lighthearted date experience. Check out Water and Rock Studio’s puppy yoga classes for an unforgettable bonding experience.

Find more information here

23.Cat Cafe in Peabody

Indulge in a cozy and charming date at the cat cafe in Peabody, a new addition to the Boston area. Drawing inspiration from our delightful experiences at cat cafes in Dublin, London, Portugal, and Warsaw, this cat cafe allows you to snuggle up with adorable feline companions and even feed them. 

The relaxed and tamed atmosphere provides a perfect setting to connect with your date while enjoying the company of these lovely creatures. Discover the benefits of relaxation and the joy of bonding with cats, making your date a purr-fectly enjoyable experience.

Find more information here

24.Salem Willows Park

A simple but efficient dating idea in Boston is taking a spooky walk on the boardwalk at Salem Willows Park, where you can stroll along the charming boardwalk and immerse yourselves in spooky stories. 

This 7.5-hour day trip from Boston offers a small-group experience, allowing for a more intimate and personalized outing. Explore the historical town of Salem, known for its connection to witchcraft and intriguing folklore. With a guided tour of the Witch Museum and the enchanting ambiance of Salem Willows Park, you can delve into the captivating history and create a date filled with mystery and discovery.

Check availability here

25.Fenway Park Tour

Immerse yourselves in the rich history of America’s favorite pastime with a guided tour of Fenway Park. This interactive experience takes you behind the scenes of the iconic baseball stadium, offering fascinating insights and stories that go beyond the game itself. 

You’ll explore areas not typically accessible to the public, witness the cherished traditions of Fenway Park, and gain a deeper appreciation for the sport. Whether you’re a baseball enthusiast or simply seeking an engaging and informative date, the Fenway Park Tour provides a captivating and memorable experience.

26.Make your own chocolates

I (Marie) am fond of chocolates so this sounds like a dream date idea to me! This unique chocolate-making activity, at LA Burdick Chocolates, allows you and your date to learn the art of crafting delectable chocolates together. Under the guidance of expert chocolatiers, you’ll explore the process of tempering, molding, and decorating chocolates. 

You’ll discover the secrets behind these mouthwatering treats and create your own personalized chocolates to enjoy and share. It’s a delightful and hands-on experience that blends romance, learning, and, of course, the pleasure of savoring delicious chocolates.

27.Castle Island

For a different kind of date, we recommend heading to Castle Island for a relaxing and picturesque date by the water. This scenic location offers stunning views and a serene atmosphere, perfect for unwinding and getting to know each other better.

You can watch planes fly right overhead, adding a unique and captivating element to your conversation. The change of environment and the natural beauty surrounding you serve as excellent conversation starters, allowing you to connect on a deeper level. Soak in the tranquility, enjoy each other’s company, and create memorable moments against the backdrop of Castle Island.

28.Visit the John F. Kennedy Library

If you and your date love history, you’ll love stepping into history and explore the remarkable legacy of President John F. Kennedy at the John F. Kennedy Library. This immersive museum showcases the 1,000 days of Kennedy’s presidency through a combination of HD screens, projections, interactive displays, remastered films, and original artifacts. Delve into the life and impact of one of America’s most beloved presidents as you gain a deeper understanding of his vision and ideals. Engage in thought-provoking discussions, be inspired by Kennedy’s leadership, and appreciate the historical significance of his presidency. It’s a captivating and educational date experience that offers a unique perspective on American history.

29.Afternoon Tea, a classic date idea in Boston 

Why not going for a classic English experience by treating yourselves to afternoon tea at the Boston Public Library? This elegant setting, with its grand marble staircases and classic courtyard, provides the perfect ambiance for a refined and sophisticated date. Delight in an assortment of pastries, sandwiches, and teas as you relax and enjoy each other’s company. 

We recommend booking a table in advance to ensure that you have a reserved spot for this delightful culinary experience. It’s an opportunity to savor delectable treats, engage in meaningful conversation, and create a memorable date steeped in charm and elegance.

Fun date ideas in Boston

In this section, we share fun stuff to do on dates in Boston for fun filled memories.

30.Craft Brewery Tour with a snack, one of the fun dates in Boston

“Rory was our tour guide and he was delightful! Enjoyed trying breweries with new people. Had a great time on our short Boston visit!” – A Visitor (Read more reviews)

You can embark on a delightful craft brewery tour in Boston, starting with the renowned Sam Adams Brewery. Explore the history of beer-making and take a fascinating tour of the facility. But it doesn’t stop there! Boston is home to several other fantastic breweries waiting to be discovered. Enjoy beer tastings and indulge in pretzel snacks as you learn together about the art of brewing. 

