Key West has always been a little difficult to define. It’s part historic island town, part beach escape, part nightlife destination — and somehow none of those descriptions quite covers it.
I’ve been back several times, and each trip has looked a little different. Some days are built around the water, others around exploring Old Town, and some inevitably end with a drink somewhere that has been serving them for decades. The famous stops are part of the fun, but they’re only one piece of the island.
For such a small place, there’s a surprising amount to choose between. Hotels range from historic properties in the middle of everything to resorts with their own stretch of beach. You can spend an afternoon on Duval Street or barely see it at all. And while Key West isn’t known for sweeping Caribbean beaches, knowing where to go — and what to expect — makes a difference.
This collection brings together what I’ve learned over multiple visits, including where I’d stay, the beaches I’d choose, favorite bars and restaurants, and the places I continue to return to. Whether it’s your first trip or your fifth, there’s usually another side of Key West to find.
First-Timer’s Guide to Key West
What to know before your first trip, from where to stay and getting around to sunsets, beaches, and how to spend a few days.
Where to Stay in Key West
A closer look at the hotels I’d consider, whether you want Old Town within walking distance or more of a waterfront escape.
Where to Eat in Key West
Seafood, Cuban coffee, brunch, Key lime pie, and the places I’d put on my own list.
Historic Bars & Key West Nightlife
Old Key West institutions, live music, Irish pubs, and waterfront drinks worth knowing about.
