13 Sailing and Snorkeling Trips in Key West Worth Casting Off For

1.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59Our pick

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew supplies masks, fins, instruction, and safety guidance. Expect roughly 45 to 60 minutes in the water, then beer, wine, soft drinks, and cocktails on the ride home. Captain Brett has led some departures.

“The crew is great! They explained how to use the equipment and worked to make the experience a great one!”

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2.Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

★★★★★★★★★★5.0 · 767 reviews · 6 hours 30 minutes (approx.) · from $152Top rated

Join Danger Charters at Opal Key Resort for a 6.5-hour sail aboard a 65-foot schooner. You’ll snorkel in the Florida Keys National Marine Sanctuary, kayak through mangroves, and explore Key West National Wildlife Refuge. Guides such as Daniel, Brian, Joe, and Captain Janet have helped make the trip friendly, informative, and easygoing.

“We had great experience! The crew was amazing:the capital Evan and his crew was very friendly, helpful and made our trip comfortable and so many ways”

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3.Key West Reef Snorkel & Sail Adventure

★★★★★★★★★★4.5 · 540 reviews · 3 hours (approx.) · from $79

Sail from Key West on the 54-foot Floridays, then snorkel a living coral reef with crew guidance and sanitized gear. Captain names vary, with Owen, Chuck, Eric, Alexis, Janet, and others praised for calm, friendly service. Expect roughly 45 minutes in the water, marine life sightings, and included water, soda, wine, and craft beer.

“We had a group of 12 with ages varying from 16 to 63! Everyone enjoyed the sail and snorkel experience! The hosts are helpful, patient, and a ton of fun! Highly recommend this adventure!!”

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4.Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

★★★★★★★★★★4.5 · 370 reviews · 3 hours (approx.) · from $59

Sail from 241 Front Street to a reef selected for the day’s sea conditions. Fury provides instruction, mask, fins, flotation gear, and reef-safe sunscreen. After 30 to 40 minutes in the water, enjoy rum punch, beer, wine, sparkling wine, reggae, and a Key West sunset. You must know how to swim.

“The trip was great, but we expected to see more corals and fish. But it’s not connected to the team.”

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5.Key West Sailing & Snorkeling: A Reef Adventure

★★★★★★★★★★5.0 · 182 reviews · 3 hours (approx.) · from $79

Spend about three hours aboard the 54-foot Floridays, sailing from Key West’s Historic Seaport to a Florida Keys reef. You’ll receive snorkeling gear and instruction, then have time to explore among tropical fish and other sea life. The crew may include captains and mates such as Alex, Janet, Sarah, Eric, or Hunter. Drinks are included, but food is not.

“Clean, well maintained boat. Crew was attentive to details and provided a professional snorkel trip.”

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6.Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco

★★★★★★★★★★5.0 · 177 reviews · 4 hours 30 minutes (approx.) · from $156

Spend 4.5 hours aboard Honest Eco’s 42-foot sailing catamaran, kayaking through shallow mangrove channels, snorkeling at the day’s best calm-water site, and watching for dolphins, turtles, rays, and birds. A small group of up to 16, organic snacks, flotation gear, and instruction make this a relaxed choice for families and first-timers.

“Captain Libby and 1st Mate Brian were great, despite the fact that Brian's a Maine Black Bear ;) They were able to check off all the boxes for this trip starting off with a lucky manatee sighting just as we were preparing to leave the dock. kayaking at Cottrell Key, and as we were transiting to our snorkel spot by Archer Key we happened upon a pod of 8 dolphins. Brian is a wealth of knowledge about the mangroves, the Keys and the wildlife proving he learned something at UMaine. Snorkeling was okay by Archer Key. There are probably better snorkel spots on the Atlantic reef side of Key West.…”

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7.Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

★★★★★★★★★★5.0 · 93 reviews · 5 hours (approx.)

