Best results for Summerland Key Florida

Private Overseas Highway road trip with time to explore Key West

Ride the Overseas Highway with a local guide and free time to explore Key West

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

Two reef snorkel stops with a seafood boil and open bar

Sail into Key West’s sunset with complimentary drinks on board

Float, wade, and unwind at Key West’s shallow-water sandbars

Snorkel Key West’s barrier reef, then enjoy a Cajun seafood boil and open bar

Paddle shallow bay waters with snorkel gear and park access

Explore historic grounds, natural trails, and a fish pedicure

Turn Key West clues into a personalized birthday or bachelor/ette photo challenge

Customize a Key West photo challenge for your celebration

Toast Key West's sunset from a 45-foot catamaran with drinks included

Backcountry flats fishing for up to 4 anglers on the ShadowCaster

Walk Key West’s Hemingway haunts with three food tastings

Join hands-on coral nursery care and reef restoration work in Key West

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

Brunch, drinks, and a swim stop aboard a Key West sail

Sunday sailing with brunch bites and bottomless mimosas

Sail into Christmas morning with brunch, mimosas, and Key West views

Watch Key West’s holiday boat parade from a 75-foot catamaran with drinks and passed appetizers

Celebrate Valentine’s Day with cocktails, passed appetizers, and a sail through Key West waters

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

Visit the Tennessee Williams Museum during daily open hours

Fly privately above Marathon's Seven Mile Bridge and Florida Keys coastline