key west florida weekend guide 2024

 (Updated 2024)

We lived in the Florida Keys for two years and frequently go back for weeks at a time. It is one of our favorite places in the United States, and we want to share our favorite places and must-stops with you! You can click the map to be taken directly to our Roadtrip guide.

Here is everything we suggest for an unforgettable Key West, Florida, weekend.

Day one:

Coffee at Cuban Queen, Hemingway House, Fort Zachary State Park. (bring a packed lunch) A great sandwich shop is just around the corner from the park-Little White House Subs.

Relax in the hot tub before preparing for a special dinner at Little Pearl.

If you're up for it, head over to Duval Street, where you can bar hop with the parrot heads and catch some live music from various local artists.

Day 2:

Breakfast at Blue Heaven

Southern Most Point (get there early before the crowd)

Smathers Beach

Dj's Clam Shack for Lunch

Key West First Legal Rum Distillery 

Shopping on Duval

Sunset Cruise 

Dinner at Santiago's Bodega