Things to Do in Key West

By VI | Disclosure: I use affiliate links

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Whenever I need a dose of sun, salt air, and that laid-back island vibe, I head straight to Key West—and I think you should too. There’s something about those colorful streets, the history that lingers in every corner, and the way the sky lights up at sunset that always pulls me back. Whether you’re into Hemingway’s old haunts, coral reef snorkeling, or just kicking back with a mojito, you’ll find your kind of paradise here.

Best Time to Visit

I’ve found the sweet spot is March to May. You’ll get warm weather without the winter crowds, and hotel rates tend to ease up a bit. I’ve gone in winter too—it’s gorgeous, just busier and pricier. If you’re looking for deals and don’t mind rolling the dice on weather, September and October can be surprisingly peaceful (just keep an eye on the forecast—hurricane season runs June through November).

How to Get There

By Plane: I usually fly right into Key West International Airport (EYW). It’s small and easy, with direct flights from places like Miami, Atlanta, and Charlotte. You’ll be in vacation mode the second you land.
By Car: If you’ve got the time, drive down the Overseas Highway. I’ve done the 3.5-hour route from Miami, and you won’t believe the views. You’ll want to stop along the way—it’s part of the adventure.
By Ferry: I’ve also taken the Key West Express from Fort Myers. If you like the idea of arriving by sea, you’ll love this option. It’s scenic, relaxing, and drops you right near Old Town.

Where to Stay

Perry Hotel Key West – I’ve stayed here when I wanted peace and quiet. You’ll love the marina views and the chill, waterfront vibe.
The Reach Key West – If you’re craving a bit of luxury, this beachfront resort is perfect. I’ve lounged on the private shoreline here, and you’ll appreciate the upscale feel without it being too formal.
Heron House – For something romantic and low-key, I always suggest this adults-only inn. You’ll feel like you’ve discovered a little tropical hideaway right in Old Town.
Southernmost Beach Resort – I’ve recommended this spot to so many friends. It’s got pools, beach access, and those island-chic rooms that make it hard to leave. You’ll be right where the action meets the ocean.