☀️ 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

View of palm trees swaying above a hotel pool in Key West, capturing the relaxed island atmosphere.

🏖️ 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.

Signature Painkiller cocktail served with fresh fruit garnish at the Rum Bar on Duval Street in Key West.

🍹 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.

Vibrant rooster walking through a local market street in Key West, showcasing the island’s famous free-roaming chickens.

🐓 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-topped pizza from Seaside Café in Key West, known for its beachfront dining and tropical vibes.

🍕 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.

Peaceful sunset sail on the Schooner America 2.0 in Key West, with golden light reflecting off the ocean.

🌅 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.

🥧 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.

Fresh Florida stone crab claws with mustard sauce at Half Shell Raw Bar

🦀 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.

Planning a Visit?

If you're dreaming about your own Key West trip, check out the Key West Travel Guide for insider tips, food finds, and itinerary ideas — or explore the Key West Boutique Hotel Guide for the most charming places to stay.

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.

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