Best results for Summerland Key Florida

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

Fish, dive, and explore the Florida Keys with onboard navigation and water access

Twin-engine power, fishing features, and free delivery for your time on the water

Cruise, fish, snorkel, or dive with easy water access

Offshore-ready weekly boat rental with twin Yamaha power

Snorkel Coffins Patch Reef, then swim and relax at Valhalla Sandbar

Private Coffins Patch snorkel plus Valhalla Sandbar swim in 3.5 hours

Snorkel the reef, unwind at Valhalla Sandbar, and enjoy a Florida Keys sunset cruise

Snorkel the reef, relax at Valhalla Sandbar, then cruise back at sunset

Choose reef snorkeling or a Valhalla Sandbar swim on a private 2-hour charter

Snorkel and relax in shallow water at Valhalla Sandbar on a 2-hour boat trip