Key West for the Solo Traveler

The best trip you’ll take this year might be the one nobody else is invited to.

Morning arrives quietly at Southernmost Beach Resort. The light comes first, rising out of the Atlantic and spilling across the sand. You’re on the porch with your coffee, and it finds you there. No alarm, no itinerary, just the sun keeping its old appointment with the ocean, and you, keeping it too.

Me, myself and Key West. It turns out that’s plenty.

Is Key West good for solo travel?

Of course it is. The island is small enough to walk, surrounded by water in every direction, and friendly in the easy way of places where nobody is in a hurry. For a hundred years, writers, artists and free spirits have come here on their own terms, and so many stayed that staying is practically a local tradition.

Where Duval Street meets the Atlantic, the island slows down. Quiet mornings. A sunrise you can watch from the sand in front of your resort. The livelier Key West waits a few blocks away whenever you’re ready. Perhaps you won’t be. That’s allowed.

Do everything, or nothing at all

That’s the philosophy at Southernmost Beach Resort, and it was made for a trip like this because the whole menu is steps from your room and every item on it welcomes a party of one.

The everything: the lineup changes with the seasons, but expect things like yoga on the sand, cocktail-making classes, steel drums by the pool, games on the deck, a walking club that strolls Duval, and pop-ups you’ll only hear about once you’re here. Check the activities schedule when you’re planning, then show up for all of it, or wave at it from your hammock.

Photo credit: @curatorhotelsresorts 

The nothing: three pools, including our adults-only Tranquility Pool, two beaches, a lounge chair or cabana by the pool or the sand, and a hammock in the sea breeze, made for the days when you just want to be.

And the in-between, which might be the best category: a beachside massage while the Atlantic keeps time. Breakfast by the ocean because nobody’s waiting. Then put the phone down. Pick up a journal and put pen to paper. Let the island give you something to write about.

There’s a reason writers and storytellers have long been drawn to Key West. Ernest Hemingway and Tennessee Williams (and so many others) made it part of their legacy. Today, Judy Blume and Meg Cabot call the island home, while Jimmy Buffett turned its spirit into songs loved around the world. Maybe you won’t write the next great novel or song, but you just might fill a few pages of your own.

Then there’s the porch at The Avalon Guesthouse on Duval Street. Choose a rocker, settle in with a coffee from The Parlour, and stay as long as you like. On Sundays and Mondays, the porch hosts “Quiet Hours – Enjoy a Book!” Pull a novel from the little free library, order something cold, and let Key West slow down around you. From your front-row seat on Duval, watch the island stroll by or get lost in your own thoughts.

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

Whatever the day suggests, and the island starts suggesting the moment you step off the property.

The Southernmost Point Buoy stands a few steps away, so go early before the line forms and get the photo that says, “I was here.” The Key West Butterfly & Nature Conservatory fills a glass dome with hundreds of butterflies drifting wherever they please. On Whitehead Street, visit the home of Ernest Hemingway and the famous six-toed cats that still roam the grounds, and across the street, the Key West Lighthouse & Keeper’s Quarters rewards the climb with a panoramic 360-degree view of the island.

Or rent a bike and discover Key West your way. Pedal Duval, then turn wherever something catches your eye. Browse the boutiques. Stop for a coffee. Wander past gingerbread porches, white picket fences, gardens you can smell before you see them, and the occasional rooster crossing the street like it owns the place.

Photo credit: @keywestted

Or spend the day on the water. Snorkel North America’s only living coral barrier reef, paddle through the mangroves, relax on a sandbar, or set sail on a sunset cruise.

Photo credit: Fury Water Adventures

Where should you eat when the table is all yours?

Some days, breakfast by the ocean is all the plan you need. Come back after a swim. Return again for dinner as the sky changes over the Atlantic. Southernmost Beach Cafe is right outside, so there’s never a reason to rush.

There are so many wonderful restaurants and bars to choose from, and the island delivers: a small, intimate Italian restaurant one night, a food truck and a cold beer the next, raw bars by the Seaport, Cuban favorites, waterfront tables, and some of Key West’s beloved dive bars. You’re never more than a short walk from it all. 

Pull up a seat at the bar or grab a table for one. Before long, conversations unfold with the bartender, the person next to you, or a local happy to share a favorite beach, restaurant, or Key West story. That’s part of the island’s charm.

Memories of Me Time

Watching the light come up over the water.

A slow morning with nowhere to be.

A massage on the beach while the Atlantic keeps time.

Somewhere on the first day, you’ll catch yourself thinking: I needed this.

And somewhere on the last one: If only I had one more day.

Photo credit: Nick Doll

Stay a little longer: the boutique guest house experience was made for exactly this kind of trip, small, personal, and entirely for you. Book your solo stay at Southernmost Beach Resort. #somolife