The sun also rises in Key West

Ernest Hemingway knew a good thing when he saw it. Although it took a few centuries for Key West to evolve into America’s southernmost island paradise, the eccentric, cat-loving author set down roots that made it a haven for others who could relate to his quest for artistic freedom and personal expression. Although there is a lovely Lilly Pulitzer boutique and plenty of T-shirt-and-surf shops, independently owned restaurants, jewellery boutiques, retailers, and art galleries underscore there’s no place like Key West—even within the state of Florida.

The hotel landscape is decidedly retro-cool, especially in the island-city’s Old Town, dotted with everything from Victorian–early 20th century bed-and-breakfasts to mid-century hotels enlivened with bright Caribbean hues. In 2024, the Southernmost Beach Resort & Guesthouses reopened, not only updated and refurbished, but reinvented as a cohesive six-acre resort made up of Southernmost on the Beach, Southernmost Hotel, and guest houses La Mer, the Dewey House, the Avalon, and Duval Gardens. While it parallels the eclectic architectural mix of main thoroughfare Duval Street and Old Town, it also provides different room options for girls’ trips, couples’ getaways, multi-generational family groups, sport fishing and sailing enthusiasts, history buffs, and other travellers.

The location is one of the resort’s most advantageous features since Key West’s most essential historic and cultural sites (Key West Butterfly & Nature Conservatory, the Key West Lighthouse Museum, Truman Little White House, and the Mel Fisher Maritime Museum, among them), independently owned retailers, and quirky-but-beloved restaurant institutions are either walking distance, biking distance, or an inexpensive carpool service ride away. The Southernmost’s concierge can also book outdoorsy activities and fishing expeditions—with a dash of historic lore—through Key West Eco Tour and Big Game Fishing that would do Hemingway proud.

Interior design and architecture with location-specific influences also shapes a stay, paying homage to Key West’s historic evolution over the last couple of centuries. Miami-based design firm Big Time Design Studios creates interiors with a well defined sense of place through greens, blues, peach, and soft pink colours that would do Lilly Pulitzer proud. Whether a guest is staying inside a hotel room overlooking one of several pools or a romantic suite with a cute mini-veranda inside the Victorian-era bed-and-breakfast houses, they are steps from the two private beachfronts as well as a now-iconic buoy erected in 1983 informing visitors they are just 90 miles from Cuba. Four bars, two private beaches, pools, and marquée restaurant Southernmost Beach Café add up to a Key West stay that wraps guests in local colour and flavour.

Regardless of whether guests are here on business or pure leisure, Southernmost’s yoga instructors, personal trainers, massage therapists, and æstheticians ready to help them attain their relaxation goals. While the permanent spa location was being completed at the time of writing, the practitioners are on their game and add all kinds of personal touches to an afternoon or day of pampering. They deftly combine the luxe with the local, with Phytomer skin care products and locally made essential oils on display and combined for the body and facial treatments. While French thalassotherapy, hot stone massage, pedicures, manicures, and location-evocative treatments make up the menu, the standouts include the Tropical Retreat, teaming aromatherapy with an essential oil of choice (coconut cream, pina colada, Tahitian vanilla, or Ocean Breeze), a massage focused on the guest’s specific stress-affected areas, and a paraffin wax foot treatment.

A complimentary beachfront breakfast is available to those staying at the guesthouses, while the property’s amenities and welcoming staff make a Key West stay immersive: bike rentals, electric car charging stations, live music performances, a well organized fitness room, two private beach accesses, two private guesthouse pools, and three pool-adjoining patios each outfitted with its own bar.

Under the direction of executive sous-chef Marisol Luna and the culinary team, Southernmost Beach Café scores originality points for dinner menus that converge Cuban, Caribbean, American, and Asian flavour profiles. The line-up of appetizers is particularly adventurous and includes grilled octopus with tarragon purée and soy black pepper, curried cauliflower bites, conch fritters with garlic-saffron aioli, and king trumpet mushrooms with jalapeno, garlic and yuzu. Main courses are more streamlined yet very customizable. Fresh-caught boat-to-table fish can be ordered grilled, panko-crusted–deep-fried, or blackened with a choice of house mango chutney, coconut curry, Key lime beurre blanc, tomato basil, or teriyaki sauces.

As one would expect, signature Key lime margarita and other perennial pool drinks are available at Shores Bar, Pineapple Bar, Southernmost Beach Café, and others around the property. A full roster of resort activities includes cocktail-making and spirits-tasting classes, trivia contests, Havana Nights salsa classes, and live entertainment.

