Key West

Florida

Experience a Key West bucket list experience on one of our historic Schooners. Choose from our award winning Key West Sunset Sail, Key West Windjammer Day Sail, Key West Eco-Tour or start your vacation with our Key West Bloody Mary Sail.

Schooner Appledore - Key West

Schooner Appledore

Catch the wind on an historic, dual-masted sailing vessel for a pleasure cruise through beautiful Key West, Florida with a Windjammer Schooner Day Sail. Journey the calm, tropical waters to view landmark sites like Fort Zachary Taylor, the Navy Mole, and opulent Sunset Key. Sample a wide variety of premium complimentary drinks like homemade sangria, draft beer, premium wine, and more. Climb aboard an authentic sailing schooner for this luxurious day sail and cast your cares into the warm breeze. Book your spot today on this Windjammer Schooner Day Sail.

Windjammer Schooner Day Sail

Catch the wind on an historic, dual-masted sailing vessel for a pleasure cruise through beautiful Key West, Florida with...

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West, Florida. This sailing vessel is fit for royalty, with its wide decks and ample seating and includes an open bar. Journey in comfort to landmark sites like the Navy Mole, Fort Zachary Taylor, Sunset Key, and more as the sails are hoisted and the tropical breeze whisks your cares away. Witness the beauty of a Key West Sunset and behold the grandeur of the star-filled Southern sky on this cruise. Book today!

Windjammer Champagne Sunset Sail

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West,...

With sunset sails being very prominent in Key West, we were pleasantly surprised to find this a very personal experience.  The live aboard crew members were very approachable, took time to talk to anyone who asked questions and shared their love of the water.  The Hors d'oeuvres were very classy and the  alcoholic beverages were well done.  This sail exceeded our expectations and we would highly recommend the Appledore II Schooner to anyone considering doing a Key West Sunset Sail.

Authentic Schooner Sunset Sail

Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline water to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!

Schooner Champagne Sunset Sail

Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a...

From the point of booking through to the end of the trip everything that was in was within the control of the crew was very nice  
Jamie, Bradley & Capt Mario were excellent.

Excellent

everything was exceptional and all the crew were very accommodating

sunset cruise

If you're looking for one of the best sunset cruise experiences in Key West, this is it. My wife and I booked this cruise without knowing much about it, but we knew that we wanted to be on a boat that had fewer people than the big boats, and a more intimate experience. That's exactly what we got. The crew consisting of Russ the Captain, Isaac the First Mate, and Laura (her second day on the job) were the absolute best. They were fun, funny, willing to answer our silly questions, and went above and beyond to serve us first class snacks and excellent, top shelf drinks. They played music that added to the ambience. We made great friends on the boat and enjoyed the sail. The evening was perfect, the sea was calm, the sunset was spectacular, and there was a full moon that rose immediately after the sunset. This cruise was worth every penny we paid for it. We would do it again in a heartbeat. Don't miss it!

An Amazing Experience

Have you ever wanted to take the wheel or hoist the sails of a real schooner? If so, here's your chance! This Bugeye Backcountry Tour is an amazing mix of sailing, snorkeling, and kayaking among the most scenic settings in the Florida Keys, including the Sponge Garden Reef and Mangrove Island. Discover the amazingly diverse ecosystem of Key West’s backcountry and observe the abundant wildlife from the water. This tour is a MUST for outdoor enthusiasts! Book your spot today!

Bugeye Schooner Backcountry Eco Tour

Have you ever wanted to take the wheel or hoist the sails of a real schooner? If so, here's your chance! This Bugeye...

The boat and ocean were great but the staff made our trip. We would absolutely return or recommend this excursion to others.

Schooner Appledore Activities

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