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Why we love it: A grande dame of the Gulf Coast with a glamorous history and luxurious amenities to match

The Highlights:
- A spot on the National Register of Historic Places
- Family-friendly amenities like watersport rentals and a kids’ club
- A stunning spa with a rooftop terrace overlooking the beach

The Review:
Known to many as the Pink Palace, The Don CeSar is a beachfront icon. Real estate scion Thomas Rowe built the hotel in 1928 as a tribute to his lost love, turning it into a popular destination for such acclaimed Gatsby era figures as Clarence Darrow and F. Scott Fitzgerald. Following his death in 1940, the U.S. Army purchased the hotel to be used as a hospital and convalescent center for airmen returning from World War II, but let it fall into disrepair after the war. Thanks to locals, The Don was saved from the wrecking ball in 1971, reopened as a full-service resort in 1973, and added to the National Register of Historic Places just a year later.

Today, the hotel continues to preside over the windswept dunes of St. Pete Beach, drawing guests with promises of ocean views and epic sunsets. The setting is so iconic, in fact, that movies like Once Upon a Time in America feature scenes with The Don in the background. The 241 contemporary rooms and 36 suites boast coastal charm, with crisp white linens and louvered windows accented by pops of turquoise and peacock blue. Two outdoor heated pools, a private beach, a game room, and complimentary bicycle rentals keep families entertained, while an 11,000-square-foot spa caters to couples seeking romance. When hunger strikes, guests have their pick of everything from a casual cafe, traditional beach bar, and nostalgia-inducing ice cream parlor, to a poolside grill and award-winning restaurant serving local produce and seafood.

For a truly relaxing vacation, the beachfront Westin Dawn Beach Resort & Spa, St. Maarten features everything you need right onsite: gamble in the casino, swim in the infinity-edge swimming pool, have a drink in the pool bar, dine at one of the three onsite restaurants, indulge with a treatment from their spa, or just enjoy the ocean views from your room. Friendly staff ensure a personalized stay, enhancing the overall experience. The Westin St. Maarten is also an excellent choice for families, as their Westin Kids Club® offers games, activities, crafts, and day trips. Babysitting services are also available. And for those trying to stay healthy while on vacation, the Westin Essence program offers SuperFoodsRx™ meals, a fitness studio, spa, and Westin Heavenly® Beds to help you be kind to your body. Free Wi-Fi is available throughout the property. Maarten.

Day or night, the Lawn is a favorite Canggu hangout. With the grassy expanse and mats to lounge on, a small pool facing the beach, a dining area, and a covered bar, this sunset spot has enough room for everyone. No need to jostle for space. Groups of friends and families enjoy long, lazy brunches, lunches, and dinners, the meals sometimes merging into a fantastically relaxed day. If you’re feeling adventurous, try the Balinese-style babi guling pizzetta, or order a bit of everything from the grazing menu, which offers smaller dishes like crispy lemon squid and fresh rice paper rolls to share. The food is a bit expensive for those traveling on a budget, but the variety of dishes and the fresh ingredients make it splurge-worthy.

Updated in 2017, the rooms and public areas in this attractive, airy resort have an island-themed decor. Rooms now come equipped with marble bathroom vanities, Smart LED Samsung televisions, and Starbucks Coffee. But the star attraction remains a prime, crowd-free position on Grand Cayman’s Seven Mile Beach, famous for clear water and powder-fine white sand. Resort sun loungers are spread far apart to give guests a sense of privacy. A day camp with fun activities and a healthy meals program for kids (ages 4-to-12) means parents get guiltless downtime (or scuba diving and other water sports). Shopping and alternative dining are within walking distance.

This is a peaceful spot to land when you want to soak up the tranquil breezes off the Chesapeake Bay. Head down south and enjoy a quaint stay in this hopeful little town still showing forth the glory of its historic roots. Grab a bicycle from the Hope & Glory Inn’s bike stand and head on over to their namesake vineyard. Taste a few of the delicious wines and dine at the Inn’s restaurant where the grub gives ‘country’ food a new meaning.

The Hoxton is one of Downtown Miami‘s newest hotspots. The bar and restaurant is located in Brickell, usually the home to steakhouses and pub, but the Hoxton is a breath of fresh air. The 2-story bar and restaurant is like a beach house in the middle of a totally urban environment. You don’t even feel like you are in downtown once you enter the outdoor patio. You’ll feel like you are in the Hamptons with a variety of plush couches, mood lighting and soft music. The menu includes several seafood favorites including mussels, oysters and chilled Florida shrimp. The cocktails include fresh fruits, juices and herbs, each filled with the exotic flavors of South Florida. Be sure to stop in for happy hour. There’s music and live entertainment nightly, transforming the restaurant into a hot spot for dancing and jamming.

