Best results for Summerland Key Florida

Explore sandbars, snorkeling spots, and fishing areas by boat

Get out on the water aboard a shaded 24-foot deck boat

Enjoy a durable floating water mat for family time on the water

Learn scuba basics and make two guided reef dives in one day

Fish for snapper as twilight settles over Key West waters

A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

Paddle the mangroves and snorkel with a small group in the Key West National Wildlife Refuge

Snorkel the reef, visit a sandbar, and sail into sunset on a spacious catamaran

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Charter a sailboat in Key West for up to 42 guests

Sail into a Key West sunset while searching for bottlenose dolphins

Raise a glass to the year's final Key West sunset with a live DJ and unlimited drinks

Sail Key West on Schooner America 2.0 with complimentary soft drinks

Sail into the Key West sunset with drinks and hors d'oeuvres included

Sail Key West's night waters beneath the full moon aboard a 105-foot schooner

Join Key West's holiday flotilla aboard a decorated schooner with drinks, bites, and onboard festivities

Sing along with live holiday music aboard a festively lit schooner

Sail Key West’s waters aboard a 105-foot schooner with Christmas brunch and drinks

Sail Key West’s Atlantic coast at sunset aboard a historic schooner

Take the helm or relax beneath the sails on a private classic schooner

Book a private Florida Keys backcountry and flats fishing charter

Enjoy live songs from stage, screen, and radio with Miss Bouvee's adult-humor performance

Sail Key West’s historic waterfront aboard a hand-built 86-foot schooner

Explore Islamorada's Theater of the Sea on a Florida Keys road trip