4 Key West Boat Tours Worth Booking

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Board Sebago’s spacious catamaran at 205 Elizabeth Street for a two-hour Key West sunset sail. Expect live local music, peel-and-eat shrimp, wine, sangria, beer, cocktails, and soft drinks as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Bring a sweater and arrive 30 minutes early.

“Very well done. Great attitude from the crew which made for a great rise in morale for all the guests.”

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2.Key West Sunset Cruise: Dinner, Live Music & Drinks Included

★★★★★★★★★★4.5 · 1,707 reviews · 2 hours (approx.) · from $92

Board a 65-foot yacht at Key West’s historic seaport for a two-hour sunset sail with crew-served Caribbean buffet, unlimited well drinks, beer, wine, soft drinks, and live music. You’ll pass Mallory Square and the Florida Keys National Marine Sanctuary before returning to the dock.

“Wonderful trip Good food DJ was great Got everyone dancing and even took requests for the kids Great captain”

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3.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

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

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew supplies gear and instruction, then serves beer, wine, cocktails, and soft drinks after snorkeling. Captain Brett has earned special praise for his safety-minded approach.

“Not cruise ship friendly. If you're traveling on a cruise ship, they dropped us off far from our port and made it a difficult boarding. At least let me know, so I can plan accordingly. Because I would not have selected this experience.”

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4.Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125Top rated

Join Danger Charters at 255 Front St for a roughly two-hour sunset sail limited to 26 passengers. Expect wines from around the world, beer, soft drinks, and easy-to-eat hors d'oeuvres, with crew members such as Mary, Connor, Lexi, or Tony sharing stories and keeping the glasses moving.

“Just do it! The crew is wonderful. The wine & appetizers were delicious. It was a chilly and windy sail, but the crew had blankets ready and it was picture perfect. And, a couple got MARRIED during the sail!”

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