Key West
United States (Florida)
"Laid-Back Island Life at the Southernmost Point"
Key West sits at the end of the Overseas Highway, closer to Havana than to Miami. Duval Street buzzes with bars and shops, while quiet lanes of conch cottages lead to the Hemingway Home and its six-toed cats. Every evening the crowd gathers at Mallory Square for sunset buskers. Snorkel and dive trips head to the only living coral barrier reef in the continental US, and Dry Tortugas National Park is a full-day ferry or seaplane adventure.
Southernmost Point buoy, Mallory Square sunset, Duval Street, Ernest Hemingway Home, Dry Tortugas National Park, reef snorkeling, Key Lime pie tasting, Fort Zachary Taylor
December–May
Rent bikes instead of driving; book Dry Tortugas ferry early; Duval Street gets rowdy late, so families stay on quieter ends
A popular Western Caribbean cruise port and a fun Florida road-trip finale. Sell for sunsets, snorkeling, and easy relaxation.
2–4 days
$200–$400
📍 Southernmost Point buoy in Key West with the ocean behind