Tours And Adventures in Big Pine Key, FL

Light up the sea floor on a guided kayak paddle beneath the stars

Climb 88 steps for panoramic island views and explore the Keeper’s Quarters Museum

Cruise to a Key West sandbar for swimming, relaxing, and wildlife watching

Snorkel Sombrero Reef with gear included on the Marathon Mermaid

Reef fishing for snapper and grouper, with bait and tackle included

Parasail above Key West on a 12-passenger boat with tandem flight options

Charter a private 2-tank dive with an in-water dive master

All-day Smathers Beach pass with parasail flight and unlimited watersports

Play 1,700+ virtual courses with real-time swing data

Paddle calm, shallow waters with glass-bottom views of illuminated marine life

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

Paddle clear waters and mangrove tunnels with an eco-guide

Cruise to Fort Jefferson and swim in Dry Tortugas waters

Brunch, drinks, and a swim stop aboard a Key West sail

Sail turquoise waters as Key West’s sunset colors emerge

An evening cruise with champagne, music, and sunset views from the water

Cruise Key West's calm harbor channels on a private sunset charter

Private Key West sunset cruise for up to 6 on the Miss Marie

Cruise Key West by private boat with snorkel gear and a sandbar stop

Enjoy a four-hour private cruise to mangrove sandbars with snorkeling, paddle boards, and a catered Cuban lunch.

Backcountry flats fishing for up to 4 anglers on the ShadowCaster

Shape your fishing day around reef, wreck, or offshore waters

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

Choose a 3–6 hour private sandbar charter with floats, snorkel gear, and shade