Sailing

KEY WEST

Best Sailing In Key West

Ranked by traveller popularity

The 10 most popular sailing in Key West. Here's what they actually deliver, who runs them, and what they cost.

10 Best Sailing In Key West

Key West Champagne Sunset Catamaran Cruise

Key West Champagne Sunset Catamaran Cruise - The sunset route you’ll feel: Sebago Watersports to Mallory Square to Fort Zachary Taylor

Dry Tortugas National Park Day Trip by Catamaran from Key West

Dry Tortugas National Park Day Trip by Catamaran from Key West - Fort Jefferson: where the history is, and why timing matters

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

Key West: Sunset Sailing Trip with Open Bar, Food and Music - Open bar details that actually matter (and what to plan around)

Key West Sailing & Snorkeling: A Reef Adventure

Key West Sailing & Snorkeling: A Reef Adventure - Where you meet: Hyatt Centric to the water fast

4.Key West Sailing & Snorkeling: A Reef Adventure

5.0

Sail the Florida Keys and snorkel a coral reef on a small-group 54' yacht with drinks and gear included.

“It was a very fun experience especially as first time snorkelers. Enjoyed our time thoroughly. The captain and the co-captain were so helpful and entertaining! we loved the experience!!!”

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2 Hour Key West Mini Catamaran Eco Tour

2 Hour Key West Mini Catamaran Eco Tour - Stop 1: mangrove channels where birds and calm water do the talking

7.2 Hour Key West Mini Catamaran Eco Tour

4.5

Ride a mini catamaran in Key West for 2 hours through mangroves and sandbars, with wildlife chances, small groups, and photo keepsakes.

“As advertised! Had a great time! Cost was very reasonable. Would do it again. Provider did excellent job.”

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2-Hour Sunset Sailing With Wine In Stock Island

2-Hour Sunset Sailing With Wine In Stock Island - Your Two-Hour Timeline: How the Evening Unfolds

8.2-Hour Sunset Sailing With Wine In Stock Island

5.0

2-hour sunset sail from Stock Island with eight wines, five beers, and charcuterie. Small group, schooner crew, stunning views.

“We had a wonderful time on the Wind and Wine Sail! It was great meeting new people while enjoying delicious wine and tasty hors d’oeuvres. One of the highlights was seeing baby dolphins jumping out of the water—such a special surprise. The sunset was absolutely stunning, and the crew was incredibly attentive and knowledgeable throughout…”

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Key West Dolphin Watch and Sunset Sail on Catamaran

Key West Dolphin Watch and Sunset Sail on Catamaran - Dolphin Searching on a Catamaran: What You’re Really Signing Up For

9.Key West Dolphin Watch and Sunset Sail on Catamaran

4.5

3-hour Key West catamaran cruise for dolphins and sunset. BYOB, snacks and water included. Small group max 24.

“It was a wonderful experience. There were only 9 people on the cruise so it was quite cozy. The captain Alexa took us directly to an area where dolphins were plaint and jumping out of the eaters while Heather told us all about them. Heather also cut up fresh fruit and vegetables for us to…”

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Day Sailing Adventure in the Florida Marine Sanctuary

Day Sailing Adventure in the Florida Marine Sanctuary - Boot Key Harbor mooring-field views to start the trip right

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