Wind & Wine Sunset Sail

Savor fine wines and the amazing Key West sunset on our Wind & Wine Sunset Cruise, a unique experience rated #1 Thing To Do in Florida on for many years.


The original Wind & Wine Sunset Sail by Danger Charters lets you experience the spectacular Key West sunset while enjoying fine wines, premium beers, and delicious appetizers aboard an authentic 65ft skipjack sailing schooner. This top-rated sunset cruise leaves Key West in the evening and glides toward the horizon under a cloud of sail to provide an unforgettable adventure at sea. 

The Island’s Top Sunset Cruise
Coastal Living Magazine has ranked the Danger Charters Wind & Wine Sunset Sail as one of the top two sunset cruises in America. We have been honored with a Trip Advisor #1 rating for three consecutive years. No other cruise line can match the grace and beauty of our custom-built 65-foot schooners, replicas of the classic skipjacks used by 19th-century Florida Keys wreckers and fishermen. 

And the Wind & Wine Sunset Sail earns praise from wine lovers because it presents a selection of fine wines from around the world – it is one of the only U.S. sailing excursions that offers “real” wine for your tasting pleasure. You can pair your favorites from among 8 wines (usually 4 red, 3 white, & a champenoise) and 5 premium beers with palate-cleansing and flavorful gourmet treats including Havarti Dill, Smoked Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Brie, Green Apple with a Honey Drizzle, and more.

Enjoy an Amazing Key West Sunset
Sunset in Key West is world famous, and has been attracting the attention of artists and writers for nearly two centuries. The colors are incredible, changing by the minute and never the same from day to day. Depart the harbor on a graceful schooner as evening lowers. Savor the cooling breezes while blue water laps the hull as the ship glides smoothly away from Key West. Then lift your glass with loved ones and new friends as the sun seems to pause just over the horizon and the sky lights up.

The schooner moves almost silently across the water and provides an undisturbed view as the sun turns red and touches the water, or sinks behind lowering clouds that meet the sea. The sky flames with red, orange, and purple as the party goes silent, cameras click, and lovers hold each other close. Of all the fun activities you will enjoy during a Key West visit, this is the one you will remember for years. It is a beautiful way to end a perfect day in Key West, and an excellent happy hour start for an evening on the town.

Book the Ultimate Key West Sunset Cruise
A tropical sunset cruise is always something special, and sunsets in Key West are so incredible that they have been officially celebrated since the late 1960s. There is nothing better than viewing the grand spectacle from the deck of a sailing vessel with wind over the water cooling the air and no obstructing buildings or traffic noise to block the view or break the mood. A small party in a casual setting aboard a lovely sailboat, soft tropical music, and a variety of fine wines, quality beers, and delicious hors d’oeuvres make this sunset cruise a true connoisseur treat that is sure to be a highlight of your Key West visit.

A Danger Charters Wind and Wine Sunset Sail is a Key West vacation must-do for all lovers, wine lovers, and sailors. Secure online booking at the click of a button makes reservations simple, quick, and convenient. Plan ahead and reserve your sailing date now because these popular Key West sunset cruises fill up very quickly.

#1 Rated Wind & Wine Sunset Sail

Cast off with Danger Charters aboard a 65ft skipjack schooner to sail the nearshore waters of Key West and watch the sky blaze with color as the sun sinks below the horizon. The unique Wind & Wine Sunset Sail has earned #1 ratings from Coastal Living Magazine and Trip Advisor for the beauty of the sailing vessels and the great selection of fine wines and premium beers complemented with an array of gourmet appetizers.

Private Wind & Wine Sunset Sail for up to 30 Guests

Enjoy the yachting lifestyle with a 65ft skipjack sailing schooner reserved exclusively for your use on the Danger Charters Private Sunset Sail. A full selection of 8 fine wines and 5 premium beers along with a delectable array of gourmet appetizers make this private charter truly unique. Celebrate your special occasion with the spectacular beauty of the Key West sunset aboard the island’s top-rated sailing cruise.

  • Sail into the Caribbean sunset aboard a classic 65ft schooner.
  • Watch the crew hoist the sails as we get underway.
  • Enjoy 8 different wines from around the world – taste them all or choose your favorites.
  • Sample 5 premium import & domestic beers.
  • Pair your beverages with gourmet appetizers including Havarti Dill, Smoked Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Brie, Honey-Drizzled Green Apple, and more.
  • Relax in a fun atmosphere with a background of tropical music.
  • Mingle and meet new friends or spend a romantic evening with someone special as the sun melts into the sea.


Current Specials

Use code ALLABOARD and save 10% off all day trips during January when you book online! (Excludes all Private Charters)

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