Southernmost Style


As Key West celebrates its 200th anniversary, the Southernmost Beach Resort invites all those seeking refuge from the last two years to reemerge in style. Having just undergone a $15 million renovation, the six-acre tropical paradise is back and better than ever.

The Florida Keys have always been honorary Caribbean islands that Americans can drive to, and the stress seems to melt away with each passing mile marker toward zero. Arriving on a perfectly sunny afternoon I’m greeted at check-in with a glass of champagne and an array of smiles. For anyone who has yet to experience the southernmost point in the States, the best way to describe the Keys is that they magically blend a laidback Landshark lifestyle with chic and luxurious experiences – all personified by the Southernmost Beach Resort.

I begin with a tour of the property spanning a significant portion of the southernmost tip of the island with its bright blue buildings designed in classic Key West style sitting like dollhouses along the coast. While the resort encompasses nearly 300 guest rooms, the layout of the unique property is deceptively intimate as each building acts as its own entity. With three pools to choose from, each surrounded by lush landscaping and private cabanas, in addition to a tanning pier and two beaches (a rarity on the island), one could spend their entire vacation in this secluded wonderland.

After meeting with the executive team and touring a recently acquired historic bed and breakfast adjacent to the property, I’m treated to an oceanfront dining experience at the resort’s La Mer – Dewey Guesthouse patio. With only a handful of tables, the intimate setting is offered to guests on a limited basis with a specialty menu that changes every month given the ingredients in season. I meet with Chef Alexander who details the four-course menu and wine tasting.

The sun sets, leaving an outdoor chandelier’s light to compete with the moon reflecting off the waves. We begin with a cool beet gazpacho and sauvignon blanc that casts my mood into a proverbial hammock. Next is an heirloom tomato salad with torn burrata and fresh pomegranate paired with a light rosé. A second course of scallops swimming in cauliflower puree and caviar with a glass of chardonnay livens up our conversations, and the following short rib with a pinot noir peaks the night. We end with poached pears, passionfruit sorbet, and a sparkling rosé for good measure.

Passing the pink and purple-lit glowing pool and cresting ocean waves I reach my spacious room. The charming coastal decor and renovated modern amenities make the space a perfect blend of island comfort. A cologne-sized bottle of Hemingway’s Pilar light rum accompanies me out onto the large balcony overlooking the dark ocean. The evening breeze bristles the palm fronds, and eventually an empty glass signals my retirement to the king-sized cloud in the coolness of the room.

The location of the resort is such that it’s secluded enough from the bustling nightlife for a peaceful night’s sleep, yet also close enough to the main drag of Duval Street that a short walk launches one into the fun. Regardless of where you are on the island, the morning stillness will briefly be interrupted by the countless roosters greeting the new day. I walk a block or two down Duval and find as many cute restaurants as there are art galleries. Coffee and crepes at Banana Cafe sound ideal to start the day. The toughest decision one must make in Key West is the battle between sweet or savory. I opt for an ‘inside out’ French Benedict crepe dripping with key lime hollandaise, and a side banana muffin for symmetry’s sake.

Adventure calls on the opposite side of the island, where a five-minute Uber ride drops me at the marina. I board a Fury operated catamaran where the captain tells us that it might be tough to spot dolphins this morning given the windy conditions, but the sun glimmering off the waves as we glide along the coast is all I need to enjoy the day. While the State of Florida boasts the longest tropical coastline in all of America, the turquoise waters off Key West are unrivaled. This far south we have one foot in the Gulf of Mexico, one foot in the Atlantic, with both just a hop away from the Caribbean.

We arrive at our snorkel spot where I slip into fins and slide down the ladder to the welcoming sea. Even with the slightly choppy conditions the visibility is magnificent, and with my first glance below I already spot waving coral and a school of fish dashing below my feet. Snorkeling along the shallow backcountry one never knows what exotic wildlife will put on a show, but each performance is always a treat.

Back on the boat, I dry off in the sun and drift away with a local Cat 5 Key Lime lager. My camera fails to adequately capture the countless shades of aqua shifting under the cloudless sky. We’re not the only ones enjoying the morning as hundreds of sailboats surround the island.

Returning to dry land I stroll down lively Duval Street, from the colorful Sunset Pier to iconic Sloppy Joes, popping into galleries, shops, and tasting Key Lime pie tastings alike. I spend the rest of the afternoon traversing the Southernmost Beach Resort’s three equally stunning yet different pools while keeping my key lime addiction alive with both a key lime margarita and yes, even a key lime colada, swirling bright green and pineapple gold in perfect harmony.

Just in case the weather, waves, and everything key lime isn’t enough to make me forget about the world, I’m treated to a massage at the hotel’s spa midway between the Shores Pool and the beach. With optimal enclosed oceanfront cabanas for spa treatments, one can enjoy the environment in peaceful privacy. The spa’s talented staff massages the salt and stress from my skin until I’m seemingly in a trance, forcing myself to wake up with a dip in the pool.

At the poolside Pineapple Bar, I join one of the many delightful activities: a paint and sip class. With no artistic talent whatsoever, the resort’s resident art instructor, Lance Berry, reminds us of the old Bob Ross adage that there are no mistakes, only happy accidents. After plenty of laughs, mixed acrylics and cocktails, everyone manages to recreate a Key West sunset painting, each as beautiful and different as the real thing.

Tonight, dinner is offsite located at one of the many reimagined historic Victorian homes on Duval, Nine One Five. A modern American menu with internationally inspired influences, this chic coastal restaurant fuses an always-lively atmosphere with fine dining. A perfectly blended espresso martini casts me into the music, followed by a variety of tastes from shishito peppers to artisan cheeses, bacon-wrapped dates, and ahi tuna gravlax. I decide to take a seafood break and go for a deliciously seasoned filet au poivre.  

For many the night is only beginning, but after my day of exploration I drift back to the tranquil resort for a good night’s rest. In the morning, the orchestra of roosters and waves mark another day in the tropics. Beachfront yoga unfolds for those who didn’t stay too late on Duval Street last night. My path, however, leads to Blue Heaven’s brunch – a must for any trip to Key West. What was once a hideaway known only to locals now sports a line of tourists out the door. Truly hidden in plain sight, the mostly outdoor affair is blocked off from the world with towers of tropical trees acting not only as walls but also a thick ceiling over the scattered tables.

If Key West’s roosters were able to declare a city hall, Blue Heaven would be it. Maybe they’re silent partners in the restaurant as they oversee the grounds without question, scurrying amongst their human equals to feed on leftovers as nothing goes to waste. Operated in conjunction between the best chefs and roaming roosters, this is the kind of place that can only exist in the keys. A bloody Mary, lobster and grits, and a side of banana bread are all far too tasty to share with the roosters swaggering by. Afterwards, I attempt to walk off the rich brunch, passing the Hemingway Museum and lighthouse. Every bungalow is cuter than the next, each painted in pastels in an American nod to Caribbean life.

Back at the poolside bar, I take turns between lagers and dipping in the water as another sunny afternoon heats up the party. After a long day of accomplishing nothing but relaxation, I return to the marina and this time board a Sebago catamaran for a sunset champagne cruise.

For a perfect ending to a relaxing visit in the islands, cocktails and appetizers meld with the live music to quickly turn the boat of strangers into a fiesta of friends. Known for its dazzling sunsets, this evening in Key West exceeds its reputation. A few days is never enough time, but upon my return I will most certainly be staying again at the Southernmost Beach Resort, all the while dreaming about my next Key Lime pie.


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