“Key West is like a miniature New York,” explains Amy Andrade, “Guest Experience Director” at the Southernmost Beach Resort & Guesthouses during a customized nighttime tour that began at a now-iconic buoy erected in 1983 that informs visitors they are just 90 miles from Cuba. Over the course of the tour, she explained through specific landmarks how it was shaped by various groups, from commissioned and respected European explorers to ruthless pirates to a president and an enigmatic author, all looking for a rare treasure in the New World.
“We may be a city of 30,000 people, but our residents and visitors come from all over the world, from other parts of the U.S., the Caribbean, Europe, and even Asia to be here.”
The Southernmost Beach Resort, which straddles the island’s southern shore and the foot of “Old Town” puts guests in the heart of everything that makes Key West what it is. Better still, much of it walking or biking distance from the Southernmost’s lobby. Earlier in 2024, the resort not only unveiled its remodel but also united several existing properties—Southernmost on the Beach and Southernmost Hotel in the USA along with guesthouses La Mer, The Dewey House, The Avalon, and Duval Gardens—that cover nearly six acres. This helps create a cohesive whole with different room options for couples, multi-generational family travel situations, “girl’s trip” groups, sport fishing adventurers, meeting and conference attendees, and couples.
Interior design and architecture with location-specific influences also shape a stay, paying homage to Key West’s historic evolution over the last few centuries. Miami-based design firm Big Time Design Studios used greens, blues, peach, and soft pink to create interiors with a well-defined sense of place, whether the guest is staying inside a hotel room overlooking one of several pools or a romantic suite inside the Victorian-era bed-and-breakfast houses. Four bars, two private beaches, pools, and marquee restaurant Southernmost Beach Café add up to a Key West stay that wraps guests in local color and flavor. A complimentary beachfront breakfast is available to those staying in the guesthouses.
Southernmost’s amenities and concierge services accessible to all guests make a Key West stay immersive. These include 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. The signature Key Lime Margarita and other perennial pool drinks are available at Shores Bar, Pineapple Bar, marquee restaurant Southernmost Beach Cafe, 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.
Thanks to Executive Sous Chef Marisol Luna and the culinary team, Southernmost Beach Cafe scores originality points for dinner menus that converge Cuban, Caribbean, American, and Asian flavor profiles. The lineup of appetizers is particularly adventurous and includes grilled octopus with tarragon puree and soy black pepper, curried cauliflower bites, conch fritters with garlic-saffron aioli, 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.
Four unique meeting/event venues at the resort all boast configurations of tropical surroundings that set a laid-back but sophisticated tone for meetings, conferences, and family events between 25 to 200 people. The guest services team, activity managers, full-service catering, and a dedicated Sales Team can customize décor, high-tech facilities and amenities, and catering to suit the occasion while adding a sense of place to every event. Stretches of Atlantic Ocean beachfront, expansive outdoor venues, and flexible indoor spaces provide numerous options, whether the occasion calls for a sunset cocktail reception, a seminar or meeting shielded from the hot midday sun, or a celebratory awards event.
Air-conditioned rooms ideal for small events include the intimate Tranquility Room, steps from the Tranquility pool, and the beachside South Beach room is ideal for classroom-style meetings, seminars, and small executive conferences. Planners interested in making a splash with a medium-sized crowd of about 50 guests can choose the property’s adaptable 2,488-square feet of outdoor space thanks to six-foot privacy walls, lush tropical foliage, and seats up to 50 guests.
Regardless of whether guests are here on business or pure leisure, the resort’s yoga instructors, personal trainers, massage therapists, and estheticians are ready to help them attain their relaxation goals. While the permanent spa location was being completed at press time, the spa itself was already up and running with Phytomer skin care products and locally-made essential oils. French thalassotherapy, hot stone massage, pedicures, manicures, and location-evocative treatments make up the menu. One of the standouts is 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.
The “Old Town” 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.
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 fueled 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 (PanAm) was founded almost a century ago now houses First Flight Island Restaurant & Brewery ( which preserves the airline’s 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.
The Southernmost’s concierge can also book outdoorsy activities that Ernest Hemingway would be proud of, such as the Key West Eco Tour and Big Game Fishing expeditions offered. A few steps from The Avalon, La Grignote, a French-inspired cafe and bakery, is a resident favorite and another reflection of 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 Madames, and a sublime melt-in-your-mouth Quiche Lorraine. Familiar sandwiches and salads are also crafted with flair.
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 that with a hefty side of Key West folklore, mystery, and history can book an adventure with Amy Andrade. 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 hometown barely scratches 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.
