Florida Keys
Sailing Trips & Tours

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Our most recommended Florida Keys Sailing Trips & Tours

Islamorada: Snorkeling and Sandbar Catamaran Trip w/ Drinks

1. Islamorada: Snorkeling and Sandbar Catamaran Trip w/ Drinks

Head out of the Florida Keys to relax in Islamorada's peaceful landscape on a catamaran cruise. Stop to snorkel, swim, stand up paddleboard, and relax in the crystal-clear waters. Listen to the relaxing music playing onboard as you sip on cool drinks and feel the salty breeze in your hair. Hop aboard and enjoy the comfort of a spacious power catamaran including shaded seating, a small bathroom, and a large, wide ladder that makes getting in and out of the water nice and easy. Perfectly designed for snorkeling and sandbar cruises, this boat is an ideal choice. Swim in some of the clearest waters in the world. Encounter various fish species, bottlenose dolphins, sea turtles, nurse sharks, and more. Take a dip beneath the crystal clear waters and snorkel at one of the bright reefs before sailing to the world-famous sandbar. Stop to enjoy plenty of time snorkeling, swimming, and paddleboarding while discovering the local and diverse ecosystem. Admire brilliant coral reefs and experience the wildlife of the Keys up close. Choose to paddleboard, float on the surface of the water, or relax with floating mats, music, and a glass of rum punch while taking in the scenery. Relax or play, it's your day.

Key West Double Dip: 2-Stop Reef Snorkeling Trip

2. Key West Double Dip: 2-Stop Reef Snorkeling Trip

The only thing better than snorkeling in Key West is doing it twice! Climb aboard the fast Fury catamaran and head out to Key West’s underwater marvels. During this 3-hour trip you’ll have the opportunity to explore the reef at 2 different locations. The Reef Express is a 57-foot power catamaran built for speed and comfort. It’s the quickest way to get to the reef, so you spend less time traveling and more time snorkeling. Once you reach the reef, you’ll be provided top-of-the-line snorkeling gear including a snorkel, mask, fins and a snorkeling vest. You’ll also get some professional tips and guidance on how to snorkel to better enjoy your experience. After meeting some of the most popular residents – the colorful marine species that inhabit the reef – you'll be transported to another ideal location on the reef for more snorkeling. Double Dip provides approximately 1.5-hours of Key West snorkeling during a 3-hour adventure. If you select the Double Dip Sunset Combo trip, after experiencing the finest Key West snorkeling, the Reef Express will head out to sea to find the perfect place to watch a dramatic sunset. Raise your glass of complimentary Champagne as you toast another fun-filled day in the paradise that is Key West.

Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas

3. Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas

Hop onboard your catamaran for the morning then set sail onto Key West’s glistening turquoise waters towards the third longest reef in the world. During the cruise, soak up epic views of the coastline and snack on a delicious, light breakfast accompanied by mimosas. Upon arrival at the snorkel site, get kitted out with all the necessary gear and listen to a safety briefing. Afterwards, make a splash as you jump into the refreshing, crystal clear water. Follow your instructor as you navigate this impressive coral reef and snorkel in search of colorful marine life. During the experience, enjoy the opportunity to see some of Key West’s 110 species of coral and 500 species of tropical fish. At the end of an epic adventure, relax on deck, grab a beer, and soak up the last of the coastal views as you sail back to port.

Key West: Sunset Party Cruise by Catamaran

4. Key West: Sunset Party Cruise by Catamaran

Climb aboard a party catamaran and sail across the ocean waves on a sunset cruise from Key West. Get ready to dance the night away and cause a commotion on the ocean! Enjoy free hot an cold snacks, including a fresh vegetable platter with hummus and a smoked fish dip with pita chips. Listen to live music as you sip margaritas and wine. Quench your thirst with a cold beer and leave your worries behind as you sail into the sunset. Relax aboard the spacious state-of-the-art catamaran as you cruise the tropical waters. Feel the warm ocean breeze on your face and toast the night with a glass of champagne. Dance to the sounds of your favorite musicians as the sun slowly sets across the sea.

Key West: Glass-Bottom Boat Sunset Cruise and Reef Tour

5. Key West: Glass-Bottom Boat Sunset Cruise and Reef Tour

Climb aboard a glass-bottom boat and cruise the tropical waters of Key West with a warm ocean breeze as your backdrop. Get dramatic underwater vistas before the sun sets, and see a wide variety of fish and other sea creatures. Take advantage of facilities that include restrooms and a snack bar. The catamaran’s twin hull design allows for maximum stability and much less rocking motion than traditional V-hull boats, allowing for maximum viewing with minimum stress to the delicate reef. Marvel at North America’s only living coral reef and one of the most biologically diverse marine ecosystems in the world. See stunning elkhorn coral and impressive brain coral. Listen to explanations about marine life from the experienced captain and crew. Then, toast the end of another perfect day in paradise as you watch the sun set. Relax with complimentary soda and champagne as the sun paints the sky brilliant blues, deep yellows, and lovely shades of orange, pink, and red.

