1.Key West Champagne Sunset Catamaran Cruise

★★★★★★★★★★4.5 · 586 reviews · 1 hour 30 minutes (approx.) · from $59Our pick

A 69-foot Key West catamaran at sunset with captain-led views, included champagne-style drinks, and a laid-back 1.5-hour sail from the harbor.

“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres. The crew was amazing and on point attending to any needs we had. Highly recommend this cruise.”

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2.Dry Tortugas National Park Day Trip by Catamaran from Key West

★★★★★★★★★★4.5 · 433 reviews · from $220

A full-day catamaran trip from Key West to Dry Tortugas National Park for fort history, beach time, and guided snorkeling.

“Great operation, boat crew and amazing time at the park. You will enjoy it! Just be prepared for the downtime on the ferry there and back.”

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3.Key West Sailing & Snorkeling: A Reef Adventure

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

Sail a 54’ yacht off Key West, snorkel the reef, and enjoy beer, wine, and instruction on a 3-hour small-group trip.

“The boat is big & beautiful especially when there’s only 6 passengers. Crew Sarah & Eric were very pleasant and knowledgeable. The huge disappointment was that we motored out to the reef and back even though it was perfect conditions for sailing. In fact, by the looks of it, that boat has not been under sale for quite some time! I would almost go, as far to say that this is a case of false advertising. The snorkeling was okay. Although the two people who were first-timers had difficulty swimming to the reef while getting accustomed to their snorkel and ended up returning the boat. Sarah continued to offer beverages…”

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4.Shark and Wildlife Viewing Catamaran Tour

★★★★★★★★★★4.8 · 150 reviews · 2 hours · from $99

Two hours on Key West’s Tiger Cat for shark and wildlife viewing in backcountry waters, with shade, drinks, and expert captains.

“Fun trip and my kids loved it. The guides were laid back and very knowledgeable. The whole family had a great time!”

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5.Afternoon Catamaran Sail and Dolphin Watch

★★★★★★★★★★4.5 · 116 reviews · 2h 30m · from $59

Afternoon catamaran in Key West with unlimited drinks and dolphin spotting in the Florida Keys. 150 minutes of sun, sea, and fun.

“We did not see any dolphins, which of course was not the guides fault. I felt like we just did a circle around key west. The boat was not taken too far off the island. Glad we did the activity but have no need to do again”

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6.2 Hour Key West Mini Catamaran Eco Tour

★★★★★★★★★★4.5 · 104 reviews · 2 hours (approx.) · from $264

2-hour Key West mini catamaran eco tour: mangrove channels, sandbar swim, quiet islands, and wildlife spots with small groups and local guides.

“The guide JoJo was very rude and didn’t give proper instructions to us and then yelled at us about 30 minutes into the trip we weren’t doing I right. We were the only members of the tour and he sped off and didn’t see us for much of the trip even when our boat stalled and we struggled to get restarted. He also commented that if he feel in, he would be angry but get us, thank goodness we didn’t fall in. We enjoyed the boats but his nasty attitude damper the trip and I don’t recommend him lead any other people.”

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7.2-Hour Sunset Sailing With Wine In Stock Island

★★★★★★★★★★5.0 · 94 reviews · 2 hours (approx.) · from $125

2-hour sunset schooner sail from Stock Island with wine, beer, and charcuterie included. Small group, attentive crew, big views.

“This was an awesome experience. The food and wine selection was great! Staff was awesome! And the views of the sunset were top notch! Would highly recommend!”

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8.Key West Dolphin Watch and Sunset Sail on Catamaran

★★★★★★★★★★4.5 · 33 reviews · 3 hours (approx.) · from $117

Key West dolphin watch and sunset catamaran sail with snacks, BYOB, and a small group feel for about 3 hours of ocean magic.

“The sunset, the dolphins, being on the water on a beautiful evening. I have as a bit disappointed that we didn’t really sail much because the jib sail was ripped and apparently had been for several weeks. The crew were very chill and worked to make it a pleasurable experience.”

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9.Day Sailing Adventure in the Florida Marine Sanctuary

★★★★★★★★★★5.0 · 30 reviews · 3 hours (approx.) · from $120

3-hour yacht sail in the Florida Keys National Marine Sanctuary from Marathon. See Boot Key Harbor, possible dolphins, and Sombrero Lighthouse.

“Capt. Mike was great! We very much enjoyed our sail! We enjoyed hearing his stories from sailing around the world and the water/ sights were beautiful!”

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

★★★★★★★★★★5.0 · 26 reviews · from $0

Private 3-hour Key West catamaran for up to six: sail the coastline, snorkel West Sambo Reef, spot dolphins and turtles, watch sunset.

“Nills and Jess were friendly and attentive which made for a very relaxing day of sailing and snorkeling.”

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11.Private 90-Minute Harbor Sailing Charter in Key West

★★★★★★★★★★5.0 · 18 reviews · 1 hour 30 minutes (approx.)

A private 90-minute sailing charter in Key West with a captain and mate, views of the coast and wildlife refuge, plus cheese and light refreshments.

“We took the private day sail on december 22, 2025 age range from 15 to 72 a family of 5. Will and Cameron were the best crew we could of possible had. The day was windier than normal so turned out to be excellent day for sailboating. They were very knowledgable and also alot of laughs. This is agreat opportunity for all age groups . Would definately recommend to anyone coming to Key West . This was on our bucket list and would definately do again with this crew if come back to key . Tell the boys if they ever come to Indiana to look us up.”

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12.Catamaran Snorkel with Seafood Boil and Open Bar

★★★★★★★★★★4.4 · 9 reviews · 4 hours · from $89

Key West catamaran snorkel with two stops, premium gear, seafood boil, and an open bar for a sunny 4-hour ocean reset.

“Superbe activité. Équipage très sympathique et agréable. La nourriture était très bonne et boissons à volonté idéal pour se rafraîchir après les plongée magnifiques on a pu faire du snorkeling et voir de très jolis poissons.”

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13.Bimini Charters – Private Luxury Catamaran 3-hr Sunset Sails

★★★★★★★★★★5.0 · 3 reviews · from $137

Private 3-hour Key West sunset sail on a 44-ft catamaran with West Sambo Reef snorkeling, dolphins, and cocktails—no crowds.

“We spent New Year's Eve on a private catamaran trip with Captain Neils and his first mate Simon, and it was everything we could have hoped for. We got started a bit late (totally our fault), but Captain Neils kindly gave us extra time to make sure we still had the full experienRead more”

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14.Catamaran Champagne Sunset Sail

★★★★★★★★★★4.7 · 3 reviews · 1h 30m · from $79

90-minute Key West catamaran sunset sail with unlimited champagne and beer, true sailing, and guided views of famous landmarks.

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