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Popular Sailing, Catamaran & Gulet Tours Charters in Key West  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sailing, Catamaran & Gulet Tours in Key West, FL- BoatBooker

Key West

Key West, United States

key-west

Discover Key West, Florida, United States from the water, where turquoise channels, sunlit flats, and offshore reefs create a playground for every style of adventure. Key West boating charters unlock calm backcountry mangroves, open Gulf and Atlantic passages, and vibrant reef systems ideal for snorkeling, swimming, and laid‑back cruising.Charter a powerboat to hop between shallow sandbars with postcard‑clear water, or choose a sailing vessel to trace breezy routes past historic waterfronts and colorful island vistas. Wildlife encounters are common here—charters frequently spot sea turtles, rays, tropical fish, and playful dolphins—while clear visibility and gentle conditions make the area welcoming for families and first‑time boaters.From morning eco-excursions to golden-hour voyages, Key West is renowned for spectacular sunsets that paint the horizon, best enjoyed from a comfortable deck with panoramic views. Many itineraries combine multiple highlights in a single outing, such as reef snorkeling followed by a relaxing sandbar stop, or a leisurely sail paired with paddle‑friendly anchorages.Whether you’re planning a private outing, a small‑group adventure, or a full‑day exploration, Key West boating charters offer flexible routes, experienced captains, and year‑round warm waters. With so many distinct marine environments within easy reach, it’s simple to tailor a day on the water that matches your pace—adventurous, relaxed, or somewhere in between.

Experience the vibrant charm of Key West, Florida, with a variety of Key West boat tours that showcase the island's stunning marine life and breathtaking landscapes. Located at the southernmost tip of the United States, Key West offers a unique blend of tropical beauty and rich history, making it an ideal destination for boating enthusiasts.

From sunset sailing trips with open bars and live music to dolphin watching and snorkeling eco-cruises, there's something for everyone in Key West. Explore the crystal-clear waters of the Gulf of Mexico and witness bottlenose dolphins in their natural habitat. Discover the vibrant coral reefs, home to an incredible array of marine life, including sea turtles, stingrays, and colorful fish.

For those who prefer a more leisurely experience, glass bottom boat tours offer a unique opportunity to view the underwater world without getting wet. Enjoy educational commentary while staying cool and comfortable in air-conditioned comfort.

Whether you're looking for adventure, relaxation, or simply a chance to soak up the sun and scenery, Key West boat tours provide an unforgettable experience. With its laid-back atmosphere and stunning natural beauty, Key West is the perfect place to create lasting memories on the water.

Hop aboard one of the nicest boats in town for a sunset cruise in Key West Harbor. On this 2-hour trip, you'll see famous sights like Mallory Square, Sunset Key, and even the Southernmost Point. We have plenty of cooler space, so grab some friends or family, bring a few beverages, and let's set sail for an unforgettable cruise. Departure times vary depending on sunset, typically 2 hours prior.

United States

Good Times Key West 35’ Offshore Express

Good Times Key West LLC is a 2001 Carolina Classic Express Motor yacht based out of Key West. It can take up to six guests. The boat is powered by two 450 HP diesel inboard Cummins engines, offering a maximum cruising speed of 30 knots. The vessel comes e

Embark on the ultimate Key West adventure with our 5-hour Sandbar Safari & Kayak Eco Tour. Cruise aboard our spacious catamaran to a secluded mangrove island, where expert guides lead you through serene mangrove tunnels teeming with wildlife. After kayaking, enjoy a fresh local lunch featuring Cuban sandwiches, chicken tenders, veggie wraps, and more. Then, relax at a pristine sandbar—swim, paddleboard, snorkel, or unwind on a floating lily pad. Unlimited draft beer, wine and mimosas. Perfect for all ages

Sunset Watersports Key West – Sandbar & Kayak

Embark on the ultimate all-inclusive sandbar and kayak adventure in Key West! Escape the tourist crowds as we cruise deep into the pristine waters of the Florida Marine Sanctuary, where dolphins and sea turtles often play alongside our boat. Your journey 

Sail into the famous Key West sunset aboard The Sandie Cat! This lively 2-hour cruise features unlimited tropical drinks, delicious appetizers, and live music from top local entertainers. Enjoy a night of dancing, sipping, and soaking in paradise on Key West’s newest luxury catamaran. From rum runners and margaritas to Hawaiian chicken sliders and more, this all-inclusive experience is the perfect way to celebrate your evening in paradise. Book now and see why it’s one of Key West’s top-rated cruises.

