Finding the Soul of Key West

The newly revived La Concha remains a landmark hotel that presides grandly over Duval Street.

Returning to Key West after 25 years, I wasn’t sure what to expect. I had heard stories of endless parties and crowds, and worried that the island’s soul had been replaced by bar crawls and bachelor antics. Personally, I prefer art, history and being out on the water, not foam parties.

But I was pleasantly surprised.

Traveling solo through the Keys, I felt safe and welcomed every step of the way. Key West still holds tight to its artistic roots, storied past and natural beauty — I found the same charm that had captivated me decades ago, only this time with more appreciation for the moments in between.

After a seven-hour drive from Ocala, I arrived ready to check into the freshly restored La Concha Key West, a landmark hotel that first opened its doors in 1926 and still presides grandly over Duval Street. It is part of Marriott’s Autograph Collection. The renovation honors the building’s elegant past — once a glamorous haunt for literary giants like Ernest Hemingway and Tennessee Williams — while updating it for travelers seeking both comfort and character.

But this isn’t just a revival of architecture; it’s also a celebration of taste. Inside the hotel, I discovered the Tropicado Mojito Bar, a new gem in Key West’s culinary scene. There, I met Chef Juan Cuadra, whose enthusiasm for the menu was as palpable as the tang of citrus in the air.

“Our tapas menu offers something you can’t find anywhere else in Key West,” he told me, and I believed him after the first bite of my Catch of the Day Tamal — a blackened local catch served with a delicious sauce over a tamal. Diners at the table next to me ordered the Yuca Frites, which had flat iron steak over fried yuca with key lime chimichurri. The portions were generous – its comfort food elevated to an art form.

The next morning, I woke before the cruise ships arrived and wandered the streets in rare solitude, the quiet punctuated only by the crowing of Key West’s famous wild roosters. I walked through the Truman Annex, a serene neighborhood near the historic Truman Little White House, where leafy trees arched over narrow lanes and pastel cottages.

Later that day, I had a Zen moment at the Key West Butterfly and Nature Conservatory. If you go, sit quietly on a bench. Let the butterflies come to you — one might land gently on your shoulder, as one did with me, as if to say you’re exactly where you need to be.

Within walking distance of the La Concha are a variety of shops that feel more like artist enclaves than tourist stops. Key West Pottery at 1203 Duval Street, run by a couple who embraced the “conch life,” offers handmade ceramics rich with texture and tropical soul. Other standouts included:

Tucker Provisions – 611 Duval Street, curated with taste and quirk
Besame Mucho – 315 Petronia Street, a romantic general store of scents and gifts
Belleane Art – 1201 Duval Street, showcasing striking local paintings and prints

And because Key West always has one more surprise waiting, I attended my first drag show at The Birdcage Cabaret, located a few blocks from the hotel. By fate, I was seated next to Carlos Home, the 2022 Fantasy Fest King. When he heard it was my first show, he summoned the queens, including Christopher Peterson — dazzling in sequins and smiles and tons of grace — for all my newbie questions.

Then, they put on a performance that blew me away.

The queens referred to Carlos as “the King,” which made him giggle.

“I was the king of Fantasy Fest a few years ago,” he explained.

Fantasy Fest is an annual 10-day celebration for adults that has been going on since 1979. The La Concha has one of the best balcony spots to watch the festival parade.

“How do you become King or Queen of Fantasy Fest?” I asked Carlos.

“You raise the most money for charity,” Carlos said with a grin. “That year, we raised over $300,000.”

To date, the festival has raised approximately $5 million to support those diagnosed with HIV.

“But” he added with a giggle, “the reason I was able to raise so much was because of the generosity of my husband. I married well!”

As I walked back to the hotel that evening, I called my best friend, who now lives in Delaware, and told her all about the experience and how generous everyone was. I want to return with friends to this place and this time book one of the Penthouse Concierge Floor suites at La Concha, with sweeping views of the water and Lower Keys and plenty of space for lounging between adventures.

And next time, I will plan to get out on the water with Sebago Watersports, a trusted outfitter that offers everything from snorkeling excursions to sunset sails, according to hotel staff.

From monarchs to hospitable drag queens to mojitos and comfort food with flair, Key West has a magic that comes from its joyful insistence on being itself — eccentric, welcoming and proud of its past.

I’ll be back for more.