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Windjammer Classic Sunset Sail

Windjammer Classic Sunset Sail -

The perfect Key West sunset sail. Picture yourself on the deck of a romantic 2-masted wooden schooner. Wind blowing in your hair, the tall ship sails into the sunset over the southernmost point of the U.S.

Key West sunsets are best appreciated from a Sebago ship. Sebago’s tall ship was hand-built in the tradition of schooners since the 1800s. This 86’ windjammer has circumnavigated the globe. Today the Appledore II gracefully skims into the Atlantic in search of the perfect sunset.

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.

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.

With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of bubbling champagne or boutique wine, tropical home-made sangria, an icy cold premium beer, full cocktail bar or soft drinks. Chef’s Selection of Hors d’oeuvres & Cocktail Shrimp complete the perfect evening.

As the sun begins its fiery descent into the Atlantic, your captain carefully maneuvers the Appledore II into position to maximize your view of the setting sun.

Start your own Key West tradition tonight – a sunset sail Key West style on the historic Appledore II schooner will forever linger in your memories.

You will be sailing on Sebago's Appledore II, a two-masted 86' windjammer featuring:

Wide decks with room to walk around

Generous seating

Only 49 passengers for an intimate evening

A spacious head (bathroom)

What To Bring

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.



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.


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