The tour typically lasts around 3.5 hours, providing ample time to immerse yourselves in the world of craft beer. Afterward, head over to Ula Cafe, a cozy spot perfect for unwinding and chatting about your favorite brews.

Check availability here

31.Escape Game, one fo our favorite fun Boston dates

Challenge yourselves and put your teamwork to the test with an exciting escape game experience. Boston offers various locations, such as Room Escapers Boston or Escape The Room, where you’ll be locked in a room and must work together to solve puzzles and find clues to escape. 

Drawing from our own enjoyable experiences in Whistler and Dublin, we can assure you that this is a great way to connect as a couple. It feels like you’re part of a thrilling mystery, where every discovery brings you closer to the ultimate goal of breaking free. Prepare for an adrenaline-pumping date filled with problem-solving and adventure.

32.Go to a Red Sox game

Another dating idea in Boston is to immerse yourselves in the excitement of America’s favorite pastime by attending a Red Sox game at Fenway Park. You can cheer for the home team, savor classic ballpark snacks, and soak in the vibrant atmosphere. 

Whether you’re die-hard baseball fans or simply seeking a lively and engaging date, a Red Sox game offers three hours of non-stop entertainment. From the crack of the bat to the roar of the crowd, you’ll be captivated by the energy and camaraderie in the stadium. It’s an experience that embodies the spirit of Boston and creates lasting memories.

Check the next games here

33.Taza Chocolate Factory Tour, one of the fun date places in Boston

Indulge your senses with a chocolate lover’s dream at the Taza Chocolate Factory. Take a guided tour that includes chocolate tastings and the opportunity to witness the traditional stone-grinding process used to make their delectable chocolates. 

This affordable tour, typically priced under $20 per person, offers a unique and educational experience for chocolate enthusiasts. Due to the popularity of the tour, it’s recommended to make an online reservation in advance to secure your spot. So go join a small group of fellow chocolate aficionados and embark on a journey of taste and discovery.

34.For rock climbing and bouldering

Challenge yourselves physically and mentally with a rock climbing or bouldering session at one of Boston’s premier climbing gyms. Central Rock Gym, Boston Bouldering Project, and Rock Spot Gym are just a few options where you can work together to reach new heights and encourage each other along the way. 

You can purchase a day pass, usually around $30 per person, which includes all necessary climbing equipment. Whether you’re experienced climbers or trying it for the first time, rock climbing provides an exhilarating date that fosters trust, communication, and a shared sense of accomplishment.

35.Axe throwing

One of our favorite dating ides in Boston is going for axe-throwing experiences at Urban Axes in Somerville or Revolution Axe Throwing in Everett. This popular activity, priced at around $30 per person for an hour, offers a unique blend of skill, technique, and excitement. 

Eric have gone axe throwing in Vancouver, and we can assure you that it’s super fun! Take turns aiming for the target and see who can score the most points. Alternatively, challenge each other for a friendly competition. Axe throwing is a great way to bond, unleash some energy, and create unforgettable memories together.

36.Go swimming together 

Escape the summer heat and cool off with a refreshing swim in one of the many fresh-water swimming holes near Boston. Crystal Lake in Newton is a prime example, offering a beautiful natural setting for a dip in the water. Pack your swimsuits, towels, and sunscreen, and enjoy a relaxing day by the lake. You can swim, sunbathe, and simply unwind in the serene surroundings. It’s a fantastic way to escape the city and connect with nature while enjoying each other’s company.

37.Adventure to Spectacle Island

Another option is to embark on a short 20-minute ferry ride to Spectacle Island, where adventure and relaxation await you and your date. This island retreat offers a small beach, scenic hiking trails, and breathtaking views of the city skyline. You can explore the island hand in hand, immerse yourselves in the natural beauty, and take in the fresh sea air. Whether you prefer a leisurely stroll or a more challenging hike, Spectacle Island provides the perfect backdrop for quality time together in a tranquil and picturesque setting.

38.Watch the Bruins at Warrior Ice Arena at Boston Landing

If you’re looking for a date that combines sports and entertainment, catch a public hockey game at the Warrior Ice Arena in Boston Landing. You can cheer on the Boston Bruins or other local teams as they showcase their skills on the ice. If you’re feeling adventurous, you can even try your hand at learning to play hockey yourself. 

This date option is perfect for couples who enjoy being active or those who prefer to sit back, relax, and enjoy the fast-paced action of the game. It’s an exciting and dynamic experience that guarantees a fun-filled evening.

39.Chasing waterfalls

Another option for a Boston date is to go on a scenic adventure just a short 30-minute drive from Boston and discover the Cascade in Melrose. We love going on romantic road trips around the world so this one near Boston is no exception!

