Best 859 things to do in Sugarloaf Key, FL

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

Relax as a private guide reveals Key West’s history, culture, and architecture

Explore Key West’s history, culture, and early industries on a small-group walk

Walk Key West’s historic streets and uncover the stories behind its landmark buildings

Sunday sailing with brunch bites and bottomless mimosas

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

Visit the Tennessee Williams Museum during daily open hours

Sip fine wines and craft beers on an intimate schooner sail as the sun sets off Key West’s coastline

Explore Boot Key Harbor with a champagne toast at sunset

Twin 200 HP power for independent Florida Keys boating

Take the helm of a 22-foot pontoon with a 115-horsepower Suzuki engine

Set out with fishing and navigation gear aboard a 19-foot boat

Explore Marathon waters aboard a well-equipped 21-foot center-console boat

Take the helm of a 24-foot SeaHut for Florida Keys cruising

Cruise by catamaran to Money Key for beach time and flat snorkeling