Key West
Sailing Trips & Tours

Enter your dates to find available activities

Our most recommended Key West Sailing Trips & Tours

Key West: Sunset Cruise with Buffet Dinner and Open Bar

1. 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 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: 3-Hour Coral Reef Snorkeling

3. Key West: 3-Hour Coral Reef Snorkeling

Spend your morning or afternoon snorkeling in warm tropical seas surrounded by colorful fish. Enjoy expert instruction and learn about the reef’s marine wildlife from the professional crew. Your captain will select the exact location based on water and wind conditions, to give you best snorkeling in Key West. Dive into the calm waters, and see how many species of fish and coral you can find. Afterwards, grab a complimentary drink and lay on the sun deck, or cool off in the shade as you sail back to Key West. Feel the breeze in your hair and watch for dolphins playing in the ship’s wake.

Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas

4. 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: All Inclusive Watersports Adventure Tour

5. Key West: All Inclusive Watersports Adventure Tour

Climb aboard a state-of-the-art catamaran and sail to the only living coral reef in North America. Enjoy a delicious breakfast of egg and cheese sandwiches, fresh fruit, granola, and assorted pastries and water, soda and lemonade served throughout the day. Sunbathe and relax on the spacious deck as you cross the Gulf of Mexico for an all-you-can-eat picnic buffet, with sandwiches, fried chicken, veggie and hummus wraps, coleslaw, pasta salad, and cookies. On arrival, snorkel for 1 hour and see angelfish, parrotfish, blue tangs, and other species. Then, cross to the Gulf of Mexico for an all-you-can-eat picnic buffet lunch. Dock at a floating platform and spend the afternoon on jet skis, parasailing, banana boating, and playing aquatic games such as the Action Climbing Tower and Aqua Slide. Cool down with complimentary beer and wine before you sail back to Key West.

Key West: Sunset Snorkel Cruise with Draft Beer & Wine

6. Key West: Sunset Snorkel Cruise with Draft Beer & Wine

Climb aboard a catamaran, and take a 3-hour snorkeling trip out to the coral reef at sunset. Sail across the sparkling waters, moor, and jump into the blue. Snorkel over to the reef and marvel at the abundance of ocean life just below you.   After about 1 hour of snorkeling, climb back into the boat for a leisurely sail back to the port. Sit back and drink some wine or beer while enjoying the magnificent panoramic view of the sun setting over the Gulf of Mexico.

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: Sunset Sailing Trip with Open Bar, Food and Music

8. 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.

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: Eco Safari Tour with Snorkeling

10. Key West: Eco Safari Tour with Snorkeling

Your experience begins as you arrive to the Cow Key Marina on Stock Island. Start by meeting your guide, who teaches you how to operate your own little pistol boat. Your guide then takes off, leading you through the back country of Key West. As you travel you may see ospreys - the only bird of prey to survive entirely on fish. There's also the opportunity to spot manatees feeding on mangroves, sharks swimming beneath you, and pelicans diving for their meals. You soon arrive to Mud Key, a beautiful little sandbar set in the turquoise waters of the Gulf of Mexico. Whilst there, wade in the soothing crystal waters, explore the island, or simply relax. Following your time exploring, begin your journey back to the marina through the winding mangrove maze.

Frequently asked questions about Key West Sailing Trips & Tours

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

The other unmissable things to do in Key West are:

Other Sightseeing Options in Key West

Want to discover all there is to do in Key West? Click here for a full list.

What people are saying about Key West

Overall rating

3.9 / 5

based on 307 reviews

This was a great trip. Was a little disappointed that we had to change locations of the snorkeling because of the weather, not their fault of course but other than that we had a great time. I do recommend eating a little something before since the light breakfast is just a muffin. The crew were great and the mimosas were good. Highly recommend this experience.

Everything went smoothly; the ride was calm, the music, and food we’re nice and so is the staff definitely worth the money!

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!

Very nice sailing tour, super qualified staff and good atmosphere