This hidden gem offers a peaceful retreat in nature, complete with a stunning waterfall cascading down a 16-foot plunge. Take a leisurely hike through the surrounding green space, breathe in the fresh air, and listen to the soothing sound of rushing water. The waterfall serves as a picturesque backdrop for memorable photos and provides a tranquil setting for a romantic stroll. It’s a great way to escape the hustle and bustle of the city and immerse yourselves in the beauty of the natural world.

Creative dating ideas in Boston

In this section, we share cool places to go on dates that are perfect for creative couples. Actually, even if one of you isn’t creative, we still recommend trying them out as you may discover a new hobby or simply a new skill together. 

40.Go to the Theatre, a classic creative date we love

Visiting Boston’s vibrant Theatre District is definitely one of the great date ideas in Boston for creative couples. With iconic venues like the Wang Theatre, Schubert Theatre, and Emerson Colonial Theatre, you’ll have a wide range of shows to choose from. 

Just recently, we had a blast watching The Mousetrap by Agatha Christie. The beautiful buildings themselves add to the charm of the experience. Additionally, consider checking out Harvard’s American Repertory Theatre, known for its innovative and thought-provoking productions. Whether you’re into classic plays, musicals, or cutting-edge performances, the theater offers a unique and enchanting date night that will leave you inspired and entertained.

41.Paint Pottery, one of the creative activities to do on a date in Boston

For a really cool experience, take your partner to a hands-on artistic experience at Clayroom. You can choose a piece of pottery to paint together or opt for individual pieces, from mugs to figurines. 

The best part is that you can bring your masterpieces home as a special memento of your date. Clayroom provides all the necessary supplies, and if you’d like, they can even fire and glaze your pottery for a professional finish. 

It’s a fun and relaxing activity that allows you to express yourselves artistically while spending quality time together. Get ready to unleash your inner artists and create unique keepsakes that will remind you of this special day.

42.Museum of Fine Arts 

Take a trip to the Museum of Fine Arts and immerse yourselves in a world of beauty and creativity. If you’re looking for an affordable option, plan your visit on a Wednesday afternoon when admission is discounted. 

You can explore the vast collection of art spanning various eras and cultures, from classical to contemporary. Art has a way of sparking conversation and igniting new perspectives, making it a perfect backdrop for meaningful moments together. 

Afterward, you can continue the discussion over a drink or a bite to eat, reflecting on your favorite pieces and sharing your interpretations of the artwork. It’s a sophisticated and intellectually stimulating date idea that will leave you feeling inspired.

43.Institute of Contemporary Art

For a dose of modern art and cutting-edge exhibitions, head to the Institute of Contemporary Art (ICA). We recommend taking advantage of free admission on Thursday nights and immerse yourselves in the world of contemporary creativity. 

You can explore the thought-provoking installations and engaging exhibits that push the boundaries of artistic expression hand in hand. Like the Museum of Fine Arts, the ICA provides an excellent starting point for conversations and allows you to delve into your thoughts and interpretations of the artwork. 

After your visit, you can extend the evening by grabbing a drink at a nearby café or bar, discussing your favorite pieces and sharing your unique perspectives.

44.Paint and Sip, one of the fun activity dates in Boston for creatives

Unleash your inner Picasso and enjoy a fun and creative date night at Muse Paintbar. For a fee of around $30 to $50 per person, all the necessary art supplies are included, ensuring you have everything you need to create your masterpiece. You can follow along with a talented instructor as they guide you through the process of painting a specific artwork. 

The relaxed and social atmosphere, combined with a glass of wine or a cocktail, sets the perfect stage for a memorable evening. Whether you’re experienced artists or painting novices, the Paint and Sip experience is all about letting loose, having fun, and embracing your creativity in a lighthearted setting. Get ready to create beautiful artwork together while enjoying each other’s company.

Cute date ideas in Boston

In this section, we share some cute dating ideas in Boston that your partner will definitely love. Most of these can be done as year round dates.

45.Spa day, one of the best date ideas Boston offers

One of our favorite romantic dating ideas is doing a spa date. In Boston, you can treat yourselves to a luxurious spa day at one of the many exquisite spas. Whether you choose Bella Sante, Sway Spa, G2O Spa and Salon, The Spa at Four Seasons Hotel Boston, The Spa at Mandarin Oriental, Boston, Exhale Spa, Rowes Wharf Health Club & Spa, Viyada Thai Spa, or La Moon Thai Spa, you’ll find a haven of relaxation and rejuvenation. 

We recommend going for a couple’s massage to melt away stress and tension, followed by some quality time in the hot tub or pools. The tranquil ambiance and pampering treatments create the perfect setting for getting closer to each other and enhancing your connection. Get ready to unwind, recharge, and luxuriate in a day dedicated to your well-being.

