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Fall Travel

In fall, Key West serves up inspiration and rejuvenation — without the crowds

From Hemingway’s haunts to magnificent margaritas, the southern most city of the continental United States is the stuff of inspiration for travelers.

From left: Many visitors get around Key West on mopeds; a signpost at Fort Zachary Taylor Historic State Park; and Key West’s Old Town Trolley.Alamy Stock Photo

There’s an unmistakable feeling one gets after spending a few days in Key West, Florida. Perhaps it is the pace of life in this island city, where chickens roam freely, and where people gather every evening to celebrate the setting of the sun.

Perhaps it has to do with the local cuisine, bountiful with fresh fish and tropical fruit — and, of course, a namesake pie — or the eclectic, welcoming vibe that permeates the street art and the interactions with the locals.

Whatever it is, it all adds up to a feeling of rejuvenation, of freedom. And fall — during a respite between the summer and winter crowds — is the perfect time to make the journey.


This ability to restore may be why Key West has been a stomping ground for literary figures such as Ernest Hemingway, Tennessee Williams, Judy Blume, and Shel Silverstein. For certain, it is why I find myself here with my partner and our 5-year-old son on my most recent trip, once again looking to heal from the grind of life, and perhaps to find some inspiration.

On our first day, we settle into our room at Kimpton Winslow’s Bungalow (kimptonkeywest.com, 305-294-5229; from $237), a couple blocks from busy Duval Street in the historic Old Town neighborhood. I feel any stress begin to melt away as I walk the property’s lush pathways and explore its quiet corners.

Stepping out of the hotel, I remember that the city’s laid-back vibe is symbolized by how people make their way around. Golf carts and mopeds seem to outnumber cars; zipping through the streets with coolers bungeed to the back is integral to life in the Conch Republic. There’s also an initiative called Car-Free Key West, which encourages visitors and locals to commute by bike, bus, and other alternative modes of transportation. The Duval Loop is a free, air-conditioned shuttle that runs continuously from 6 a.m. till midnight, stopping at 18 popular spots around the island. I found the Old Town Trolley to be the most enjoyable, as each driver livens up the ride with their own narration. One-day tickets cost about $45 online for adults, and include unlimited reboarding as well as stops at various attractions.


The Hemingway Home and Museum.Alamy Stock Photo

A 15-minute drive from Old Town is Stock Island, where we catch a glimpse of a true working waterfront and shipyard. Here, you’ll find the Perry Hotel & Marina Key West (perrykeywest.com, 877-496-8712; from $219), which, in addition to being a place to rest your head, hosts yoga classes run by Salute to the Sol studio that will get your day off to a serene start for $20. Staying somewhere else? The Perry offers day passes ($25 for adults; $10 kids) for non-hotel guests to utilize its spacious pools, fitness center, and other amenities. It’s also home to Matt’s Stock Island Kitchen & Bar, where patrons flock for the ice-cold seafood tower appetizer served in a fisherman’s tackle box.

In the afternoon, I head to the Hemingway Home and Museum (hemingwayhome.com, 305-294-1136; cash only), where visitors can walk through the Spanish Colonial that was the writer’s home for a decade. For artistic types, seeing the small, round dining table where Hemingway wrote is the stuff of inspiration.

Others may gravitate toward the museum’s some 60 cats, half of which have six toes. Guests are welcome to pet and photograph them, but holding these critters is a no-no. The story here is that a ship captain from Massachusetts gave Hemingway a six-toed cat in the 1930s (cats are considered good luck to seafaring folk), and, since then, its descendants have watched over the property, drinking water from a margarita glass.


If you leave the museum with books on the mind, head over to Books & Books @ The Studios of Key West (booksandbookskw.com, 305-320-0208), the shop cofounded by Judy Blume. As the story goes, Blume first came to Key West more than 25 years ago to finish her book Summer Sisters and never left.

If you’re exploring the city, you’ll inevitably want a bit of respite from the sun. On this day, we duck into the Moondog Cafe (moondogcafe.com, 305-741-7699) and cool off with a blackberry lemonade and a red sangria, observing what seems to be a crowd of both locals and visitors.

As daylight dwindles, the island’s many eateries beckon. While it’s noted that Hemingway was a regular at Sloppy Joe’s (sloppyjoes.com, 305 294-5717), a well-known bar that holds a Hemingway look-alike contest each July, I am drawn to something more low key. First Flight Island Restaurant & Brewery (firstflightkw.com, 305-293-8484) was home to Pan American World Airways’ first ticket sales in 1927, when the airline flew between Key West and Havana. The outdoor dining area features a canopy of cascading trees, creating an idyllic spot to sample beers brewed on site and feast on the catch of the day, which, on this day, is the delicious strawberry grouper.


