6 best Sunset Cruises in Key West To Have The Best Time
Looking for the best sunset cruises in Key West but not sure where to start? We’ve got you! Florida, with its stunning landscapes, warm climate, and inviting waters, is one of the most relaxing and romantic destinations in the USA.
Imagine ending a perfect day in this sunny state with one of the most quintessential Floridian experiences – a sunset cruise. It’s an opportunity you wouldn’t want to miss, offering a blend of romance, fun, and breathtaking views as the sun dips below the horizon.
However, with so many options available, choosing the right cruise can feel overwhelming. That’s why we’ve handpicked the best sunset cruises for you.
Whether you’re looking to snorkel among vibrant coral reefs, watch playful dolphins glide through the water, or simply enjoy a dance and a delicious meal against the backdrop of a spectacular sunset, we’ve got something for everyone. Here is our selection of the best Key West sunset cruises.
Our Top 3 Picks:
#1 Pick
#2 Pick
#3 Pick
1. Sunset Sail with Live Music
⭐️ RATING: 4.8/5 Stars | ✅ Book it!
Set off on an unforgettable sunset sailing adventure in Key West. As the sun dips below the horizon, you’ll be treated to a front-row seat on a spacious catamaran, complete with unlimited drinks, appetizers, and the soothing sounds of live music.
This all-inclusive trip isn’t just about the breathtaking views; it’s an immersive experience. From the historic charm of the Seaport to the lively Mallory Square Sunset Celebration and the serene beauty of Fort Zachary Taylor, you’ll sail past iconic landmarks, all while learning about Key West’s unique attractions. It’s the perfect way to cap off a day in the Keys, ensuring your evening is as magical as the setting sun.
We enjoyed every moment. The musical guest was wonderful, the crew was kind and helpful, the food was yummy (small appetizers but there were plenty for seconds!), and the drinks were refreshing. The star of the show was the spectacular view of the sunset from the boat. The boat was not overcrowded so it was very comfortable. – Nicole L., USA (Read more reviews here)
What’s included: sunset views from the water, unlimited drinks, appetizers, live music, views of Historic Seaport, Mallory Square Sunset Celebration, Fort Zachary Taylor.
2. Sunset Cruise With Chances To See dolphins
⭐️ RATING: 4.3/5 Stars | ✅ Book it!
This cruise begins on the Sunset One, a boat dedicated to giving you a front-row seat to nature’s wonders. Listen to the tour guide’s insights as you head out to see dolphins playing in the open water.
Then, dive into the clear waters of Cottrell Key, part of the Key West National Wildlife Refuge, ideal for snorkeling among vibrant marine life. Wrap up this unforgettable trip with a breathtaking sunset cruise back to the dock, beer in hand, after exploring the underwater beauty.
The crew, led by Captain John, is praised for their knowledge and hospitality, making for a fantastic trip, despite the snorkeling spot’s mixed reviews due to jellyfish and less spectacular underwater visibility (Don’t book this one just for the snorkeling).
The tour was well organized so far. The only thing that bothered me was the place where we went snorkeling. You saw one or two fish but everything else was dead from the corals or sponges. I think when you go snorkeling with a guide, you expect a blaze of color underwater and a lot of different species of fish. Unfortunately that wasn’t the case. The snorkeling equipment provided was in good condition, as was the boat. When we went dolphin watching, the guide explained a lot to us about their way of life. That was really good. The staff on board were very friendly. – Tobias, Germany(Read more reviews here)
What’s included: dolphin watching, snorkeling in Key West National Wildlife Refuge, ice cold beer, sunset cruise, 45 minutes snorkeling time, knowledgeable and friendly crew, Captain John, views of dolphins, marine life encounters.
3. Catamaran Sunset Cruise With Live Music
⭐️ RATING: 4.7/5 Stars | ✅ Book it!
This isn’t just any evening; it’s a celebration on the ocean waves where you can dance to live music, feast on delicious appetizers, and enjoy free-flowing drinks. As you sail across the tropical waters, indulge in hot and cold snacks—from fresh veggies with hummus to mojo chicken tenders.
The live music sets the perfect backdrop as you sip on ice-cold margaritas, beer, wine, or champagne, watching the famous Key West sunset painting the sky. The spacious catamaran offers plenty of room to dance, mingle, or just soak in the stunning ocean views and the cooling breeze. It’s a night of carefree joy, where you can let loose and toast to the beauty of the moment as the sun dips below the horizon.
