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

Sailing, Catamaran & Gulet Tours in Florida Keys- BoatBooker

Florida Keys

Florida Keys, United States

florida-keys

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

Key West

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

Choose from any of the activities we offer during your private boat charter including, but not limited to:

Snorkeling
Sandbar charters
Sunset cruises
Cruising through the mangroves
Wildlife watching
Birdwatching
Lobstering
Sightseeing
Going to lunch by boat
Bar hopping by boat

Not sure? Just request Captain’s Choice and let the captain decide!

Not seeing what you’d like to do on the boat? Simply tell us your request, and we’ll do our best to make it happen!

Islamorada Private Charters

Islamorada

Islamorada Private Charters &ndash; Luxury Catamaran Experience Set sail aboard the stunning Islamorada Private Charters, a custom-built 2019 catamaran offering an unforgettable adventure in the heart of the Florida Keys. This spacious dual-console vessel

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 – 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

Customize your full day boat charter with optional activities including snorkeling, going to the sandbar, crusing theough the mangroves, sightseeing, bar hopping and sunset watching. We also take special requests for other activities!

Islamorada Private Charters – Corinthian 45S

Set sail in style aboard the 2013 Corinthian 45S Catamaran, fully restored in 2025, based in beautiful Islamorada. Perfect for groups of up to 35 guests, this luxurious vessel combines comfort, speed, and versatility for an unforgettable day on the water.

As the sun sets, the tranquil waters of Marathon, Florida, come alive with a mesmerizing display of colors dancing across the sky and reflecting on the gentle waves. Feel the soothing sea breeze against your skin as you recline on the deck of the Marathon Mermaid, sipping champagne and listening to music while immersing yourself in the enchanting atmosphere.

Marathon Mermaid Charters

Marathon

Step aboard Marathon Mermaid Charters, a spacious and stylish 2020 Power Catamaran based in Marathon, designed to comfortably host up to 42 guests, perfect for private parties, celebrations, or unforgettable group outings on the water. Powered by twin 300

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

Experience the magic of the Florida Keys on a 2 Hour – Sunset Tour in Islamorada, where golden skies meet calm, crystal-clear waters. Relax aboard a comfortable boat as you cruise through scenic island channels and watch the sun dip below the horizon in a truly unforgettable setting. Perfect for couples, families, or small groups looking to unwind and take in one of nature’s best shows.

Islamorada Luxe Charters – Islamorada Sandbar

Islamorada Luxe Charters offers an unforgettable luxury boating experience aboard a 2023 Scout 277 Dorado dual console, based in the heart of Islamorada. Designed for comfort and performance, this sleek vessel accommodates up to 6 guests and is powered by

Sailing, Catamaran & Gulet Tours in Florida Keys

Top Sailing, Catamaran & Gulet Tours in Florida Keys