By Sascha Zuger

Searching for just the right fit for your next stylish escape? Prepare for takeoff from one runway to prepare for walking down another on these fabulous fashion-minded getaways.

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Round Hill Hotel and Villas, Jamaica
Once the private retreat of style icons Jackie Kennedy, Fred Astaire, Noel Coward, Babe Paley, Cole Porter and Grace Kelly, this 27 private villa, 36-room oceanfront room property has long ties with the fashionable set. Excellence awards have flowed to the property in a steady stream, not only for the stylish décor, but for the impeccable service and lush surroundings. Occasional resident and long-time shareholder of the property, Ralph Lauren, consulted on the design for the Pineapple House Guest Rooms, Spa, cocktail bar and newly renovated farm-to-table Grill restaurant. The famous designer finds his serenity on the property, in one of two gorgeous private homes – one atop the hill, the other oceanside.  Apparently, current style-makers are in harmony with his vision. Anna Wintour, Michael Kors, Nicole Miller, Russell Simmons and Tommy Hilfiger have been notable recent guests to the Montego Bay resort. Roundhill.com

Capella Washington, D.C.
Capella’s Resident Stylist (and fashion-guru) April Yvonne ensures guests are dressed to impress with five different packages designed for the designer-savvy. After-hours private shopping with boutique owner meet-and-greets; access to Yvonne’s private room at the Saks Fifth Avenue Club in D.C. and couture labels like Christian Dior, Burberry and more; hand-selected items for your personal taste from the latest lines and fashionable accessories for the new season presented at the hotel while you enjoy champagne and light bites; even a personal perusal of your existing wardrobe to create the perfect look for a night on the town can be arranged. Show off that hot new haute look over a handcrafted cocktail at the hotel’s exclusive rooftop terrace lounge, featuring sweeping views of Washington, D.C.’s iconic landmarks (and an indoor/outdoor infinity pool). CapellaHotels.com/WashingtonDC/

W Retreat and Spa, Vieques Island
Sometimes it’s both the journey and the destination. Arriving to Vieques on one of the tiny nine-seater Cape Air prop planes (one passenger even takes the co-pilot seat) creates the otherworldly ambiance for the whole trip. W guests stroll across the tarmac, after retrieving purses and small hand luggage from a compartment in the wing, to a private lounge where chilled fresh tropical drinks await to refortify as you swap impressions with your plane-mates of the breathtakingly scenic ride over. (And the mutual expectation of hearing, “De plane! De plane!” upon landing). 

Vieques is truly unique, and the fashionable touches and artistry of the soaring W Retreat lobby is a perfect welcome to a place where wild horses outnumber islanders and placidly roam the beaches and perfectly manicured grounds and gardens, munching mangoes. The tranquil, natural spa-style, with occasional bursts of perfectly placed color, continues past the firepit and white semi-submerged loungers in the multi-level pool to the high-ceilinged expansive balcony suites overlooking the turquoise and rich blue sea. The sense of utter relaxation from being in one of the last undeveloped places in the Caribbean pervades the stay, though occasional adventures off property to try out local eateries and visit nearby sea turtle snorkel spots are made easier by onsite jeep rentals. Though full moons are magical, more memorable would be to book during little-to-no moon nights for a visit under a sea of stars to kayak the glowing waters of the island’s Bioluminescent Bay. WVieques.com

The Liberty, Boston
Liberty Boston Hotel has always had a style of its own, as a renovated prison whose cells now sleep trendy guests of a far different stripe than it once housed. The former Charles Street Jail keeps more than a few nods to its roots, with bar and restaurants “clink,” “alibi,” “the yard” and guest-only “catwalk.” The hotel’s “Fashionably Late Thursdays” offers a weekly rotating lineup of local designers (with a few national brands sprinkled in) showing off their hottest new creations on the hotel’s interior catwalks for the pulsing club crowd below. Strolling through the Beacon Hill neighborhood makes a great escape, with panoramic views of the city and Charles River below an unexpected feature (considering the building’s past life!). LibertyHotel.com 

San Juan Water Beach Club Hotel, Puerto Rico 
One of the most stylish spots in San Juan, the common areas of this beachfront Isla Verde property are anything but common. From the waterfall inside the elevator to the shimmering liquid light art in the restaurant, a serious cool factor exudes throughout the public places (and we’re not talking about the complimentary chef-prepared frozen coconut “limber” popsicles hand-delivered to beachgoers). Mist, the rooftop cocktail bar, is the place to don a little black dress under the stars, or just very little if hitting the skyline plunge pool to catch some rays or lounging on a nearby daybed to sip your white sangria at sunset.

One of the biggest treats is the fabulous restaurant, Zest.  Genius chef, Raul Correa, earned the notice of Food and Wine for his modern take on Puerto Rican cuisine with a dash of molecular gastronomy. His Popcorn Soup is an unforgettable starter to an equally memorable meal as artistically inspired as it is delicious. Each dish has a story, many told by the chef himself who frequently enters the dining room to chat with guests and explain how best to get the full sensory experience of the dish (the spoon served with the popcorn soup bears a tiny clip mid-handle that holds rosemary, imbuing every sip with the scent). Service throughout the property is attentive and far friendlier than the uber-hip vibe might otherwise suggest, making this stylish boutique hotel a great fit for fashionable travelers. WaterBeachHotel.com

Rosewood Tucker’s Point, Bermuda
Family-minded fashionistas can share the limelight at Rosewood Tucker’s Point. It’s rare for men to lead the charge in signature local looks, but the long, tailored Bermuda short is world famous and omnipresent throughout the island’s male business community, paired with knee length socks as well as shirt, blazer and tie. These are also considered appropriate wear for Tucker’s Point Golf Club, as well as the Tennis and Beach Club. If women feel too left out, Giorgio Armani’s 2012/2013 Fall/Winter Ready-to-Wear line did feature the long fitted shorts on nearly every model! Show off the island style at Sur Mer, the resort’s beachfront restaurant and bar mixing Provencal French style with fresh seafood, though skip the shorts at the more formal “The Point” featuring PanAm’s unique Sky Club murals.

Looking the best in whatever fashion you choose starts with great skin. Fortunately, Sense Spa offers treatments for the whole family. Signature treatments include spa garden walks to clip body wrap herbs or aloe for massage, a Tropical Rain Splash session in the spa’s 18-head Silver TAG® massage shower, or a sea salt and algae scrub. Teens can choose from ‘Bermuda Lily” treatments offering beauty tips and techniques during a light make-up application and hair styling or a facial with skincare advice. Tweens might opt for a mani-pedi or scalp and foot massage. (Younger children will probably prefer to check RoseBuds for Children’s kids’ camp tennis lessons, golf clinics and cooking lessons at Sul Verde, an onsite Italian eatery.) RosewoodHotels.com/en/TuckersPoint/ 

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