Best results for Big Pine Key Florida

Sail into the Key West sunset with drinks and hors d'oeuvres included

Private 2-hour sail on a 1939 wooden schooner in Key West

Catch the Key West sunset on the historic schooner Malabar X

Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

Book a private Florida Keys backcountry and flats fishing charter

Cruise Key West at sunset on the Lazy Lady tiki boat with a premium open bar

Backcountry flats fishing for up to 4 anglers on the ShadowCaster

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

Learn sailing fundamentals aboard Hobie Wave catamarans

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