Sloppy Joe’s bar.Alamy Stock Photo

The Southernmost Beach Café at the Southernmost Beach Resort (southernmostbeachresort.com, 800-354-4455) is on the quieter end of Key West and just around the corner from the Key West Butterfly and Nature Conservatory (keywestbutterfly.com, 305-296-2988), where we are headed after breakfast. I opt for the avocado toast trio, with a different topping on each piece. A painter’s unfinished canvases are set up near our table, depicting the Keys’ endless turquoise backdrop.

The butterfly conservatory gives beautiful winged creatures a safe place to fly. Colorful birds and a couple of resident flamingos call this home, too. Time and place slip away as I marvel at the sheer number of butterflies and their unpredictable movements.

Because I’m traveling with my son, who rates our trips by the number of swims he takes, we return to Kimpton Winslow’s Bungalow to splash between the three pools on the property. To my surprise, they’re never crowded. One is situated next to a bar that serves small bites and hosts a happy hour from 1 p.m. to 4 p.m.

Despite the heat, I find myself drawn to the simplicity of roaming without an agenda. As a Mainer, I’m struck by the lack of yard space of homes, even as the splashes of bright colors draw you in. Coming from the land of trees and open space, this thought stayed with me until I realized that Key West is one big backyard where everyone is invited to come as they are.


That evening, we head to the Moondog Cafe with the idea of sampling the dessert counter (the gluten-free Key Lime tart is as tasty as it is beautiful). But my partner, who is Moroccan, is intrigued by the Moroccan lamb pizza, so we opt for dinner on the shaded patio. The pizza comes topped with spiced lamb, tahini, tomatoes, tzatziki, and fresh mint. The rest of the menu is a mix of eclectic dishes and flavors, including Thai mussels, cioppino, and roasted chicken vindaloo.

Moondog is a block from Duval Street, which makes for a lively after-dinner stroll. Street vendors come out in droves at this hour, creating a festive atmosphere perfect for people-watching.

A butterfly at the Key West Butterfly and Nature Conservatory.Alamy Stock Photo

No trip to Key West would be complete without exploring its maritime history, and the Key West Shipwreck Museum (keywestshipwreck.com, 305-292-8990) is worth a visit. A 65-foot lookout tower accompanies the museum, and houses a replica of a bell that, in earlier times, would have rung out when someone spotted a shipwreck offshore. The strong currents near Key West challenged even the most skillful captains; shipwrecks were commonplace. Salvaging goods from these wrecks in the 1800s made Key West, at one point, the richest US city per capita.

Lunch on this day is across from the busy marina, at Fisherman’s Cafe (fishermanscafekeywest.com, 305-741-7044). Menu highlights there include sesame guava toast, conch salad, and a blackened shrimp club wrap. The cafe’s original location was a hangout for fishermen; today, the flavors of “Old Key West” remain. After a bite, be sure to follow the boardwalk around the marina, where you may catch a glimpse of tarpon, nurse sharks, or manatees swimming around the moored boats.

Key West’s Sunset Celebration.Alamy Stock Photo

A trip to Fort Zachary Taylor Historic State Park (fortzacharytaylor.com, 305-292-6713) is a perfect way to spend an afternoon for anyone looking to commune with nature. I walk the short, shaded trails of the park and breathe in the air.

Those visiting for the first time may be surprised to learn that public beaches aren’t exactly everywhere, due to a seaweed problem that often makes swimming difficult. Because of the park’s location, it doesn’t see this infestation as much and offers plenty of space to take a dip.

The nearby Truman Waterfront Park is home to the US Coast Guard Cutter Ingham Maritime Museum (uscgcingham.org, 305-395-9554), where visitors can tour the vessel, which was in service from 1936 to 1988, and honor those who served. An on-board bar provides a unique setting to enjoy a beverage. The adjacent park is a family favorite with splash pads, playgrounds, and a weekly farmers market.

In the evening, we head to Mallory Square (mallorysquare.com/sunset-celebration) for the Sunset Celebration, a nightly tradition that has taken place for over 60 years. This area is considered a tourist trap, but I lose myself in the whimsy as a fire juggler riding a unicycle passes by. As the sun goes down, people sit in chairs and turn their attention to the ocean for one last glimpse of daylight.

Every place has a certain je ne sais quoi — whatever that special quality is for Key West, the island is swimming in it. You can see it on the faces of the people as they watch the sun set into the water. It has something to do with a tomorrow full of possibilities, and full of freedom.

Erinne Magee is a Maine-based writer and author of “This Is Camp: Poems and Stories About Maine’s Most Celebrated Getaway.” Send comments to magazine@globe.com.