Florida’s sunny disposition, warm waters, and breathtaking landscapes make it an ideal romantic getaway in the USA. Imagine wrapping up a perfect day with one of the quintessential Floridian experiences – a sunset cruise. This unique blend of romance, fun, and awe-inspiring views as the sun dips below the horizon is an opportunity you won’t want to miss. With numerous options available, selecting the right cruise can feel daunting.
That’s why we’ve curated a selection of the best Key West sunset cruises for you. Whether you’re looking to snorkel among vibrant coral reefs, spot playful dolphins gliding through the water, or simply savor a dance and a delicious meal against the backdrop of a stunning sunset, our handpicked options cater to every preference. Here’s our expertly curated list of the best Key West sunset cruises.
Our Top 3 Picks:
Embark on a unique sailing experience with three exceptional options to choose from. Each 2-hour sail offers a distinct blend of entertainment, adventure, and relaxation.
Option #1: Live Music Sail – Enjoy a 2-hour sail accompanied by high-quality live music in an uncrowded setting. This all-inclusive experience is perfect for those seeking a sophisticated atmosphere.
Option #2: Dolphin-Watching Cruise – Take a sunset cruise and get the chance to spot wild dolphins.
This 45-minute snorkeling adventure also includes beer and a relaxing atmosphere.
Option #3: Catamaran Sunset Cruise with Live Music – Experience the ultimate evening getaway on our catamaran, featuring live music, drinks, and appetizers. A buffet is also included in this memorable experience.
Book your preferred option today!
Sunset Sail with Live Music
Embark on a picturesque sunset sailing adventure in Key West, where the boundaries of relaxation and indulgence blend seamlessly. As the sky transforms into a kaleidoscope of warm hues, you’ll be treated to an unparalleled experience aboard a spacious catamaran, complete with unlimited drinks, savory appetizers, and the enchanting sounds of live music.
This all-encompassing journey isn’t just about taking in the breathtaking views; it’s an immersive exploration of Key West’s iconic landmarks, including the historic Seaport, Mallory Square Sunset Celebration, and Fort Zachary Taylor. As the stars begin to twinkle, you’ll be left with a sense of wonder and awe, making this experience the perfect way to cap off your day in the Keys.
We’ve heard that even the most discerning travelers are impressed by the warm hospitality, delectable cuisine, and refreshing drinks. The pièce de résistance is the spectacular sunset view from the boat, which will leave you breathless. With ample space to unwind and take in the sights, this adventure promises an unforgettable evening under the stars.
Sunset Cruise With Chances To See dolphins
Embark on an unforgettable adventure aboard the Sunset One, a state-of-the-art vessel designed to provide unparalleled access to nature’s splendor. As you set sail, listen attentively to your expert guide as they regale you with insightful commentary on the majestic creatures that inhabit the open waters. The pièce de résistance is a snorkeling excursion in the crystal-clear waters of Cottrell Key, part of the renowned Key West National Wildlife Refuge.
This 45-minute immersion allows for an up-close exploration of the vibrant marine life that calls this unique ecosystem home. As the sun begins to set, unwind with a refreshing ice-cold beer as you take in the breathtaking vistas of the surrounding waters. With Captain John at the helm and his crew’s unparalleled knowledge and hospitality, you’ll be treated to a truly exceptional experience.
While snorkeling may not have been the highlight for everyone due to occasional jellyfish sightings and less-than-stellar underwater visibility, the dolphin-watching excursion proved to be a major draw, with the guide’s engaging commentary providing valuable insight into these intelligent creatures’ fascinating world.
Catamaran Sunset Cruise With Live Music
Experience the ultimate celebration on the ocean waves! This special evening is a chance to let loose and toast to the beauty of the moment as the sun dips below the horizon. Enjoy live music, hot and cold snacks from fresh veggies with hummus to mojo chicken tenders, and indulge in free-flowing drinks including ice-cold margaritas, beer, wine, or champagne. The spacious catamaran offers ample space to dance, mingle, or simply soak up the stunning ocean views and refreshing breeze.
As you sail across the tropical waters, take in the breathtaking views of the famous Key West sunset painting the sky. This night is a true celebration of life, where you can let your hair down and revel in the joy of being surrounded by the beauty of nature. Highly recommended! The booking process was seamless, and the crew went above and beyond to ensure all guests had a fantastic time. The food was delicious and plentiful, and the atmosphere on board was electric.
Don’t miss out on this unforgettable experience!
2-Masted Wooden Schooner Cruise With Drinks Included
Step aboard the majestic Appledore II, a 2-masted wooden schooner, for an enchanting sunset sail in Key West. As the sun sets, painting the sky with vibrant hues, you’ll have access to a diverse selection of drinks, including champagne, boutique wine, homemade sangria, beer, soft drinks, and specialty cocktails from the on-board bar.
This isn’t just a leisurely experience – you’re invited to join in the time-honored tradition of raising the sails, adding an interactive dimension to your adventure. As you glide past Key West’s historic landmarks, including the bustling seaport, Mallory Square’s renowned sunset festivities, the impressive navy mole, and Fort Zachary Taylor, dating back to the Civil War era, you’ll enjoy a unique blend of scenic views, historical insights, and the thrill of sailing.
With only 12 passengers on board, you’re ensured ample space to soak in the atmosphere. This unforgettable evening is perfect for those seeking a memorable experience in Key West.
Sunset Cruise with Buffet Dinner and Open Bar
Experience a delightful blend of flavors and entertainment on this 2-hour harbor cruise. The menu boasts an array of mouthwatering options, including mojo sauce pulled pork, sweet fried plantains, black beans and rice, grilled chicken, crispy fish, and more. Pair your meal with drinks from the open bar, featuring margaritas, rum runners, champagne, beer, wine, or various spirits.
As you dine in comfort beneath the stars, head upstairs to the upper deck where live music sets the tone for an unforgettable evening. Groove to the beat of a talented Jamaican performer from Kingston, who will keep you entertained on vocals, guitar, and synthesizer. With breathtaking views of the Gulf of Mexico as the sun dips below the horizon, this cruise offers an unparalleled combination of great food, lively entertainment, and stunning vistas.
According to satisfied travelers like Jeffrey from Germany, ‘What a great time! Great food, friendly staff, comfortable setting, and a view of the Gulf of Mexico and the sunset. The entertainment was awesome!’ Take in the experience for yourself and make unforgettable memories on this enchanting harbor cruise.
Rum and Reggae Afternoon Snorkel and Sunset
Join a 4.3-star rated snorkel tour in the Caribbean for an unforgettable adventure! Over three hours, explore North America’s only living coral reef system aboard a luxurious catamaran while grooving to reggae beats and enjoying stunning views of the tropical waters. The tour culminates with a breathtaking sunset over the horizon. With helpful crew members guiding you every step of the way, you’ll get up close and personal with unique marine life that calls this pristine coral reef home.
Afterward, celebrate your underwater escapade with complimentary rum punch, beer, wine, and champagne. Whether you’re looking to tick off a bucket list item or simply experience the magic of the Caribbean, this tour is an absolute must! You’ll have a blast snorkeling alongside vibrant tropical fish and even spot a turtle or two (I did!). The catamaran’s spacious decks provide ample room for all 20+ passengers to spread out and take in the views.
We set sail for about 45 minutes before arriving at our snorkeling spot, where knowledgeable guides will have you exploring the reef in no time. As we make our way back to shore, enjoy a cocktail or two while taking in the stunning Key West sunset – it’s the perfect ending to an unforgettable day.
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