Sunset Watersports Key West – Sunset Sail

Are you ready to experience the Key West sunset like never before? Join us on the ultimate Sunset Sip &amp; Sail adventure aboard The Sandie Cat, our luxurious sailing catamaran! This is more than just a sunset cruise&mdash;it&rsquo;s an experience that&r

A small-group 4.5-hour eco tour featuring a guided kayak adventure through the mangroves and a guided snorkel in the Key West National Wildlife Refuge. Perfect for young families and early risers, with a maximum of 16 guests for a more personal experience.

We provide fresh organic fruit, veggies, hummus, and filtered water. You’re welcome to bring along additional beverages or snacks if you’d like.

Departure times vary

Honest Eco – Sailing Catamaran Blu Q

A perfect platform for eco tours and private charters. With her open layout and unobstructed views of the surrounding sea and sky. This sailing catamaran was built by my first boss in Key West, and many of the captains I admired when I was a mate used to 

Cruise through Key West in style as you soak in the ocean breeze and sweeping coastal views. Drop anchor at a famous local sandbar and dive into waist-deep turquoise water—perfect for swimming, floating, and laid-back lounging under the sun.

45ft Lagoon | Somewhere

The 2018 Lagoon 45 is a modern sailing catamaran that combines French craftsmanship, spacious living areas, and exceptional stability. Designed for comfort and performance, she offers a relaxed yet refined sailing experience ideal for exploring Key West, 

The 8-hour charter includes a light lunch (wraps or sandwiches), a charcuterie board, one welcome alcoholic drink, plus soft drinks and water. On the water, enjoy snorkeling, fishing, exploring mangroves, discovering hidden sandbars, and catching a classic Key West sunset.

Not included: Crew (we provide you one on the day of the charter - 600$), fuel (+\- 100$), and local taxes (7.5%)

Somewhere - Ultimate Catamaran Expedition

Stock Island

Step aboard Somewhere, a stunning 2018 Lagoon 450 Flybridge, and experience the best of the Florida Keys in comfort and style. This 45-foot luxury sailing catamaran is designed for both relaxation and adventure, welcoming up to 12 guests for unforgettable

Snorkel the coral reef, fish from the boat, go lobstering (seasonal), spot dolphins and sea turtles, learn to sail, enjoy dinner at sunset, and more. Perfect for weddings, memorials, corporate events, bachelor/bachelorette parties, eco tours, family adventures, romantic getaways, and more.

Blue Ocean Yacht Charters - Sailing Catamaran

Step aboard the Blue Ocean Yacht Charters &ndash; Fountain Pajot Lucia 40, a sleek sailing catamaran departing from Stock Island, and experience the Florida Keys like never before. Designed for comfort and adventure, this spacious yacht welcomes up to 13 

Blue Ocean Yacht Charters – 50' Sailing Yacht

Step aboard the stunning 2020 Fountain Pajot Saba 50 catamaran, docked in Stock Island, and indulge in the perfect blend of luxury, comfort, and adventure. Designed to host up to 13 guests, this spacious catamaran glides effortlessly on dual 75 HP Volvo d

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through Key West’s backcountry mangrove channels, where you get a chance to escape the hustle and bustle of Downtown and discover the true meaning of bliss. Wade through tropical, clear blue waters, explore the sandbar on a paddleboard, and soak in the picture-perfect setting that this adventure has to offer!

Brightwild Adventures

Experience Key West like never before aboard Brightwild Adventures, a sleek 2020 Power Catamaran that accommodates up to forty guests in comfort and style. Powered by two 300 HP Suzuki outboard engines, she cruises smoothly at up to 16 knots, perfect for 

Brightwild Adventures 2

Brightwild Adventures is a stunning 50ft 2020 Power Catamaran based in Key West, designed for unforgettable experiences on the water. Accommodating up to 40 guests, this vessel is powered by two 300 HP Suzuki outboard engines, cruising smoothly at 16 knot

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