Highly Recommended. The booking went smoothly. The crew was super nice and always provided all guests with drinks. The food was also delicious and plentiful. The sunsets in Florida are a dream anyway. But on the ship with music a great atmosphere! I would do it again and again! – Linda, USA (Read more reviews here)
What’s included: live music, Key West sunset, state-of-the-art catamaran, hot and cold appetizers, free ice-cold margaritas, beer, wine, champagne, tropical waters cruise.
4. 2-Masted Wooden Schooner Cruise With Drinks Included
⭐️ RATING: 5/5 Stars | ✅ Book it!
Jump on board the Appledore II, a stunning 2-masted wooden schooner, for a memorable sunset sail in Key West. As the sun dips, painting the sky with vibrant hues, you’ll have a drink in hand from a wide selection, including champagne, boutique wine, homemade sangria, beer, soft drinks, or a mix from the full cocktail bar.
Not just a passive experience, you’re invited to join in the age-old tradition of raising the sails, adding an interactive twist to your adventure. Glide past Key West’s historic landmarks, including the bustling seaport, Mallory Square’s famous sunset festivities, the impressive navy mole, and the historical Fort Zachary Taylor, dating back to the Civil War era. This journey combines scenic views, historical insights, and the joy of sailing in one unforgettable evening.
Great time. Only 12 passengers so lots of space. – Paul, USA (Read more reviews here)
What’s included: iconic Key West sunset, wide drink selection, participation in sail raising, sights including Fort Zachary Taylor, historic seaport, navy mole, Mallory Square celebration.
5. Sunset Cruise with Buffet Dinner and Open Bar
⭐️ RATING: 4.3/5 Stars | ✅ Book it!
On this cruise, you’ll find an air-conditioned dining room where a tropical food buffet awaits you. The menu’s packed with delicious options like mojo sauce pulled pork, sweet fried plantains, savory black beans and rice, juicy grilled chicken, crispy fried fish, and more, alongside drinks of your choice including margaritas, rum runners, champagne, beer, wine, or various spirits.
After you’ve had your fill, head upstairs to the upper deck. Here, live music sets the perfect backdrop for dancing or just enjoying the sunset as it dips into the Gulf of Mexico, painting the sky with stunning colors. It’s an experience that blends great food, lively entertainment, and breathtaking views all into one.
What a great time. Great food, friendly staff, comfortable setting backed up by a view of the Gulf of Mexico and the sunset. The entertainment was a Jamaican performer from Kingston. He was awesome on vocals, guitar and synthesizer. He knew how to show the group a good time. – Jeffrey, Germany (Read more reviews here)
What’s included: 2-hour harbor cruise, tropical food buffet, enclosed air-conditioned dining, open bar, live music, sunset views over the Gulf of Mexico.
6. Rum and Reggae Afternoon Snorkel and Sunset
⭐️ RATING: 4.3/5 Stars | ✅ Book it!
Dive into a Caribbean adventure with a snorkel tour that ticks two major items off your bucket list in just one trip. Over three hours, you’ll get to explore North America’s only living coral reef system aboard a spacious catamaran, all while grooving to the beats of reggae music.
As if snorkeling in these vibrant tropical waters isn’t thrilling enough, the tour caps off with a spectacular view of the sunset over the horizon. The catamaran, part of the Florida Keys’ most luxurious fleet, offers you a comfortable journey to the reef, where helpful crew members guide you down “the stairway to the sea” for an unforgettable underwater experience. Swim alongside unique marine life that calls this pristine coral reef home.
Afterward, celebrate your exploration with complimentary rum punch, beer, wine, and champagne, raising a glass as the Key West sunset paints the sky. It’s the ultimate way to experience the magic of the Caribbean.
I had a nice time. There were about 20 of us on a large catamaran. We sailed for 45 minutes with explanations before the snorkeling spot. We’re amazed by the fish and I even swam with a turtle. We get back on the boat and enjoy the sunset on the way back with a cocktail and reggae 😍. – Laure, France (Read more reviews here)
What’s included: Caribbean-themed snorkel tour, exploration of living coral reef, reggae music, sunset viewing, spacious state-of-the-art catamaran, complimentary rum punch, beer, wine, champagne, unique marine life encounters.
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We are Mary and Eric, the founders of Be Right Back, a blog dedicated to romance around the globe and at home.
We are Mary and Eric, the founders of Be Right Back, a blog dedicated to romance around the globe and at home. With over 10 years of experience in dating and traveling to romantic places, we share our favorite date ideas and romantic destinations to help couples level up their relationships. Having lived in and traveled through the USA, we also share our favourite things to do in the States.
With 70,000 monthly readers and 16,000 followers on social media, Be Right Back is your go-to resource for romantic trip ideas and couple activities at home and abroad.