Things to do

Tours & History

Key West's history is compact enough to explore on foot but layered enough that some context helps. Start with one subject you actually care about instead of trying to tour every historic house.

Find your kind of outing.

  • Key West's stories overlap: wrecking, maritime trade, Cuban migration, cigar making, military history, writers, architecture and the island's long relationship with the sea.
  • There are several ways to approach it.
  • Walk independently if architecture and neighborhoods interest you.
  • Choose a guided walking tour when stories matter more than checking off buildings.
  • Use a trolley-style overview when mobility or limited time makes a broad orientation useful.
  • And visit individual museums when a specific subject — Hemingway, maritime history, the Civil War or local culture — is what drew you there.
  • A good history day should leave room to walk between the formal attractions. Old Town itself is part of the material.

Local context for your plans.