When expatriate novelist Ernest Hemingway arrived in Key West in 1928, his items of business included obtaining a spare apartment with his second wife, making a name for himself in the bars among Duval Street, and finishing the painstaking process of perfecting what would become one of America’s greatest novels, A Farewell to Arms. Perhaps your own aspirations of a stay in Key West may not be as legendary as those of the world-travelled writer, but there’s one thing Hemingway and every potential Key West tourist have in common: a thirst for life and a town that can quench it.
Today, you can explore the treasure of Hemingway’s Key West in the modern luxury that now outlines the city; historical buildings now house sights and sounds of Florida’s present, while new shops and experiences still ring of traditions past.
A relaxing getaway to The Gates Hotel provides for a calming atmosphere to enjoy a weekend, or a couple of weeks in beautiful Key West with all of its new and old world charm.
Located at the point of entry to Key West, The Gates Hotel is a classic take on the unique culture and stunning beauty of the ocean-laced city. The secluded location only adds to the relaxing flair of the hotel, and trolley rides from the hotel are available to take you straight to Duval street and the center of Key West excitement.
Celebrating local art and modern architecture, sophistication finds its way into every square inch of The Gates. The boutique aesthetic of the lobby creates an intimate escape to relax after a day discovering the island. Calming neutral tones and ocean colors captivate guests in a sea of serenity, while modern accents cool off adventures after a long day in the sand and sun. Minimalism is taken to the next level at The Gates as natural elements create a subtle space for guests to escape from the business of daily life, featured in wooden wall design, ethereal flooring, and thoughtful use of graceful hues.
Lazy afternoons in the Florida heat are given an air of elegance at The Gates private pool, an oasis of relaxation not far from the hotel’s dining and drinking options. Take a dip with a drink in hand as quiet hours spent poolside turn into romantic memories of paradise.
Just a few steps takes you to Rum Row, The Gates’ well-stocked bar, where you can sip on tastes of Key West such as a variety of rum-soaked cocktails. Also outside, the Blind Pig offers delicious and healthy options on location in a food truck-style experience. Enjoy cuisine inspired by Key West’s eclectic tastes of Caribbean, Cuban, and Floridian culture in the form of small bites and tapas.
In true Key West fashion, The Gates fills each room with work from award winning photographer Jorge de la Torriente of De La Gallery. His work captures the vibrancy of journeying to new destinations of nature and beauty.
Jorge de la Torriente’s work found in The Gates can be enjoyed at De La Gallery, where modern exposition of color meets timeless island culture. The gallery has become a locally-renowned site on Duval Street. This road is a work of art itself, lined with buildings that could tell as many stories as only Hemingway could write. The Hemingway favorite Sloppy Joe’s Bar may be the most famous location on Duval, but many new eateries have raised the bar in Key West. Nine One Five restaurant and wine bar offers an elegant place to enjoy a glass or bottle of beautiful wine, exciting cocktails and delicious cuisine while taking in the excitement of the island’s late nights.
If you prefer a more Hemingway-esque drink, your Key West adventure must include a stop to the Key West First Legal Rum Distillery and chat with founder/distiller Paul Menta who embodies quintessential Key West. This distillery combines the best flavors to bring thirsty travelers delicious white rums, made with Florida sugar cane and infused with the flavors of coconut, creme brûlée, and key lime. Their specialty rums are distilled six times filtering out fusel oils that result in headaches to ensure that your drinking experience is unlike any other. The distillery’s rum can also be enjoyed right at The Gates Hotel’s Rum Row Bar.
When Hemingway wasn’t busy writing, if rum was in one hand, it was probable that a cigar was in the other. Keep the traditional Key West experience going with a trip to Rodriguez Cigar Factory, where Danny DiFabio, grandson of the late Angel Rodriguez, now heads up the family’s Key West operation, and where his grandmother, Daniela Rodriguez, still hand rolls hundreds of cigars each day. You can get a taste for exceptional hand-rolled cigars made with cured and aged vintage tobacco leaves in the authentic Cuban style. Founded in Key West in 1984, the factory is the oldest operating cigar manufacturer in town, allowing guests to enjoy a variety of cigars in the cigar garden, a picturesque locale for those craving to breathe in a breath of Hemingway’s Key West.
A few puffs of a hand-rolled cigar might get you in the mood for adventure, and Fury Water Adventures offers catamaran tours fit for whatever you fancy. Chill the night away on a sunset tour, or excite your toes with a trip on Fury’s glass bottom boat as marine life swims right below your view.
Perhaps a bit of a closer perspective is what you’re looking for in your ocean adventure. If that’s the case, visit SUP Key West, where you can have an exciting stand up paddleboard tour of the Key West backcountry. Get up close and personal with wildlife as you take a look at tropical fish, sea stars, and jellyfish, as well as different species of aquatic birds. Even learn from the best with customized paddleboard lessons.
For seekers of the time-honored tradition of soaking up the adventurous life, there’s no place on the island quite like COAST. Partnering with The Gates Hotel, COAST offers a blend of land and sea in a variety of activities for Key West enthusiasts, from bike tours to art classes. COAST’s Stock Rock ’N Roll bicycle tours are an authentic way to take in the joys of Key West’s laid-back personality. (Just note: It gets very hot in the summer months, so if you can’t take the heat do it when the weather is cooler!) This tour includes a stop at The Key West Botanical Garden and takes travelers to Stock Island. Art lovers can participate in screen printing classes at the COAST Studio, as well as taking in a look and listen of local artists and musicians.
Founder Billy Kearins created COAST in an effort to live an endless summer, riding the lines between land and sea and work and play. He specializes in design projects, builds skateboards and surfboards, and is the head visionary for the classes, projects, and showcases held at COAST. Keeping the back roads alive with adventure, an afternoon at COAST pairs nicely with lunch at Hogfish Bar & Grill, the perfect place to try fresh seafood with seaside views. This spot is a favorite for locals, with outdoor dining and live music in a casual atmosphere.
This is just the beginning of the seemingly endless dining options of Key West. If you like to start your adventures early, make time to indulge in breakfast at Blue Heaven before your explorations begin. Don’t be fooled by the chicken and cats wandering around or the quirky artwork—this restaurant takes its food very seriously. Breakfast favorites such as Eggs Benedict and Shrimp and Grits combine down-home charm with quality flavor worthy to make Blue Heaven a Key West staple.
Oysters are on the menu at The Half Shell Raw Bar, where you can get a real old-fashioned taste of the Key West life. Enjoy dinner on the docks as you try seafood that has been plated within hours of being caught.
For larger parties, Catered Affairs is a sophisticated choice for simple and delicious dining. If you’d like to call Key West your destination for corporate functions, family gatherings, or weddings, Catered Affairs brings the beauty of the island and high quality service to your event. Executive Chef Lloyd Gould and Catering Coordinator Amy Lay provide you with the Key West flavors and catering needs you need to throw the best party on the island.
After your journey of finding all that Key West has to offer, stop by The Gates’ sister property, 24 North Hotel. Step back in time as you tour this island escape, which is the perfect marriage of Key West and Cuba. It may only be 90 miles away, but 24 North makes the paradise of Cuba seem even closer. Reminisce the days of Hemingway in Key West’s prime as you wander through paradise poolside at 24 North.
From rum and cigars to seafood and the city, there’s an endless bounty for you to discover in Key West. Pack a fedora, take along your loved one, and maybe even a laptop. If we’ve learned anything from Hemingway, there’s much to write about—let alone enjoy—in this Florida getaway town. It’s time for you to experience it yourself.