Just Back From: Key West


Andrew Harper’s CEO, Crista Bailey, recently spent three nights in Key West, the westernmost island in the Florida Keys. Staying at The Gardens Hotel, a quiet 20-room property we’ve recommended since 2017, she found it to be the very definition of a hideaway: a relaxing enclave with lush gardens, a tranquil environment and a definite sense of place. The cottage compound offers rooms within the original house and in freestanding buildings; Crista stayed in Cottage 1 and liked it for its spaciousness both inside and out.

The entrance to Crista's room at The Gardens Hotel in Key West, Florida - Crista Bailey
Crista's bedroom at The Gardens Hotel - Crista Bailey

Overall impressions: This is exactly how a hideaway should feel: While it was walking distance to just about everything in Key West, it felt miles away from the main drag of Duval Street and the crowds of tourists. The tropical grounds included a small pathway, just off the pool, winding through impressive sculptures and plants. Sprinkled amid the flora were turtles, birds, free-roaming cats and even the occasional (very large) iguana. Key West offers unique outdoor adventure options, fantastic sunsets, fresh seafood and several museums that detail the history of this colorful destination.

Good to know: Most everything can be reached via a 15- to 30-minute walk from the hotel. You do not need a car unless you plan to drive to other Keys.

Favorite moment: Three moments, in fact: the sunsets every evening we were there. I’m not sure if it was because we arrived on the longest day of the year, but the sunsets were absolutely breathtaking — gratifying ends to the enjoyable days.

Sailboats at sunset off the coast of Key West
Sailboats at sunset off the coast of Key West - Crista Bailey

You can’t stop thinking about: Our combo snorkeling, kayaking, sunset-sailing adventure and paddling through shallow waters only to surprise a reef shark, which immediately began thrashing its way out to deeper waters. Our sailing group of 20 had the sea to ourselves, except for the wildlife that call it home. We snorkeled through a sponge garden rich with coral, crab, lobster, urchins and multicolored fish, and one of the crew members walked us through a chart and a brief history of the Key West industries reliant upon the surrounding waters.

Favorite meal: The hog snapper at Café Sole. Both the dish and the venue were a top recommendation of The Gardens Hotel.

Favorite museums: I love Ernest Hemingway, and according to The Ernest Hemingway Home and Museum, he lived on Key West for years and wrote 70 percent of his work from here. Between 40 and 50 six-toed cats now reside on the property — some descendants of Hemingway’s original pet, Snow White. The Key West Art & Historical Society is also worth visiting to learn about Key West’s beginnings. On my trip, there was a Guy Harvey exhibit showcasing his illustrative depiction of Hemingway’s “Old Man and the Sea.”  

The historic town center of downtown Key West
The historic town center of downtown Key West - romrodinka/iStock/GettyImages

Where or what to drink: A mojito or rum runner. I’m not normally a rum drinker, but I enjoyed it immensely while temporarily living like a local in Key West.

Neighborhood to explore: The streets around the hotel showcase some beautiful homes. I recommend going for a walk or renting bikes earlier in the day before the sun shines too brightly and the heat becomes heavy and unbearably sticky. Great walking streets off the beaten path: Simonton, Elizabeth, Petronia.

Surprising fact: Chickens roam free in Key West. I was especially surprised to come across a mother hen and her four chicks crossing the street — in a crosswalk!

A rooster roaming the streets
A rooster roaming the streets - Crista Bailey

Brought back: The Panama Jack hat I acquired on Duval Street to take on my sailing excursion for some sun relief. I’ve worn it since and receive compliments every time I do.

What to pack: Bathing suits, light and casual attire for warm, humid and sticky weather, hats, solid walking shoes, an open mind.

Insider tip: The secret-ish Sunset Tiki Bar at The Galleon hotel — nothing fancy but reminiscent of a scene from a Jimmy Buffett song and not too crowded.

By Hideaway Report Staff

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