46.Lawn Games, one fo the cute date ideas Boston MA offers

Head over to The Lawn on D in the vibrant Seaport District for an afternoon of fun and laughter. This public space offers swings, food, drinks, and a variety of lawn games. Challenge each other to a game of cornhole, bocce ball, or giant Jenga, and let the friendly competition bring out your playful sides. 

The relaxed and casual atmosphere of The Lawn on D provides a fantastic backdrop for connecting and enjoying each other’s company. Soak up the sun, indulge in tasty treats, and engage in some friendly banter as you create lasting memories together. It’s an easy and lighthearted way to have fun and deepen your bond.

47.Martha’s Vineyard Day trip, one of the best  fall date ideas Massachusetts offers

“Wonderful experience! Jenny our shuttle driver was funny, knowledgeable, and nice! Tom was our guide through Martha’s Vineyard. He was so informative, providing wonderful history and interesting facts about the area. What a beautiful place! Thanks, so much!” (Read more reviews here)

For a top notch cute date idea in Boston, go ahead and book a tour to Martha’s Vineyard, where you’ll experience the charm of this picturesque island. You’ll join a guided tour that includes all transportation, allowing you to sit back, relax, and enjoy the journey. 

You’ll be spending twelves hours total, from Boston, basking in the sun on the beach, exploring the quaint shops, and immersing yourselves in the island’s laid-back atmosphere. Martha’s Vineyard offers a romantic and idyllic setting for a day of relaxation and exploration. Let the ocean breeze and the sound of crashing waves create a serene backdrop as you unwind and enjoy each other’s company. It’s the perfect escape from the hustle and bustle of the city, allowing you to reconnect and create lasting memories together.

Check availability for tours from Boston here

48.Underground Donut tour

“The Boston Underground Donut Tour was absolutely amazing! It was a rainy day downtown, so we got lucky and had a one-on-one with our tour guides. The tour guide and his trainee, Grace, were phenomenal. So knowledgeable, funny, kind and we had the best time chatting & learning with them. The donuts were YUMMY (my fav were the apple cider donuts!) and we got to work them off during the two mile walk. Highly recommended! You won’t be disappointed.”(Read more reviews here)

Take a delicious stroll through Boston’s historic neighborhoods with the Underground Donut Tour. This two-hour tour combines a love for history with a passion for delectable donuts. As you wander through Little Italy and some of the oldest neighborhoods in the city, you’ll sample a variety of mouthwatering donuts from local shops. Food has a way of bringing people together, and this tour is no exception. Discover the city’s rich culinary heritage while indulging your sweet tooth. It’s a unique and tasty experience that allows you to bond over your love for food and explore the hidden gems of Boston’s donut scene.

Check availability here

49.See the blossomed Magnolias 

As simple but super cute Boston date idea is planning a romantic outing along Commonwealth Avenue during early April to witness the blooming magnolias. This enchanting display of nature’s beauty creates a romantic atmosphere that is sure to sweep you off your feet. Take a leisurely stroll hand in hand, surrounded by the delicate fragrance and vibrant colors of the blossoms. 

You can even bring a picnic to enjoy in the park afterwards, immersing yourselves in the serenity of the moment. The blossomed magnolias offer a captivating backdrop for creating cherished memories and enjoying each other’s company in a truly magical setting.

50.Photography walking tour

“The best photographer. I’d recommend him to everyone. Beautiful pictures throughout my weekend. He made me feel comfortable. Moreover this photographer is a very talented person who knows how to capture the moment” (Read more reviews here)

If you like being outside and creative, you’ll like capturing your love and the beauty of Boston with a photography walking tour. Join a one-hour tour that takes you through iconic locations while a professional photographer captures romantic memories of you two. 

You’ll explore the city’s picturesque streets, parks, and landmarks, while the photographer ensures that you have stunning images to cherish. The tour offers a unique way to see the city while creating personalized and intimate photographs that reflect your love and connection. It’s a fantastic opportunity to document your time together and create keepsakes that will bring smiles to your faces for years to come. At the end, you’ll have between 15 and 20 photos of you completely edited to remember this date forever.

Check available dates here 

51.Hot Air Ballon ride

Just an hour away from Boston, you can embark on a breathtaking adventure with a hot air balloon ride. You’ll be able to choose between a sunrise or sunset ride and prepare to be amazed by the incredible views from above together. As you soar through the sky, you’ll witness the stunning landscapes and cityscapes unfolding beneath you. After the one-hour ride, celebrate this unforgettable experience with a champagne toast. 

The romantic ambiance, awe-inspiring vistas, and shared sense of wonder make a hot air balloon ride a top choice for a truly romantic date. It’s an exhilarating and unforgettable adventure that will leave you both in awe.