Spend about five hours aboard a traditional double-masted schooner with a small group of up to 20 people. Captain Joe, Sandy, Josh, and crew members such as Michael, Vitale, and Cristina may guide the day, with time for kayaking, snorkeling, sailing under canvas, lunch, and drinks in the Key West backcountry.

“Such a great experience! Captain Sandy and first mate Michael were amazing guides, sailors, hosts and cooks. Highly recommend this 5-hour long sailing, kayaking and snorkeling expedition.”

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8.Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

★★★★★★★★★★4.5 · 80 reviews · 3 hours (approx.) · from $49Best value

Sail from 205 Elizabeth Street at 9 a.m. on a catamaran to a Florida Keys reef, where the crew chooses a snorkel site based on sea conditions. You get gear, a light breakfast from Old Town Bakery, Cuban coffee, mimosas, and a return sail with chances to spot dolphins, turtles, or frigate birds.

“A phenomenal start to a Key West day. Sun, swimming, snorkeling, and plenty to eat and drink. Can't go wrong. If I had more time I would have done it again.”

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9.Sunset Sail + Reef Snorkel & Sandbar

★★★★★★★★★★5.0 · 29 reviews · 4 hours 30 minutes (approx.) · from $143

Join Honest Eco Kayak and Snorkel aboard a 42-foot sailing catamaran for a small-group trip to Sand Key Reef. You’ll learn to use premium snorkel gear, stand on a remote sandbar, snorkel with a guide, and sail back at sunset. Andrew and Kailyn are among the friendly crew members praised for personal care.

“Great trip. The boat wasnt croweded like other tours. Andrew and Cailyn were amazing. If your looking for an intimate tour with a crew that cares about your experience, go with Honest Eco.”

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10.Bimini Charters – Private 3hr Catamaran Charters, Sail & Snorkel

★★★★★★★★★★5.0 · 26 reviews

Spend three private hours aboard a catamaran with captain Nils or another Bimini Charters crew member. Sail Key West, snorkel West Sambo reef, watch for dolphins and turtles, and enjoy the deck or trampolines. Bring your own food and cocktails for a relaxed outing limited to your group of up to six.

“The excursion was fabulous. Our family thoroughly enjoyed the afternoon on the water. Captain Niles and Patrick were knowledgeable of the area and took us snorkeling by the mangroves.”

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11.Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion

★★★★★★★★★★5.0 · 13 reviews · 4h 30m · from $133

Spend 4.5 hours aboard a shallow-draft schooner from Old Town Key West, with guided snorkeling, easy kayaking through mangrove channels, and sunset sailing. Your crew supplies gear, instruction, snacks, soft drinks, water, beer, and wine after the water activities. The group is limited to 20 people.

“On a passé un moment vraiment hors du temps. Ça été notre activité préférée 🤩 je recommande x1000”

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12.Champagne Dolphin Sail and Reef Snorkel

★★★★★★★★★★5.0 · 5 reviews · 3 hours (approx.) · from $108

Set out from Key West with captains Bailey and Micah aboard Catamaran Echo, conditions permitting. You will cruise through local dolphin waters, watch for dolphins and calves, then spend about an hour snorkeling at the coral reef with sanitized gear and simple instruction. Champagne and other adult drinks are served during the roughly three-hour trip.

“we had a truly fantastic time. our captains/guides were Bailey and Micah who facilitated a lovely experience, the views were top notch, and the provisions were plenty. we will be return customers for similar excursions when we return to Key West. thanks for a great day!”

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13.Premium Day Sail, Snorkel &, Kayak with Lunch

★★★★★★★★★★4.3 · 3 reviews · 6h 30m · from $163

Spend a full day on the water with an English-speaking crew from Danger Charters. Sail from Old Town Key West to snorkel sites, kayak mangrove channels in the Florida Keys National Wildlife Refuge, and stop at a beach or sandbar when weather permits. Lunch, snacks, drinks, and all equipment are included.

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