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Windjammer Champagne Sunset Sail

Windjammer Champagne Sunset Sail -

Experience sailing on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger windjammer. At only 49 passengers, her decks are spacious and comfortable.

The Appledore II is the second in a series of historic schooners commissioned by the Smith family to travel the world. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

Appledore II is no pampered ship, she sails year-round. Summers are spent sailing around Camden, Maine and winters are here in tropical Key West. Twice a year Appledore II sails the 2,000 mile ocean voyage between her two homeports. Some of the crew on your tour have made this exciting journey – ask them about their adventures.

Sails flying in the wind, you leave behind the Historic Seaport and head out to the Atlantic. Soon there is wind in your hair and the warm, tropical salt air kisses your face. Take in the view as the schooner navigates her way past Key West’s Harbor, Mallory Square, the Navy Mole, Sunset Key and historic Fort Zachary Taylor.

Quench your thirst with complimentary homemade sangria, boutique wine, frosty cold premium beers, full cocktail bar, soft drinks and water.

While there is abundant marine life under the water, there is also plenty to see on the water’s surface or circling in the blue sky above you. A pod of dolphins may surface or you might spot a turtle floating by. Perhaps an osprey will plummet down to the water to catch its lunch or a pelican will make a splash landing near the vessel.

With the Historic Seaport drawing closer, your schooner sail cruise is nearing its end. Life is good in paradise.

Join us on Friday April 28th for a SPECIAL EVENT! 

Friday, April 28th, 6:30PM

41st Annual Reenactment of the great sea battle of the Conch Republic

Join us for participation in this large scale, hilarious harbor battle pitting the Conch Republic’s Military Forces (Air Force, Army, and Navy) and Privateers of all shapes and sizes against their valiant foe, non-other than a United States Coast Guard Cutter. The good-natured foes represent the USCG Cutter Diligence, attacked on Apr. 23, 1982, by the Schooner Western Union, the first Flagship of the Conch Republic.

Note: Guests WILL GET WET from water cannons used in this reenactment. Also, beverage service may be slightly less than normal as the crew participates in the battle!


Boarding Starts 1/2 Hour Before. Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. All prices do not include Florida sales tax.


  • Sail Past Local Key West Landmarks
  • Take Part in Hoisting the Sails and a Turn at the Wheel
  • Home-made Sangria, Boutique Wine, Premium Beer, Full Cocktail Bar, Soft Drinks and Filtered Water

Wide decks with room to walk around
Generous seating

Only 49 passengers for an intimate sail

A spacious head (bathroom)


Grab your hat, sunglasses, camera and love of adventure. We will do the rest!

Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. iles long, you can easily view all of Key West from the air. Look for famous landmarks like the Historic Semingway Home, Key West Lighthouse, Mallory Square where the Sunset Celebrations are held, U.S. Coast Guard Cutter Ingham Maritime Museum, Harry S. Truman Little White House, Martello Towers on Higgs Beach, Fort Zachary Taylor, Southernmost Point, and Smathers Beach.

As you ascend you acquire a birds-eye view of paradise where on a clear day you can see for 12 miles. The tropical waters around Key West are teeming with wildlife and you can often spot fish, turtles, rays and dolphins. Look for Sunset Key where the rich and famous live, Wisteria Island, the Key West Naval Station on Stock Island or a cruise ship making its way to port.

Parasailing is great for the whole family, including children 6 years and older. No experience is necessary – Sebago’s professional crew provide you with instructions and make sure you are secure and comfortable in your harness before your smooth take-off. Our modern boats with their extended platforms allow gentle, dry landings. Let the crew know if you want your ride to be mild and dry or wild and wet!

Your parasail adventure is an hour long making it easy to add on to your Sebago tours or fit into your other Key West activities.




Smiling Girl
AGES 4-11:


Baby Boy

No Charge


2 Hours



Boarding Starts 1/2 Hour Before. Spring and Fall times vary by the sunset – please check with us for exact departure times. Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. All prices do not include Florida sales tax.

Windjammer Sunset Sail includes

  • Sail Past Local Landmarks as you Enjoy a Famous Key West Sunset
  • Champagne, Sangria, Boutique Wine, Premium Beer, Fine Liquors, Soft Drinks and Filtered Water