Find more information here

52.Vegan Ice cream tasting

For a sweet and unique experience, head to FoMu or Emack and Bolio’s Ice Cream for a vegan ice cream tasting. This alternative take on ice cream allows you to try different flavors and discover new tastes together. From dairy-free classics to innovative creations, these vegan ice cream parlors offer a delightful range of options. 

It’s an opportunity to step out of your comfort zones and try something new together. Whether you’re vegan or simply looking for a different twist on a classic treat, the vegan ice cream tasting promises a fun and delicious experience that will satisfy your sweet tooth while keeping your date cute and cruelty-free.

53.Kelleher rose Garden

Take a romantic stroll through the Kelleher Rose Garden located in Back Bay. Adorned with rose-covered archways and vibrant blooms, this enchanting garden offers a serene and idyllic setting for a cute date. While it’s best suited for spring when the roses are in full bloom, any time of the year can be magical in this beautiful oasis. 

As you meander through the garden, hand in hand, you’ll be captivated by the fragrant scents and the beauty that surrounds you. Consider bringing a picnic to enjoy amidst the serene ambiance, adding a touch of romance to your time together. We even recommend bringing along some of your favorite ice cream treats for an extra special touch! We love ice cream!

54.Secret North end food tour

“What can I say? Only good things of course. Gabriel was an absolute engaging guide. The tour started from the moment he greeted us. Each stop along the way was well thought out. There was a nice variety of food to enjoy and sample. Not only did we eat but we learned snippets of key facts about the city and it’s iconic figures. There was never a dull moment for the full 3 hours. Please consider this tour during your visit. It’s relaxing and won’t disappoint. It’s a must do!!!” (Read more reviews here)

Another Boston date idea is to take the Secret North End Food Tour. This three-hour tour takes you through the historic North End neighborhood, known for its rich culinary heritage. Sample a variety of delicious foods, from fresh seafood to Italian specialties, as an engaging guide shares interesting facts about the city and its iconic figures along the way. 

The tour provides a nice variety of foods, ensuring that you’ll savor the authentic flavors of the North End. It’s an opportunity to bond over your shared love for food while exploring the cultural and culinary treasures of Boston. Get ready to indulge your taste buds and discover hidden gems that will leave you wanting more.

Check the dates available here

55.Trip to Gloucester 

For a cute day trip date with your partner, escape to Gloucester for a memorable day trip filled with adventure and natural beauty. Located just a short distance from Boston, Gloucester offers a range of activities, from whale watching to relaxing on the beach. 

For example, you can hop aboard a whale watching tour and marvel at these majestic creatures as they breach the surface of the ocean. Alternatively, you can spend a leisurely day on the beach, soaking up the sun and listening to the soothing sounds of the waves. Gloucester provides a serene and picturesque backdrop for a cute date, allowing you to unwind and create special memories in a coastal paradise.

Boston date night ideas

In this section, we share some of the best date night ideas Boston offers so you can bring your date or partner on a romantic evening and spend a good time together.

56.Sunset Cruise on 1920 yacht, one of our favorite ideas for a date night in Boston

“So much fun. The boat is gorgeously set out with dining tables and lamps, and patio style furniture on the top deck, and the cocktails, drinks and food available was great for such a relatively short harbour cruise. Everything felt really friendly and relaxed. Views of the harbour were fabulous as the sun set.” (Read more reviews here)

For a top notch date night Boston bound, we recommend this romantic evening aboard a highly rated 1920s style yacht with a sunset cruise in Boston. 

This cruise is one of the most popular in the city, offering breathtaking views of the skyline as the sun dips below the horizon. The two-hour journey provides ample time to relax and soak in the beauty of the surroundings. 

You’ll be comfortable onboard with the yacht’s heating and air conditioning, ensuring a pleasant experience no matter the weather. There’s even a bar on the yacht, so you can sip on your favorite drinks while enjoying the stunning scenery. It’s a perfect opportunity to unwind, connect, and create lasting memories against the backdrop of Boston’s sparkling skyline.

Check available dates here

57.Ghost tour for spooky but romantic nights

“Absolutely brilliant, educational yet spooky! We were engaged with the environment for the entirety of the tour, and our guide Zed was exceptional as a character actor, immersing us in the atmosphere. Walking the streets as we learned og their dark history was quite the experience. We’ll be recommending to friends!” (Read more reviews here)

If you’re looking for a thrilling and spine-tingling date night, embark on a ghost tour through the 400-year-old grounds of Boston. This 1.5-hour tour takes you on a journey through history, where you’ll hear chilling ghost stories from the 17th century. 

