Plan a destination trip with practical guidance on timing, flights, stays and vacation options. This page is designed to help travelers prepare questions, understand common decision points and connect the topic with the wider trip.
Choose the right travel period
Key West stays warm year-round; winter (December–April) is the most requested season, while hurricane season runs June through November.
Flight and airport planning
Key West International (EYW) has limited direct flights; many travelers instead fly into Miami or Fort Lauderdale and drive the Overseas Highway, about 3.5–4 hours, or book a connecting flight.
Where to stay
Old Town keeps Duval Street, Mallory Square and the nightly sunset celebration walkable; New Town offers more resort-style properties a short bike or trolley ride away.
Build a practical itinerary
Most visitors plan 3–4 nights, enough time for Duval Street, a sunset sail and a day trip to the Dry Tortugas if desired.
Frequently asked questions
How long should I stay?
The ideal duration depends on travel style, distance and planned activities.
Should I book flights and hotels together?
Comparing them together can help ensure schedules and availability align.
Are flexible dates useful?
Yes. Flexible dates may improve flight, hotel and package options.
Related planning resources
Planning a new trip?
Compare eligible flight, hotel and vacation options with an independent travel specialist.