Picture of a sunset sail aboard the Jolly Rover, near Key West, Florida

The sun sets over the Jolly II Rover, docked in Key West.

Photograph by Steven Martine, National Geographic Travel

By Maryellen Kennedy Duckett

Taking a sunset sail is arguably the perfect ending to any Florida day. Sails billow in the breeze. The sky glows a fiery orange before dissolving into pinks and purples. Your boat chases the sun until it disappears below the horizon or "sizzles" into the water. Sunset cruises typically leave the marina in late afternoon and include optional adult beverages to toast the day.

Jolly II Rover, Key West

When the Jolly II Rover sails out of the Historic Seaport at Key West on its daily sunset cruise, people on shore and on passing boats stop in their tracks to take notice. The magnificent, square-rigged tall ship, an early 1800s American coastal schooner replica, boasts distinctive red sails. For many locals and visitors, experiencing at least one sunset from the deck of the Jolly II Rover is a Key West rite of passage. Weather permitting, the ship's two-hour Red Sails in the Sunset cruise operates every day, and every trip includes a booming cannon salute and the opportunity to help hoist the sails.

Kai Lani Charters, Clearwater Beach

Custom designed and built in Clearwater, Kai Lani is a 50-foot-long and 30-foot-wide catamaran owned and operated by locals Captain Mike Judge and his wife, Claire. A canary yellow, 64-foot-tall mast makes the Kai Lani easy to spot when the boat is docked in bustling Clearwater Beach Marina or when it's gliding through the Intracoastal Waterway on its way to catch the sunset in the Gulf of Mexico. "Kai Lani is a one-of-a-kind boat," says Claire, who serves as crew, guide, and host on every trip. "A unique, rotating wing mast creates a more efficient and smooth sail, and the open bar area gives a party feel to any sail."

Miami Sailing Adventures, Miami Beach

Sailing into the sunset South Beach-style is a luxurious, tailor-made experience. Agata Pozniak, owner of Miami Sailing Adventures, designs fully customized trips aboard private sailing yachts, accommodating 2 to 12 passengers. Sunset sails can include dinners prepared fresh on board, swim stops, and opportunities to take the helm and learn from the captain. The specifics—such as start time, duration, and either blue water (ocean) or calm Biscayne Bay water sailing—are up to you. "Most sunset sails finish with amazing views of the Miami skyline by night," says Pozniak. "We depart from South Beach, so you'll see South Pointe, Fisher Island, Port of Miami, downtown Miami, and Virginia Key. The sunset views are either on Biscayne Bay or on the ocean along South Beach. You don't have to be a sailor to join us. In fact, most of our guests are on a sailboat for the first time."

Practical Tip: Sunset sails are popular year-round. Advance reservations always are recommended.


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