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Above, from top: Quiche lorraine at La Grignote. The iconic Key West buoy, marking 90 miles to Cuba. Key West Butterfly & Nature Conservatory. Ambiance at El Meson de Pepe. First Flight Island Restaurant & Brewery, located where the Pan American airline was founded.

While the property’s food offerings are solid, one cannot get a complete Key West experience without trying some creative restaurants in town. A couple of blocks from the beach along Duval Street, French-inspired café and bakery La Grignote is a resident favourite that personifies Key West’s international appeal. Signature dishes include Four-Day French Toast, Belgian waffles, a panini with house-made shredded chicken pesto salad, croque-monsieurs and mesdames, and a sublime melt-in-your-mouth quiche lorraine. Familiar sandwiches and salads are also crafted with flair.

El Meson de Pepe is revered not only for its Cuban food traditions and heritage but also as an embodiment of the American dream. The recipe for its success includes founder Pepe Diaz’s formative culinary experience in Spain, a run in Miami as a professional chef, and his family-owned grocery store fuelled by his deli sandwiches and Cuban coffee. An eclectic mix of photos, vintage advertisements, and paintings provides a vibrant backdrop that suits timeless dishes such as ropa vieja (marinated shredded beef with red and green peppers, fresh tomatoes, onions, and red wine), lechon asado (Cuban roasted pork marinated in cumin-mojo sauce), and picadillo habanero (ground beef cooked with tomatoes, onions, garlic, bell peppers, cumin, bay leaves, oregano, potatoes, carrots, and raisins).

The building where Pan American Airlines (Pan Am) was founded almost a century ago now houses First Flight Island Restaurant & Brewery, which preserves the airline’s origins and legacy. It was originally established to fly visitors to Havana and later contracted with the United States Postal Service in 1927 to create the Key West, Florida–Havana mail route. Part of the building makes up the Southernmost Brewery in the USA, and serves perennial brews including Sunset Clipper (citrus and coriander) and Capt Maverick IPA. The restaurant side of the establishment offers fish, seafood, steak, and a host of imaginative appetizers.

As it can be argued that legendary author Ernest Hemingway introduced Key West to a wider swath of Americans, a visit to the Hemingway House, the author’s beloved island retreat, is an essential stop. The quaint Victorian house showcases his life history, lush gardens, and beloved polydactyl cats. However, a Hemingway pilgrimage would not be complete without a visit to Papa’s Pilar Distillery. Just as Hemingway chose his words with intention, so do the present-day distillers when creating Papa’s Pilar Rum in Light Rum, Dark Rum, and Sherry Cask Finish Rum. In addition to the classic guided tour and tasting, there are Bottle Your Own, Rum-makers Round Table, and Bottle Package tours. The adjoining Hemingway Social Club serves up 1930s ambiance, handcrafted cocktails, and live music.

Visitors looking to have all of that with a hefty side of Key West folklore, mystery, and history can book an adventure with Amy Andrade, Southernmost’s guest experience director. While she has won raves hosting the resort’s Wednesday trivia nights, describing her as a proud Key West resident with a palpable love for her adopted home town, they barely scratch the surface. Her customizable city tours, with or without spooky ghost stories, can be booked through her Key West Island Tales Tours or Haunted Key West Tours.

Although Key West retail runs the gamut from inexpensive T-shirt shops to high-ticket atocha (shipwreck coin and treasure) jewellery stores and art galleries, there are some hidden treasures with unique finds and owners that offer a story behind everything they sell. On the higher end, Besame Mucho provides a lovely range of clothing and a pretty shopping environment, while Kirby’s Closet is more than just a delightful vintage shop–new merchandise hybrid. The namesake owner is happy to guide a customer towards pieces that truly suit her personal style. Kino Sandals has been an enduring favourite for its affordable, high-quality hand-crafted sandals. Although Mineshaft Jewelry Designs offers popular atocha pieces in gold and silver, the owners also have unique, slightly edgy original designs exclusive to their homey, well organized shop.

‘Key West is like a miniature New York,’ says an enthusiastic Andrade over a customized nighttime tour that covers ghost stories and swashbuckling pirate tales dating as far back as the 16th century, American history highlights, and the Mile 0 marker. ‘We may be a city of only 30,000 people, but our residents and visitors come from all over the world, from other parts of the US, the Caribbean, Europe, and even Asia to be here. We also have our arts scene, eclectic shopping, and a history of hundreds of years.’ •

Elyse Glickman is US west coast editor of Lucire.

Above, from top: The Key West Custom House. Shopping in Key West. Inside Hemingway House. One of the feline residents at Hemingway House.

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