Schooner Sailing


KEY WEST · FLORIDA KEYS

8 Best Schooner Sailing In Key West

Key West’s best days on the water.

The 8 most popular schooner sailing in Key West. What each trip costs, how long it runs, and who takes you out.

8 Best Schooner Sailing In Key West

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - Where to Meet at Key West Bight (And How Early Matters)
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

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

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

Sail on a replica Key West schooner at sunset with open bar and plated hors d’oeuvres, passing Fort Zachary and classic waterfront views.

Most Popular 5.0

“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 - From William Street to the Historic Seaport: where your evening starts
Cruises & Boat Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Sail Aboard Legendary Schooner Appledore

3.Key West Sunset Sail Aboard Legendary Schooner Appledore

Sail Key West at sunset on a classic wooden schooner with real sail work, small-group calm, and included drinks and hors d’oeuvres.

5.0

“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 - The Two-Hour Sail: How You See Key West Without Getting Sand-Heavy
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

Classic Key West Schooner Sunset Sail with Full Open Bar

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

Classic Key West schooner sunset sail with a full open bar, cocktails, snacks, and a calm small-boat ride past top waterfront landmarks.

5.0

“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 - The 1.5-hour route: what the coast looks like at a sail pace
Cruises & Boat Tours, Key West, Schooner Sailing, Tour Reviews

Key West Day Sail on Schooner America 2.0 with 2 Drinks

Key West Historic Schooner When And If Sunset Cruise - Getting to Perry Marina: slip H16 and the “don’t get lost” tips
Cruises & Boat Tours, Evening Experiences, Historical Tours, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

Key West Historic Schooner When And If Sunset Cruise

6.Key West Historic Schooner When And If Sunset Cruise

Sail Key West at sunset on the historic schooner When and If. Help raise sails, spot dolphins and sea turtles, and enjoy beer/wine.

5.0

“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 - Boarding the Double-Masted Schooner: What You’ll Notice First
Canoes & Kayaks, Cruises & Boat Tours, Kayak Tours, Key West, Reef Snorkeling Tours, Schooner Sailing, Tour Reviews, Tours

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Schooner Appledore Day Sail with Full Bar in Key West - Mallory Square from the Water: The Famous Sunset Scene, Without the Crowds
Cruises & Boat Tours, Drinking Tours, Key West, Schooner Sailing, Tour Reviews

Schooner Appledore Day Sail with Full Bar in Key West

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Every way to get out on the water, and every reason to stay for the sunset.