things to do in Big Pine Key, FL

Charter a private historic schooner sail with drinks and snacks included

Sail, snorkel, and toast with included drinks aboard a spacious catamaran

Private reef time aboard a 30-foot Jeanneau yacht

Set your own fishing pace with a private captain

Search Key West skies with military-grade night vision

Sunset catamaran sail with live music, appetizers, and included drinks

Share a 4-hour fishing charter and meet fellow anglers in Key West

Toast the sunset on a scenic evening cruise with drinks and appetizers

Sail, kayak, and snorkel Key West's shallow waters on a private cruise

Circle Key West by jet ski with guided stops and free-ride time

Private Key West sandbar charter with snorkel gear, drinks, and snacks

Hunt reef fish alongside a professional divemaster and refine your underwater skills.

Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

Sip bubbly and sail into the Key West sunset aboard a spacious catamaran

Cruise between waterfront tiki bars and restaurants with a private captain

See Key West and the Seven Mile Bridge on a 60-minute scenic flight

Investigate haunted artifacts and cold cases inside a historic Key West firehouse

Dolphin watch and backcountry snorkel with complimentary drinks

Split a 4-hour party fishing charter with up to 14 people

Design a Key West charter around your group’s occasion

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

Circle Key West by Yamaha WaveRunner with landmark and sandbar stops

Build your own 3–3.5 hour private boat charter with snorkeling gear, snacks, and drinks

Ride in comfort on the gyro-stabilized Park Shark to Dry Tortugas