☀️ My Kind of Island: A Key West Photo Journal
Some places just get under your skin. I first visited Key West on a cruise and knew before I got back on the ship that I needed more time. It’s got a Caribbean vibe but stays connected by Highway 1. Island time meets street art, beach bars, and the kind of live music that spills out of doorways. People say “One Human Family” here and mean it.
This isn’t a hotel guide (though here’s one if you want it). It’s a look at what Key West feels like through moments, not checklists. Key West lives on its own time, and somehow, it always manages to reset mine.
My Favorite Key West Moments
🏖️ Pool time at the hotel
Give me a shady lounger, a paperback, and a pool surrounded by palms. I don’t care if I’m staying at a five-star resort or a funky guesthouse — this is island luxury.
🍹 A Painkiller at the Rum Bar
There’s no judgement here at the Rum Bar. The Painkiller is part coconut, part nostalgia, part “sure, why not.” This little bar on Duval is one of my go-tos for strong drinks and stories.
🐓 Chickens in the street
Roosters and hens crossing the road isn’t a joke in Key West — it’s just life. You’ll find them strutting through parking lots, crowing in alleyways, and generally running the place.
🍕 Lobster pizza at Seaside Café
Touristy? Sure. But sitting by the beach with a slice of lobster-topped pizza (they even have Gluten Free) and a mojito in hand feels like the right kind of cliché.
🌅 Sunset sail on the America 2.0
This isn’t your average booze cruise. The schooner America 2.0 is peaceful, elegant, and one of the best ways to see the sun melt into the Gulf. The sails go up, the snacks come out, and everything else fades.
☕ Morning Cuban Coffee Queen run
Nothing wakes you up like a Cuban coffee from this colorful little stand. Bonus: their breakfast sandwiches are also worth the wait.
🥧 Best key lime pie? Still Blue Heaven
I know the debate rages on, but there’s something unbeatable about Blue Heaven’s meringue-topped pie — especially if you’re sitting under the banyan tree with chickens at your feet.
🦀 Stone crab in season
If you’re visiting between October and May, do yourself a favor and order the stone crab. Sustainably harvested and incredibly sweet, it’s a Florida delicacy that tastes even better with mustard sauce and an ocean view.
Nearly all Key West seafood restaurants have them while in season. One of my favorites is the Half Shell Raw Bar.
🐠 1930s Key West Aquarium
It’s tiny, historic, and wildly charming. You’ll find sea turtles, sharks, and exhibits that haven’t changed in decades — in the best way. It’s one of the oldest aquariums in the country.
🏰 Fort Zachary Taylor
A dose of island history, shaded walking paths, and some of the best ocean views in Key West. Pack water. Take photos. Stay awhile.
👻 Robert the Doll
If you’re feeling brave, visit Fort East Martello and meet Robert the Doll. Supposedly haunted and definitely unsettling, he's one of Key West’s quirkiest legends — and not for the faint of heart. No, I didn’t take his photo.
Planning a Visit?
Want to plan your own island escape? My Key West Travel Guide covers where to eat, what to do, and hidden gems to seek out. And if you’re into stylish stays, this boutique hotel guide rounds up my favorites.
One Last Thought
I’ve been to dozens of islands, but this one always stays with me. I don’t come for big plans. I come for the way this place makes you breathe differently. Slow down, look around, and let yourself be part of it. That’s the real magic of Key West.
Got a favorite moment from Key West? Drop it in the comments or tag me on Instagram @Inspiration_Uncharted.
