Best 316 things to do in Summerland Key, FL

Enjoy a customizable cruise through Florida Keys sandbars with snorkel gear and coolers included.

Spot playful dolphins and snorkel vibrant reefs on a small-group Key West cruise

Sail into the Key West sunset with fresh sushi and drinks

Private Barefoot II charter for up to 6 to snorkel and relax in the Florida Keys

Spend 8 hours fishing deeper into Key West’s backcountry waters

Fish Key West backcountry waters on a 4-hour charter

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

Sail a small-group catamaran to snorkel reefs and look for wild dolphins

Adults-only Key West sunset sail with champagne and gourmet cheese

Charter Cowfish for a 4-hour private cruise with any two water activities

Private Key West sunset sail with your music and a flexible start time

Sail Key West waters on a private 4-hour charter for up to six guests

Spend a full day sailing from Key West with up to 6 guests

Charter The Coolwater for a Key West–style fishing trip for up to 6 people

Dolphin watch, snorkel, and visit a sandbar on a small-group Key West tour

Charter COWFISH for a Key West sandbar stop and guided snorkel, with snacks and water included

Private 4-hour kayak, snorkel, and sail trip for up to 6 in Key West

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

Ride a jet ski around Key West with 5–6 scenic stops and a free shuttle

Parasail from Smathers Beach with a 10–12 minute flight and up to 1 hour on the boat

Enjoy a high-flying 10–12 minute parasail ride with sweeping views of Key West

Snorkel Key West’s vibrant reef aboard a fast catamaran with breakfast and post-trip drinks.

Captain a two-person boat to secluded sandbars and mangrove islands.