Cruises & Boat Tours

KEY WEST

Best Cruises & Boat Tours In Key West

Ranked by traveller popularity

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

10 Best Cruises & Boat Tours In Key West

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

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Your Route: Mallory Square, Fort Zachary Taylor, and Sunset Key Moments

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

Most Popular 4.5

A 2-hour Key West sunset sail on a roomy catamaran with an open bar, sangria, hors d’oeuvres, and live local music.

“Honestly worth all the money! Music 10/10, drinks were great & they were able to make mocktails to accommodate our pregnant family member! Food was good & they had plenty of it. They constantly came around to check on us & the views were amazing.”

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

Key West Sunset Cruise: Dinner, Live Music & Drinks Included - The Tropical Buffet Dinner: What You’ll Actually Taste

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Key West Afternoon Snorkel Sail with Unlimited Cocktails! - The ride to the Florida Reef: why it takes time

Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - The Route: From Front Street Check-In to a Two-Hour Evening on the Water

4.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

5.0

Small-group Key West sunset sail with a wine tasting, unlimited beer, and hors d’oeuvres, plus crew stories and a smoother pace for two hours.

“I highly recommend this sunset sail. The wine and apps were delicious and the crew was great. It was such a nice touch to have a wine tasting while enjoying the beautiful sunset. I was really impressed with the selection of wines. I would highly recommend this sail for anyone visiting the area.”

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Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses - Catamaran Echo and the 14-Passenger Advantage

5.Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

5.0

Adults-only Key West sunset champagne cruise on a 14-passenger catamaran: unlimited wine, gourmet cheese, and Moët upgrades.

“It's a fun way to enjoy the sunset. They had many selections besides Champagne and the crew was fabulous. I highly recommend this activity. The boat only seats a small group, and it was delightful.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Sunset Sail with Live Music, Drinks and Appetizers - Unlimited Drinks and Appetizers: What You Actually Get

6.Key West Sunset Sail with Live Music, Drinks and Appetizers

4.5

A 2-hour Key West sunset catamaran with live music, unlimited drinks, and appetizers. Three decks for views. Check in early for seats.

“The boat can seem crowded and not enough seating for everyone but even when full there’s plenty of room to move around. Deck hands were great and made sure everyone had a good time.”

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Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included - Small-Group Sailing at Sea Level: The Feel on Deck

Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - Your Two-Hour Schedule: What Happens From Departure to Sunset

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

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail - The Boat: 65-Foot Schooner and a Manageable Group

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

5.0

Key West full-day sail, kayak, and snorkel with lunch and unlimited drinks, cruising the wildlife refuge on a small schooner.

“The crew are awesome, friendly and knowledgeable. The captain knows his stuff and provides education on how you can assure your safety and have a most enjoyable trip. He is a world class navigator and knows the Keys well.”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Meeting at 205 Elizabeth St and What That Means for Your Timing

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