Join a small group as you explore haunted locations and learn about the city’s dark and mysterious past. The tour is both brilliant and educational, offering a unique way to get closer together as you hold each other tight. It’s an unforgettable experience that will send shivers down your spine and leave you with fascinating tales to share.

Check available dates here

58.Sunset cruise on a tall ship, for water bound date night spots Boston

Step aboard a classic schooner and set sail on a romantic sunset cruise in Boston. This experience allows you to not only enjoy the stunning views but also participate in the sailing adventure. You can lend a hand in raising the sails, making it a memorable and interactive date. 

The duration of the cruise typically ranges from 1.5 to 2 hours, giving you ample time to revel in the magic of the golden hour. Feel the wind in your hair, listen to the gentle lapping of the waves, and witness the sky transform into a masterpiece of colors as the sun sets. It’s a truly romantic and picturesque date night that will leave you both in awe.

Check available dates here

59.Sunset walk at Middlesex Fex

For nature lovers, a sunset walk at Middlesex Fells is a perfect date night idea. This scenic location offers breathtaking views over the Boston skyline, providing a stunning backdrop for a romantic stroll. With numerous trails to choose from, including the Skyline Trail, which spans 8 miles with 1000 ft of elevation gain, you can tailor the hike to your preferences. 

If you prefer a shorter hike, the South Border Parking Lot offers a 3-mile route that still rewards you with beautiful vistas. As you walk hand in hand, surrounded by the beauty of nature, you’ll have the chance to connect and enjoy each other’s company in a serene and tranquil setting.

60.Dinner Cruise

“Such a cool experience! We went on the lunch cruise, the food was very good and was a great selection. We also had a big margarita and got to bring the glass home with us, thought that pretty cool. The views of the Boston Harbor were awesome. The staff were so nice and friendly really made the experience even better. We would definitely come back and do it again.”(Read more reviews here)

We recommend this unforgettable dining experience on a cruise along Boston Harbor. You’ll step aboard a boat that offers music, waterfront views, and a private table for an intimate evening. 

The cruise typically lasts between 2 to 3 hours, allowing you to savor the delicious dinner buffet, which is prepared fresh every day. The cruise takes into account food allergies, ensuring a great selection of dishes for everyone to enjoy. During dinner, you’ll be treated to stunning views of the city skyline and the harbor. 

With rave reviews of a 4.5/5, guests have loved this memorable and romantic date night that combines great food, breathtaking views, and the enchantment of the water.

Check available dates here

61.Murder Mystery dinner

For a fun and unique date night experience, head to Maggiano’s Little Italy for a murder mystery dinner. Enjoy a delectable Italian meal while immersing yourselves in a thrilling murder mystery where you could become a suspect. 

You can engage in conversation with your date as you try to unravel the clues and uncover the truth. It’s an interactive and entertaining evening that adds an element of mystery and excitement to your dining experience. Indulge in delicious food while channeling your inner detective, making memories and laughter together.

62.Comedy Night in Somerville

Get ready for an evening filled with laughter and entertainment at a comedy night in Somerville. These shows are often affordable and feature multiple comedians, offering a variety of humor styles to cater to different tastes. 

Just like when we went to improv nights in Dublin and London, you can expect a great time filled with hilarious performances. Enjoy drinks as you share laughs, creating a light-hearted and joyous atmosphere. It’s a fantastic way to let loose, relax, and enjoy each other’s company while being entertained by some of the best comedians in the area.

63.Star gazing at the observatory

For a romantic and celestial experience, visit the Boston University Coit Observatory for a night of star gazing. The observatory hosts public open nights on Wednesdays, and it’s free to attend. Make sure to reserve your slot in advance to secure your spot. 

You’ll be able to take turns peering through the telescopes and looking at the wonders of the night sky together. It’s a captivating activity that allows you to connect with the universe and each other. Get lost in the beauty of the stars and create magical memories under the vast expanse of the night sky.

64.Charles River Esplanade

Spend a romantic evening on the Charles River Esplanade, where you can enjoy enchanting views of the Boston skyline. As night falls, the city lights twinkle, casting a magical ambiance over the area. Take a leisurely stroll along the riverbank, hand in hand, and revel in the beauty that surrounds you. The tranquil atmosphere provides a perfect setting for intimate conversations and shared moments. 

It’s a romantic spot where you can escape the bustling city and immerse yourselves in the charm of the waterfront.

65.Boston Harbor Walk

The Boston Harbor Walk, a scenic pathway that offers panoramic views of the harbor, is 43 miles long, giving plenty of options for an end of the day romantic walk together. This waterfront promenade is perfect for a leisurely date, especially when combined with delicious ice cream treats. 

