Classic Key West architecture.
Classic Key West architecture. Photo by David Whitley.

Key West — Florida’s quirky southernmost city — offers a unique blend of Caribbean atmosphere, literary history, and laid-back island culture just 90 miles from Cuba. These travel guides explore both the famous attractions and lesser-known experiences that make this tropical outpost special. You’ll find practical information on visiting the Hemingway Home and Museum (complete with its famous six-toed cats), touring Harry Truman’s Little White House — the presidential retreat where crucial Cold War decisions were made — and understanding what makes Dry Tortugas National Park worth the boat journey beyond the main island.

Beyond the historical sites, Key West reveals its character through activities like rum-tasting — exploring how the US’s traditional home of rum went legal — and mangrove kayaking tours that showcase the area’s remarkable marine ecosystems. The Key West Shipwreck Treasure Museum brings the city’s salvaging history to life with engaging storytelling and genuine artefacts. Whether you’re interested in literary pilgrimages, natural beauty, presidential history, or simply soaking up the distinctive atmosphere of America’s most eccentric island city, these guides provide the ticket prices, opening hours, and insider advice that helps you plan a memorable visit. More Key West travel stories will be added soon.

5 great Key West experiences to book

Classic Key West architecture.
Classic Key West architecture. Photo by David Whitley.

Why book the Key West Hop-On Hop-Off Trolley Tour?

  • 🚋 Unlimited Hop-On Hop-Off: Explore Key West at your own pace with a ticket that allows you to board and depart at any of the 13 conveniently located stops across the island.
  • 🎤 Live Narrated Commentary: Enjoy “transportainment” from expert local guides who share fascinating stories of pirates, wreckers, and the Civil War as you cruise.
  • 🏝️ Comprehensive Island Views: See over 100 points of interest, including iconic landmarks like the Southernmost Point, Duval Street, and the Ernest Hemingway House.
  • 🏛️ Sails to Rails Museum Included: Your ticket grants you free admission to this unique museum, offering a deep dive into the history of the Florida Keys and Henry Flagler’s railroad.
  • 🚶 Bonus Walking Tours: Take advantage of included guided walking tours through the Historic Seaport and the downtown area to discover hidden gems on foot.