Schooner Cruises

KEY WEST

Best Schooner Cruises In Key West

Ranked by traveller popularity

The 9 most popular schooner cruises in Key West. Here's what they actually deliver, who runs them, and what they cost.

9 Best Schooner Cruises In Key West

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

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

Most Popular 5.0

Key West sunset on America 2.0: beer, wine, champagne, and plated hors d’oeuvres as you pass Fort Zachary and Mallory Square.

“Our captain, Janet was fantastic! She made sure our experience on her ship was perfect including the sunset. Her crew Jade, Milo & Heather were super efficient in not only tending to the ship’s duties but served their guests with a huge smile. Thanks for the great experience!🌞⛵️”

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Key West Sunset Sail Aboard Legendary Schooner Appledore

Key West Sunset Sail Aboard Legendary Schooner Appledore - Helping raise the sails on a globe-touring schooner

3.Key West Sunset Sail Aboard Legendary Schooner Appledore

5.0

Sail Key West at sunset on the classic Schooner Appledore: real sailing, small group vibes, and drinks plus hors d’oeuvres included.

“Our experience aboard the Schooner Appledore was fantastic! Crew members Joe, Mary, and Christina were AMAZING; they were prepared with stories and anecdotes of their time at sea, and it was so fun to learn about their adventures. Drinks were great, apps were yummy, and they were appropriately careful of my spouse’s shellfish allergy. We…”

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Classic Key West Schooner Sunset Sail with Full Open Bar

Classic Key West Schooner Sunset Sail with Full Open Bar - Two Hours on the Water: How the Route Works Without Onshore Stops

4.Classic Key West Schooner Sunset Sail with Full Open Bar

5.0

Small-group Key West schooner sunset sail with full open bar, tasty hors d’oeuvres, and iconic bay views.

“Great outing. Service and experience were at the center of everything Captain Josh and Christina did. Safe loading of passengers, a ‘to the point’ safety overview, almost immediate serving of tasty cocktails/water/etc, and tasty treats (shrimp cocktail, key lime tart, smoked fish with crackers). The boat was nice having padded seating, toilet below deck, and…”

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Key West Day Sail on Schooner America 2.0 with 2 Drinks

Key West Day Sail on Schooner America 2.0 with 2 Drinks - Mallory Square from the water: the coast-town view that clicks

Key West Historic Schooner When And If Sunset Cruise

Key West Historic Schooner When And If Sunset Cruise - The 2-hour sunset timeline: what happens once you’re on deck

6.Key West Historic Schooner When And If Sunset Cruise

5.0

Two-hour Key West sunset sail on a historic schooner. Spot dolphins and turtles, sip beer and wine, help raise sail, small group.

“Historic wooden schooner built by Alden yachts for Gen Patton in 1932. Captain and 2 woman crew were awesome and the sunset was beautiful! 2 hour adventure was perfect with a chance for everyone to participate in the tasks at hand...”

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Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak - Key West National Wildlife Refuge: What You’re Actually Sailing Toward

Schooner Appledore Day Sail with Full Bar in Key West

Schooner Appledore Day Sail with Full Bar in Key West - Mallory Square from the water: sunset energy without the lines

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