There are also plenty of heritage trails that intertwine with the walk, such as the Freedom Trail, the Black Heritage Trail, or the Women’s Heritage Trail. You can immerse yourselves in the rich history and culture of Boston while enjoying the refreshing sea breeze and the captivating sights along the way. It’s an opportunity to appreciate the city’s vibrant waterfront while getting to know each other better.

66.Stroll on Fan Pier Park

Located in the trendy Seaport District, Fan Pier Park offers a delightful setting for a romantic stroll. As you wander through the park, you’ll encounter charming shops and boutiques, adding a touch of vibrancy to your date night. The city lights reflect on the river, creating a magical and romantic ambiance. 

You can take a relaxing walk along the pier, hand in hand, and revel in the twinkling lights and the picturesque views. It’s a serene and charming spot that will make you feel like you’re in a romantic movie scene. You’ll be able to enjoy each other’s company and bask in the enchanting atmosphere of Fan Pier Park.

Indoor and winter date ideas Boston offers

In this section, you’ll find a range of the best date spots Boston offers indoors or that are perfect for winter.

67.The Nutcracker Ballet, one of the best Boston date ideas winter offers

For an elegant date idea in Boston, you can visit the Nutcracker Ballet. This classic ballet performance is a perfect winter date idea, especially during the holiday season. You can both immerse yourselves in the magical world of Clara, the Sugar Plum Fairy, and the Nutcracker Prince as they dance across the stage in a beautiful display of artistry and grace. 

After the show, you can extend the evening by heading out for a cozy and romantic dinner, reminiscing about the breathtaking performance you just witnessed. It’s a fancier date idea that allows you to dress up, experience the beauty of ballet, and create unforgettable memories together.

68.Indoor Race Tracks for fun and good date spots in Boston

This is one of our favorite dating ideas in Boston! A go-karting experience at one of Boston’s indoor race tracks is always a good idea. You can race against each other, feel the adrenaline rush as you zoom around the track, and cheer each other on. It’s a thrilling and action-packed date idea that promises lots of fun and laughter. 

Challenge yourselves to beat your best lap times and create friendly rivalries that will bring you even closer. Whether you’re a seasoned racer or a first-timer, the indoor race tracks in Boston offer a fantastic opportunity to enjoy a high-speed adventure and create unforgettable memories together.

69.Black Light Yoga, one of the fun indoor date ideas Boston offers

Add a twist of excitement to your yoga practice with black light yoga classes. You can find these classes at Sweat and Soul and Back Bay Yoga. Put on your neon and white outfits and get ready to shine in the dark with colors rather than sweat!

The black light illuminates the room, creating a unique and vibrant atmosphere for your yoga session. Move through the poses, surrounded by the glowing colors, and let the energy flow through your bodies. 

It’s a fun and immersive experience that combines fitness, mindfulness, and a touch of adventure. Connect with each other and explore your practice in a whole new light.

70.Drinks in an igloo

For unique and cozy winter dating ideas in Boston, head to The Lookout Rooftop at the Envoy. Here, you can enjoy drinks and get to know each other in heated igloos. This unique setting provides an intimate and picturesque atmosphere to share conversation and laughter. 

You can snuggle up together, sip on your favorite cocktails, and marvel at the stunning views of the city. It’s a perfect spot to escape the chilly weather while creating a memorable and romantic experience. Let the warmth of the igloo and the company of each other make this date night truly special.

71.Ice skating on the Frog Pond, one of the best date places in Boston

For romantic dating ideas in Boston, you can take your date to experience the romance and joy of ice skating hand in hand on the picturesque Frog Pond. This outdoor ice rink, located in the heart of Boston, is a perfect destination for a winter date. You can glide across the ice, surrounded by the twinkling holiday lights, and embrace the magic of the season. 

The rink is open every day except Mondays, and it costs about $6 per person with skate rentals available for $12. You can hold each other close as you twirl and glide under the winter sky, creating beautiful memories that will last a lifetime. It’s a classic and romantic activity that captures the essence of winter in Boston.

72.Other ice skating locations

If you’re looking for more ice skating options, consider visiting the rink at 401 Park in Fenway or Skate @ Canal District Kendall in Cambridge. These alternative locations provide additional opportunities to enjoy the thrill of ice skating in different parts of the city. You can also explore Keely Outdoor in Jamaica Plain, which offers a charming and less crowded setting for a delightful skating experience. We love ice skating as it’s always so fun! Plus, Eric used to do ice hockey so it’s quite fun to skate with hime!

So lace up your skates, hold hands, and explore these wonderful ice rinks together, creating winter memories that will warm your hearts.

73.Skiing together near Boston

For dating ideas just outside Boston, head to Blue Hills, where you can hit the slopes and go skiing. Located only 20 minutes away from the city, Blue Hills offers a convenient escape to enjoy the thrill of skiing together. Slide down the slopes, feel the rush of the wind against your faces, and embrace the winter scenery surrounding you. 

