Top Key West Cruises & Sailing

Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.

Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.

Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approach the sandbar, the boat glides over shallow waters, revealing stretches of soft, white sand inviting you to explore. Once you anchor, the fun begins! You can jump off the boat and wade into the warm, shallow waters, where the gentle waves lap at your feet. The atmosphere is relaxed, with laughter and conversation floating through the air. Some folks might set up beach games, while others enjoy swimming or soaking in the sun. Time seems to slow down as you enjoy this little slice of paradise, surrounded by friends or newfound acquaintances. Whether you’re collecting seashells, taking a dip, or simply lounging in the sun, a sandbar trip on a tiki boat is a perfect blend of relaxation and adventure.

Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.

Set sail from Key West on a 60-foot catamaran and enjoy the clear blue waters and Atlantic bottlenose dolphin sightings. Afternoons are when dolphins are the most active so you’re sure to see the adorable creatures jumping and swimming around the boat. You’ll also see some Key West landmarks from the water and enjoy the sea breeze.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.

If you’re looking to snorkel in Key West, but don’t know where to plan your experience, this Key West snorkeling cruise makes things easy. Just prebook this experience, and enjoy a cruise over to a coral reef area—perfect for snorkeling and spotting tropical fish. Plus, all equipment, as well as lessons, breakfast, showers, and a beer or soda is provided for you.

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp (when in season), offering an authentic taste of the region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.

Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vessel for a day of exploration and relaxation. Sailing away from the bustling Key West harbor, feel the gentle breeze on your skin and the warmth of the tropical sun overhead. As the catamaran glides smoothly over the crystal-clear waters, you'll have the opportunity to soak in panoramic views of Key West's picturesque coastline, dotted with palm-fringed beaches and vibrant coral reefs. Keep your eyes peeled for playful dolphins frolicking in the waves or graceful seabirds soaring overhead. After a leisurely sail, stop at a secluded snorkeling spot, where the underwater world awaits exploration. After working up an appetite, indulge in a delicious gourmet breakfast and unlimited mimosas, all while enjoying stunning views and the company of fellow travelers.

After a long day of work or sightseeing, treat yourself to a relaxing 2-hour sunset cruise in Key West. Climb aboard the 47-foot catamaran and set sail along the scenic Floridian coast as the sun sinks into the water. Enjoy unlimited South Florida craft beer, California wine, and hand-crafted cocktails for the duration of the tour.

Take in rare birds–eye views of Key West on a parasailing adventure over Smathers Beach. With a range of departure times offered throughout the day, this tour is a popular, flexible choice for families. Your guide, who ensures that the small group has a personalized experience, takes photos and videos available for purchase after the trip.

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you on an exhilarating, up-close adventure across crystal-clear waters, winding through lush mangroves, stopping at pristine sandbars, and exploring hidden islands that are off the beaten path. This is your chance to experience Key West like never before — in a fun, fast, and eco-friendly CraigCat boat! Perfect for All Levels: Whether you're an experienced boater or a first-time adventurer, the Craigcat is easy to handle and designed for fun and comfort. With a small, nimble design, you’ll have the freedom to explore areas that larger boats or jet skis can’t reach. Up to 4 boats per tour. 2 guests max per boat. If you have 4 people in your group please make two separate bookings to accommodate your party and so forth up to 8 guests.

Discover the vibrant underwater ecosystem of the Florida Keys on a Reef Snorkel Adventure to the renowned Sombrero Key Light Reef. Aboard the luxurious Marathon Mermaid, glide through the crystal-clear waters for an unforgettable snorkeling experience. This 3-hour excursion invites all ages to explore the colorful coral and diverse marine life, guided by a knowledgeable crew dedicated to your safety and enjoyment. After your underwater exploration, relax on the return trip while savoring fresh fruit and refreshing beverages, reminiscing about the aquatic wonders you’ve encountered.

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.

Head out into the open waters on this small-group kayaking and snorkeling ecotour adventure. Follow your captain through scenic mangrove tunnels and over calm waters as you make your way to one of the area's most-stunning snorkeling destinations. Learn about local wildlife before taking a dip and get an underwater look. Gear is provided on this tour that's perfect for all levels.

The Keys are at their most beautiful at sunset. Experience them from the water on this comfortable cruise that includes a glass of sparkling wine to toast the setting sun. Savor winding mangroves and local landmarks like Boot Key Harbor, Sombrero Beach, East Sister Rock Island, and more, culminating in the Seven Mile Bridge.

Snorkel North America’s only living coral reef, then catch an unforgettable Key West sunset, all in one trip. Jump into clear waters with provided gear and spot colorful marine life under the surface. Back on board and after you’re dried off, enjoy rum punch or other beverages on deck as reggae music sets the vibe. A perfect mix of adventure and relaxation, ideal for couples or friends.

Get ready to spend a half-day soaking up the sun and enjoying Key West’s diverse ecology during this fun sandbar and mangrove tour. Discover the backcountry waters and secluded sandbars around the busy island, all while sipping on cold drinks. This guided kayak ecotour takes you into the mangrove isles to spot dazzling marine life before heading to a sandy beach to knock back a few alcoholic or nonalcoholic beverages.