The Flipside – Waterfront resorts across the globe

Located closer to Cuba than to Miami, Key West is Florida’s irreverent southernmost subtropical paradise, a unique culmination of climate, history, natural beauty, cultural diversity, architecture and unabashed romantic appeal. 

“One Human Family” is the official philosophy of the modern island community of Key West—an easy, good-natured motto that is a shining example of the vibrant, diverse community the Florida Keys is host to. At night, streets filled with sidewalk cafes, open-air bars, legendary pubs, and world-class restaurants with island specialties come alive. The island is rich in culture: dramas, musicals and comedies flourish on local stages. In this city of intriguing contrasts, you’ll easily find yourself wanting to let go of mainland worries permanently—as many have already done.

Waldorf Astoria’s Casa Marina

Casa Marina, A Waldorf Astoria Resort, has been a symbol of the grace, charm and tranquility of Old Key West since welcoming its first guests on New Year’s Eve in 1920. Nestled along the southern edge of the island overlooking more than 1,100 feet of beach reserved exclusively for hotel guests, Casa Marina provides an elegant yet refreshingly simple hideaway for travelers. Listed in the National Register for Historic Places, this Key West landmark has attracted generations of business moguls, artists and dignitaries for nearly a century. Discover accommodations that infuse classic luxury and warmth with contemporary flair ranging from $391 to $528 per night. 

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Once simply just a calm fishing village at the very tip of Baja California, Cabo San Lucas has blossomed into one of the world’s most famous spots for grand scenery, celebrity sightings, sunning and snorkeling that’s unparalleled, and of course, lavish parties. Aside from that, Cabo is an enclave of some of Mexico’s most luxurious resorts and a haven for golf lovers. Here you’ll find restaurants serving superb Mexican fare and the freshest seafood—many even allow you to bring in your own catch to throw on the grill for you. Away from the hub, Cabo offers incredible sites, from secluded white-sand beaches to pristine deserts, and even jagged mountains. 

Breathless

Just steps away from the famous Cabo San Lucas nightlife, restaurants and shops rests this chic, modern and hip resort, Breathless. Located on Medano Beach, the safest swimmable beach in Cabo, the resort offers contemporary suites with private furnished balconies and ocean or marina views complemented by the elevated level of an all-inclusive, Unlimited-Luxury® experience. With Unlimited-Luxury®, guests enjoy unlimited top-shelf spirits and gourmet dining, 24-hour room service, daily refreshed mini bar, and much more. For social butterflies, Breathless provides an exclusive party calendar delivering unique weekly events and monthly themes designed to envelop you in the non-stop celebration. From sensuality shows to mega dance parties, the experience is always hot, exciting and vivacious. This fabulous resort offers a range of accommodations ranging from $258 to $646 per night. breathlessresorts.com/cabo-san-lucas

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Alissa Shulman, MD

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