If skiing is not your thing, consider an alternative like the Skyline Trail. This 15-mile trail with a 3,500-foot elevation gain offers a challenging and rewarding hiking experience, allowing you to immerse yourselves in nature and enjoy breathtaking views of the Boston skyline. It’s a perfect way to embrace the winter season and engage in an active and adventurous date together.

Romantic hotels in Boston

In this section, we share the best hotel places for dates in Boston so you can have the most romantic Boston dates through the night!

74.The Liberty for one of the best dates in Boston

For a romantic night in Boston, you can experience a unique blend of history and modern luxury at The Liberty hotel. This former jail has been transformed into a contemporary masterpiece, combining elegant design with a touch of intrigue. Located in the heart of Boston, you’ll find yourself surrounded by the city’s vibrant energy and rich culture. 

You’ll be able to step into a world where old meets new, where the past echoes through the hallways while the present embraces you with comfort and style. The Liberty offers a truly memorable stay, immersing you in an atmosphere that is both captivating and romantic.

Check availability here

75.Fairmont Copley Plaza

Step into a world of timeless elegance at the Fairmont Copley Plaza. This historic hotel, built in 1912, exudes a Gatsby-esque charm that will transport you back in time. Located in the Back Bay neighborhood, you’ll find yourself immersed in the beauty of Boston’s architectural wonders and cultural attractions. Indulge in the opulence of the hotel’s immersive style, with luxurious accommodations and exceptional service. 

From the moment you enter the grand lobby, you’ll be greeted with a sense of grandeur that sets the stage for a truly romantic stay in the heart of the city.

Check availability here

76.The Godfrey

Discover a hidden gem with a stay at The Godfrey hotel. This boutique hotel, built in 1908, boasts a stunning Gothic Revival facade that will capture your attention from the moment you arrive. Located near Boston Common, it offers the perfect base for exploring the city’s vibrant neighborhoods and iconic landmarks. 

After a day of adventures, retreat to the comfort of your room and indulge in the hotel’s Japanese-Peruvian Fusion restaurant, offering a unique and delectable dining experience. The Godfrey combines history, style, and a prime location to create a memorable and romantic getaway.

Check availability here

77.The Lenox

A luxurious escape at The Lenox, a boutique hotel nestled in Boston’s Back Bay neighborhood, is always a great date idea. This elegant hotel partners with G2O Spa to provide you with a pampering experience that will leave you feeling refreshed and rejuvenated. Immerse yourselves in the sophisticated ambiance of the hotel, featuring refined decor and impeccable attention to detail. 

The Lenox also partners with local New England providers, ensuring that you have an authentic and memorable experience that reflects the charm and character of the region. From the moment you step into The Lenox, you’ll be enveloped in a world of luxury and warmth.

Check availability here

78.Boston Harbor Hotel

This five-star Boston Harbor Hotel overlooks the picturesque Boston Harbor, and offers a prime location and breathtaking views that will sweep you off your feet. Immerse yourselves in the lap of luxury with impeccable service, exquisite accommodations, and world-class amenities. 

From the moment you arrive, you’ll be treated like royalty, with every detail attended to. Whether you’re enjoying a romantic dinner at one of the hotel’s acclaimed restaurants or strolling along the harbor promenade hand in hand, the Boston Harbor Hotel provides an unforgettable setting for a truly romantic escape.

Check availability here

79.Battery Wharf Hotel

Unwind and rejuvenate at the Battery Wharf Hotel, where relaxation and luxury await. This waterfront hotel offers an on-site spa, allowing you to indulge in blissful treatments and unwind from the stresses of everyday life. Immerse yourselves in the tranquil ambiance as you enjoy stunning views over Boston Harbor. From the moment you step into the hotel, you’ll be enveloped in an atmosphere of serenity and sophistication, creating the perfect backdrop for a romantic getaway.

Check availability here

Best dating apps in Boston

• Bumble: A dating app where women make the first move, empowering users to take control of their dating experience.
• Tinder: A popular dating app that allows users to swipe right if interested or left if not, making it easy to match and connect with potential partners.
• Her: Designed for LGBTQ+ women, Her is a social and dating app that fosters a supportive and inclusive community for queer individuals to meet and connect.
• Coffee Meets Bagel: This app focuses on quality over quantity, providing users with curated matches called “bagels” each day, encouraging meaningful connections.
• Happn: A unique dating app that matches users based on their real-life proximity, allowing you to connect with people you’ve crossed paths with, adding an element of serendipity to your dating experience.

Dating ideas in Boston FAQs

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