The Florida Keys
A 113-mile island chain from Key Largo to Key West, connected by a single highway — a unique island lifestyle with real structural tradeoffs around evacuation, insurance, and housing supply.
Retiring in the Keys means accepting tradeoffs most of Florida doesn’t carry: a single hurricane-evacuation road (US-1), some of the highest housing and insurance costs in the state relative to a small housing stock, and a slower, tourism-and-fishing-based island economy — in exchange for a setting genuinely unlike anywhere else in the country.
Who Fits This Region
- Retirees drawn specifically to island living, diving, and fishing culture who accept the tradeoffs involved
Who May Prefer Another Region
- Retirees concerned about hurricane evacuation logistics, insurance costs, or limited housing supply
Major Tradeoffs
- A singular island lifestyle versus a single evacuation route, high insurance costs, and a small, expensive housing stock