3 to 4 Days in Key West: Old Town Icons, Fort Zachary Taylor & Dry Tortugas

This itinerary is designed so that Days 1, 2 and 3 require no car inside Key West (using a rented cruiser bike and the complimentary Duval Loop bus), while an optional Day 4 covers the Overseas Highway stops on your drive to or from Miami.

Day 1: Southernmost Point, Hemingway Home, Truman House & Mallory Square Sunset

• Early Morning: beat the queue by cycling to the Southernmost Point Buoy soon after sunrise, then visit the Key West Butterfly Conservatory two blocks north.
• Late Morning: walk up Whitehead Street to the 1851 Ernest Hemingway Home (cash only; meet the 60 six-toed cats) and climb the 1848 Key West Lighthouse across the street, followed by brunch and meringue Key Lime Pie at Blue Heaven in Bahama Village.
• Afternoon: see the Mile 0 Sign, tour the Harry S. Truman Little White House, and lift a 1622 gold bar at the Mel Fisher Maritime Museum.
• Evening: join the Mallory Square Sunset Celebration, stroll the Historic Seaport and Duval Street, and dine on Cuban roast pork at El Siboney.

Day 2: Coral Reef Snorkel, Fort Zachary Taylor Beach & Schooner Sunset Sail

• Morning: board a catamaran at the Historic Seaport for a Coral Reef Snorkelling Trip to Sand Key (or a Backcountry Kayak & Sandbar Tour), followed by chocolate-dipped Key Lime Pie at Kermit's.
• Afternoon: cycle with water shoes into Fort Zachary Taylor State Park to tour the 1845 fortress and snorkel the rock jetties under the Australian pines.
• Evening: sail on a wooden schooner (like America 2.0) at sunset, or take the launch to Sunset Key for dinner at Latitudes.

Day 3 (and Day 4): Dry Tortugas National Park & The Overseas Highway

• Day 3: take the Yankee Freedom III Ferry or Seaplane 70 miles west to Dry Tortugas National Park to walk the moat wall, tour Fort Jefferson and snorkel.
• Day 4 (Overseas Highway): spot Key Deer on Big Pine Key (MM 30), swim at Bahia Honda (MM 37), walk the Old Seven Mile Bridge (MM 47), and feed tarpon at Robbie's of Islamorada (MM 77.5).