Category Sailing

Key West · SAILING

7 Sailing Trips in Key West That Earn the Fare

7 reviewed

Key West Champagne Sunset Catamaran Cruise

Key West Champagne Sunset Catamaran Cruise - Boarding on a 69-Foot Catamaran: Room, Comfort, and Practical Wins

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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Dry Tortugas National Park Day Trip by Catamaran from Key West

Dry Tortugas National Park Day Trip by Catamaran from Key West - Yankee Freedom III Catamaran Ride: Comfort, Space, and Sea Views

Key West Sailing & Snorkeling: A Reef Adventure

Key West Sailing & Snorkeling: A Reef Adventure - Hyatt Centric Meeting Point and Getting Ready Fast

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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Key West: Shark and Wildlife Viewing Catamaran Tour

Key West: Shark and Wildlife Viewing Catamaran Tour - How the Scented Approach Works for Safer Shark Viewing

Key West: Afternoon Catamaran Sail and Dolphin Watch

Key West: Afternoon Catamaran Sail and Dolphin Watch - Drinks onboard: why unlimited beer, wine, and sangria change the value

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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2 Hour Key West Mini Catamaran Eco Tour

2 Hour Key West Mini Catamaran Eco Tour - Getting Set at 5016 5th Ave: Gear, Age Rules, and the One Thing You Must Check

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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2-Hour Sunset Sailing With Wine In Stock Island

2-Hour Sunset Sailing With Wine In Stock Island - What’s Included Onboard: Wine, Beer, and Sodas

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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