On a winter weekend getaway to Miami, we set aside two days to drive down to Key West. Travel time aside, we had roughly 24 hours to enjoy this laid-back island city.
The drive to Key West is beautiful and while it’s understandable if you’re eager to get to Key West and want to minimize stops, I recommend stopping at the cutest tiki bar (Holiday Isle, rumored location of Kokomo) on Islamorada. Nothing like a good rumrunner to make you feel like you’re really in the Keys.
Once you make it to Key West, a few must do’s:
- Walk Duval Street
- Visit Hemingway’s House
- Savor key lime pie at Kermit’s (seriously, so good!)
- Relax at Fort Zachary State Park
- Check out the Southernmost part of the United States (yes, it’s touristy, but still a fun photo opp)
- Rent a bike to explore the island (biking Key West is an ideal way to see as much of the island as possible if your stay is short)
When the sun begins to set, head to Mallory Square for the nightly sunset celebration. Each night, dozens of people line up on the pier to watch the sun set, cheering when it finally sinks into the skyline.
End your day by grabbing at drink on (or near) Duval Street at:
- Sloppy Joe’s (former Hemingway haunt)
- Green Parrot (low-key dive bar)
- Martin’s (great martinis)
- Willie T’s (fun live music)
In the morning, begin your day with breakfast al fresco with the roosters at Blue Heaven, the most darling island spot. The pineapple pancakes are to-die-for, and you can’t leave without having a slice of sky-high key lime pie.
If you’re visiting the Keys for beach time, I’d recommend driving 40 minutes outside of Key West to Bahia Honda State Park on Big Pine Key. Secluded white sand beaches, crystal-clear turquoise water and fewer crowds make it a great place to relax for a few hours before leaving the Keys.