Key West: Sunset Cruise with Buffet Dinner and Open Bar

6. Key West: Sunset Cruise with Buffet Dinner and Open Bar

Climb aboard "The Party Cat" for a wonderful 2-hour cruise around the harbor.   Enjoy a freshly prepared tropical food buffet in an enclosed air-conditioned dining room. Choose from dinner options such as roast pulled pork in mojo sauce, deep fried sweet plantains, black beans and rice, marinated grilled chicken, fried fish, mixed vegetables, mashed potatoes, pasta with mini shrimp and Cuban bread and butter. Sip on your choice of tipple — margaritas, rum runners, champagne, beer, wine or spirits. After dinner, stroll upstairs to the upper deck for live music. Dance the night away or simply listen to the beat as you watch the sun set over the horizon into the Gulf of Mexico. Witness the beautiful display of colors across the night sky.

Key West: Rum and Reggae Afternoon Snorkel and Sunset

7. Key West: Rum and Reggae Afternoon Snorkel and Sunset

Enjoy 2 exciting activities in 1 trip as you snorkel North America’s only living reef system from a spacious catamaran, enjoying the rhythmic sounds of reggae music in tropical waters. Then, watch the sunset over the horizon! Climb aboard the state-of-the-art catamaran from the most luxurious fleet in the Florida Keys. Upon arrival at the reef, get assistance and instructions from the friendly crew before you descend “the stairway to the sea.” Discover the wonders of the aquatic environment and its pristine coral reefs, and snorkel among an abundance of marine life, including tropical species found nowhere else on earth. Upon completion of your snorkeling adventure, enjoy some complimentary rum punch, a signature tropical beverage, beer, wine and champagne. Then, leave your worries behind as you sail off into Key West’s famous sunset. Feel the warm ocean breeze as you watch a magnificent sunset. Toast the end of another perfect day in paradise as you see the sun slowly disappear beyond the horizon.

Key West: 2-Hour Sunset Sail with Live Music

8. Key West: 2-Hour Sunset Sail with Live Music

Set sail on a breathtaking sunset cruise aboard a spacious catamaran. Admire views of the Historic Seaport, pass jugglers and entertainers at the Mallory Square Sunset Celebration, and gaze at Fort Zachary Taylor. Enjoy unlimited drinks and appetizers on board, as well as live musical entertainment. Sail past the landmarks of Key West, as your captain positions the ship to maximize your view of the sunset. Savor a fantastic evening on the water.

Key West: Dolphin Watching & Snorkeling

9. Key West: Dolphin Watching & Snorkeling

Climb aboard the Sunset One dolphin boat, sit back and listen to your tour guide explain where you are and where you are heading. Get ready to watch dolphins frolic in their natural playground.  Marvel as the dolphin swim closer to the boat so you can get a better view. Head out to the small islands within the boundaries of the Key West National Wildlife Refuge. Soak in this beautiful little chain of islands and jump into the gorgeous reef, perfect for snorkeling.  See fish up close and maybe some turtles. Climb back aboard and settle yourself in for the ride back to the dock with an ice cold draft beer. Watch the beautiful panoramic sunset over the crystal clear turquoise waters.

Key West: Sunset Sailing Trip with Open Bar, Food and Music

10. Key West: Sunset Sailing Trip with Open Bar, Food and Music

Join a sailing experience to get you closer to the sunset than ever before. Set sail from the historic sea port of Key West and head straight out to sea for a cruise with unobstructed views of the sunset on the horizon. During the cruise, enjoy an unlimited open bar, with a wide variety of drinks on offer including rum runners, Champagne, margaritas, and draft beer. Taste a selection of finger foods, ranging from Swedish meatballs, veggie treats, cheese and crackers, pita and hummus, and meat and veggie platters. You will be sailing on one of Key West's newest sailing catamarans, the Sandie Cat. This vessel has capacity for up to 149 passengers across 3 decks, so there will always be plenty of room onboard. Grab a drink, head to the upper deck, and dance to live music as you watch the sun go down. The captain and crew will even let you help raise the sails and you can ask to have a picture taken driving the boat.

Frequently asked questions about Florida Keys Sailing Trips & Tours

What are other things to do than Sailing Trips & Tours that are worth visiting in Florida Keys?

The other unmissable things to do in Florida Keys are:

Other Sightseeing Options in Florida Keys

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What people are saying about Florida Keys

We enjoyed the entire experience! We were able to see several dolphins and a couple of youngsters. Staff was super friendly and informative regarding the dolphins. First time snorkeling, the instruction was thorough and I was able to stick out the learning curve and see stingrays, several schools of fish around coral and some various forms of coral. Beautiful day!

Crew was very friendly and knowledgeable! We got to see dolphins and tarpon and the sunset was beautiful!! Would do this again!!

Worth the ticket price. The staffs are helpful and knowledgeable. We went as a family and all of us enjoyed the trip

We had the best crew! Very nice and informative. We loved our time on the boat!

Magnificent tour of the Key West harbor at Sunset!