Key West is the end of the road—literally—and a launch point for the Dry Tortugas, a submerged preserve 70 miles offshore. This trip combines the bohemian nightlife and conch-salad culture of Key West with world-class snorkelling at Fort Jefferson and pristine reefs where few tourists venture.
Arrive in Key West; settle into Old Town near Duval Street.
Walk Duval's galleries, vintage shops, and Sloppy Joe's Bar where Hemingway drank.
Watch sunset at Mallory Square Dock; dinner at Latitudes, a beachfront tiki bar on Sunset Key (ferry across).
Board the Yankee Freedom ferry (2.5 hours) to Fort Jefferson at sunrise.
Snorkel the northern moat wall and shipwrecks; tour the fort's Civil War barracks.
Return to Key West; light dinner and early rest.
Take a small-group boat to the Marquesas Keys' shallow gardens; snorkel three different sites.
Cruise past mangrove islands and spot rays, nurse sharks, and grouper.
Return to Key West; dinner at Santiago's Bodega for Spanish tapas and live flamenco.
Visit Fort Zachary State Park; snorkel the wreck of the Windjammer off its beach.
Explore the fort's Civil War history and powder magazine; relax on the beach.
Visit Kermit's Key Lime Pie Shop for fresh pie and key lime cocktails; stroll the Key West Butterfly Conservatory.
Leisurely breakfast at a café on Whitehead Street; last-minute shopping.
Visit the Ernest Hemingway Home & Museum, a quirky colonial mansion with six-toed cats.
Depart or stay for sunset sailing.