Best 769 things to do in Big Pine Key, FL

Cast for big fish with a seasoned Key West captain

Fish South Florida waters with Captain Magnus aboard the Ultra Grand Slam

Private fishing for your Key West group, with gear and fish cleaning included

Cruise Key West’s seaport by tiki boat with captain-guided local stories

Learn sailing fundamentals aboard Hobie Wave catamarans

Circle Key West in 90 minutes on a thrilling 26-mile guided jet ski ride.

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 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 a 1939 wooden schooner and take a turn at the helm

Sail a 1930 schooner into the Key West sunset

Sail Key West aboard a 1939 wooden schooner with captain and crew

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

Paddle mangrove tunnels, enjoy a picnic, and look for Key Deer

Fish Key West’s shallow backcountry waters from a stable, low-draft boat

Walk Hemingway’s Old Town haunts with a guide in 65 minutes

Customize your Downtime on a tritoon charter for just 6 guests

See Key West's canal-front homes as evening settles over the water

Swim and snorkel at Key West sandbars with a licensed captain and included gear

Cruise Key West sandbars with a local captain; includes snorkel gear, floats, and room for up to 10

Explore a preserved Civil War-era fort with one-day admission

Visit the Tennessee Williams Museum during daily open hours