Solo in Key West: The Trip That's All Yours

The best travel companion you'll ever have is you.

Sleep until the light wakes you. Have oysters at 2 because you felt like it. Explore Old Town at your own pace. Sip cocktails by the pool. Set sail on a golden hour sunset cruise. End the day on your balcony with a good book. Every hour, exactly how you want it.

You're in good company traveling this way. The island sits at the end of the road, and for more than a century has drawn writers, artists and free spirits who came to work on their own terms. You don't have to produce a masterpiece to do the same. You just have to show up.

At The Marker, you're by the Seaport at the center of it all, yet tucked away enough to retreat when you've had your fill of everyone.

Photo credit: Fury Water Adventures

Is Key West good for solo travelers?

Key West is one of the best solo travel destinations in Florida because everything the trip needs is built in: walkability, open-air cafes and bars, live music around every corner, and water in every direction, from a morning swim to a sunset sail. Plenty of locals showed up here on their own once, and then stayed.

Check in, drop your bags, and walk to dinner minutes later. The walk home from almost anywhere is short, and the whole island moves at strolling speed.

Where should you eat when the table is all yours?

At the bar, on a bench, by the pool, a seat for one is always welcome.

Start steps from the resort in the Historic Seaport, where lunch is a dozen oysters on the half shell and a stool at the bar. A book next to your plate is a completely normal accessory here, and so is a second glass of something cold.

We've curated the 8 best places to eat and drink by the Historic Seaport, from waterfront restaurants to beloved dive bars and neighborhood food shacks.

What do you do with a day that belongs to no one else?

Whatever you want.

Walk or rent a bike and get ready to discover your Key West. Duval Street runs from ocean to ocean, a little over a mile, and everyone travels it once. The better version is yours: turn one block off, in any direction, where the island really reveals itself. Follow whatever catches your eye: shops, cafes, local art, gingerbread porches, white picket fences, roosters crossing in front of you, and gardens you can smell before you see them. Don't be surprised to hear yourself say, Now I know why people fall in love with this place.

Spend a morning in Jimmy Buffett's Key West. His old spots are still here, from the recording studio by the shrimp docks at the Seaport to the library where he spent hot summer days cooling off and reading island history. We've collected the hidden stories and iconic locations you might not know about, so you can wander them in any order.

Photo credit: Ivette León, @ettevi_wanderlust

Go shopping. No one is waiting outside the fitting room, and no one will talk you out of anything. The boutiques here are small and carefully curated, each with its own island style. We've rounded up the best boutique shopping in Key West so you can wander it your way.

Give art, history, and culture an hour, or a day. The museums here tell some of the island's best stories: shipwrecks and salvage fortunes, sailors and schemers, a president's winter White House, and the legendary author and his six-toed cats. Linger where the story pulls you in, and move on when it doesn't.

The Key West Butterfly & Nature Conservatory fills a glass dome with hundreds of free-flying butterflies, colorful exotic birds, and two resident flamingos who act like they own the place. A couple of blocks away is the Southernmost Point Buoy, where you'll want that photo that says I was here. Stop at Southernmost Beach Cafe for a quick bite and Atlantic Ocean views, then continue on to the Key West Garden Club, which keeps a tropical garden inside the old West Martello Fort, with more ocean views worth the pause. There's art, history, and color around every corner. You'll see.

Photo credit: IG: keywestted

Spend one day on the water. Snorkel, visit a sandbar, spend the day at sea, or trade the crowds for the backcountry, kayaking through mangroves and exploring the quieter side of the island.

Or don't make plans at all. Sleep in. Read by the Serenity Pool. Doze off. Wake up and order a cocktail. Sometimes the best day in Key West is the one you never planned.

Photo credit: Ivette León, @ettevi_wanderlust

How do you meet people in Key West (only if you want to)?

You just sit down.

For a little piece of old Key West, head to Schooner Wharf Bar, steps from the resort. Get a seat at the bar and let the conversations unfold. The person next to you has a boat story, the bartender has an opinion about everything, and the band takes requests.

Sunset is the one thing everyone in Key West stops for. Walk the Harborwalk, join the crowd at Mallory Square, get out on the water, or watch it from your balcony. A nightly celebration you don't want to miss. When it's over, you're just a short stroll back to The Marker.

Photo credit: Jim Simmons

The best part of this trip isn't what you checked off a list. It's that every minute was yours. That's the magic of Key West: you come here solo and realize you were never alone. #lovethemarker