Dating in Key West
In shortKey West is small, so people tend to run into each other. Locals and visitors mix every evening on the waterfront. If you live in the Keys, be open to dating a little further up the islands.
A first date idea
Sunset Celebration at Mallory Square
The Sunset Celebration happens every night and starts about two hours before sunset. Musicians, jugglers, magicians and high-wire acts perform while local artists sell their work. Watch the sun set into the Gulf, then walk on for dinner.
Source: Mallory Square: Sunset Celebration, checked 8 November 2026
Join the nightly crowd at Mallory Square to watch the sun go down.
For more ideas, read cool-season dates in Florida or dates for a Florida summer.