Travelers seeking spacious accommodations in buzzy South Yarra would be wise to choose this MGallery by Sofitel property on shop-lined Chapel Street. The smallest of its 111 guest rooms start at a roomy 410 square feet and feature plush king beds, black-marble bathrooms, and smart TVs, while its largest split-level suites are nearly quadruple in size—one has its own private spa bath and sauna, while another houses a dining table for 10 and a baby grand piano in the living room. The interiors scream personality, with a bold color palette of hot pink, turquoise, and lime green and decorative elements like gray-and-black leaf decals. After a day spent shopping in the nearby boutiques, unwind in the gym and sauna, then chill out in one of the plush lounge chairs on the seasonal rooftop deck or around the indoor pool, which is covered in a retractable glass roof that opens during warm weather.

One of the most luxurious Western guest ranches, opened in 2005, Paws Up Montana, in Greenough, sprawls over 37,000 acres of classic Montana landscape: elk-filled meadows, rocky peaks, and ponderosa pines in the Blackfoot Valley, with the river of the same name running through it all. The most sought-after accommodations are the “glamping” tents on the banks of the Blackfoot or along Elk Creek that are available May through October and organized into five separate camps, taking just six guests each. The camps combine a Western lifestyle with an African safari formula: canvas suites with private baths, a communal dining pavilion with fireplace and fire pit, private camp chef, and butlers to help organize guest activities. Families and friends who prefer four walls between themselves and nature stay in enormous wood-and-stone villas with heated hardwood floors, fireplaces, leather furniture, huge flat-screen TVs, and panoramic windows; some of these homes come with outdoor hot tubs and tented bedrooms for kids.

All guests have the opportunity to hike, rappel, canoe, play paintball, take cooking classes, and more, but the main action is on-site fly-fishing and horseback riding for all levels on 100 miles of private trails or in a 23,000-square-foot equestrian arena; adults and kids 12 and up can help move small herds of Black Angus cattle on sample stock drives. If parents want private adventure time, kid wranglers entertain young’uns. In the evening, communal entertainment takes place in a renovated barn that serves as stock sales venue, dance floor, and movie theater. Despite the busy activity menu and flow of golf carts transporting guests to and fro, the ranch is large enough, and accommodation so widely spaced that guests can survey the landscape and not see anyone.

Chef Jacques Larson operates on the fringes, creating destination restaurants far off the Charleston peninsula, first with his Johns Island trattoria, Wild Olive, and now with this seafood-and-pizza-focused outpost on Sullivan’s Island. His signature ricotta gnocchi with short-rib ragù and horseradish gremolata sets tastebuds salivating and inspires frequent return drives to the beach, as do pizzas like “Old Danger,” featuring pancetta, black pepper, and a farm egg over melted mozzarella and parmesan. Weekend brunch is in especially high demand, but the well-designed, nautical-but-not-kitsch dining room and wraparound raw bar stay packed for lunch and dinner every day of the week. Downstairs, there’s an in-house coffee-and-gelato shop, BeardCat’s, that doles out breakfast sandwiches and lattes in the morning and 20 flavors of house made icy goodness all afternoon and evening.

The Old Man and the Sea in Savaneta is an ideal place for a romantic island dining experience, amid the ‘clicking palms,’ overlooking the water. Feel the sand beneath your feet, and listen to the waves gently lapping the shoreline as you enjoy a sunset supper in an intimate setting.

The hippest kid on the block has risen from the most unlikely of origins: the Fenway Motor Hotel, a run-down mid-century relic that once housed all manner of misbehaving musicians. Today the hotel feels more like an of-the-moment Los Angeles enclave, with mid-century furnishings, floor-to-ceiling Mondrian stained-glass windows, and upscale bathrooms. Local music and pop-culture memorabilia decorate the rooms and foyers, from framed Boston Phoenix covers (the city’s now-defunct alt-weekly) to vintage speakers and ‘70s-era phones.

In keeping with the rock-and-roll theme, both the lobby and the outdoor pool area regularly host live music. Lansdowne Street, home to legendary clubs like House of Blues, is just steps away, and of course no visit to Boston is complete without a stop at next-door Fenway Park (tours of the ballpark are available daily and year-round).

Set in the Catskills, the Graham & Co is a boutique hotel that has reimagined the classic weekend mountain getaway. Located about two-and-a-half hours from New York City, this retreat offers spacious minimalist rooms, some with kitchenettes. Details include Mexican blankets, Tivoli radios, and custom bath amenities that are available for purchase at the front desk. The Graham & Co is designed as a place to sit back and read while putting your feet up next to the fire pit. Plenty of outdoor activities (fishing, hiking, skiing) are nearby, but many guests settle into the property and its Adirondack chairs, hammocks, and picnic area for a welcome escape from the bustle of city life. Explore the town of Phoenicia on a complimentary bike or simply stay put at this unpretentious mountain property.

Situated on 10 acres in the heart of downtown, this 24-story hotel lives up to its name with 775 elegant guest rooms, appointed with handcrafted cherrywood Richelieu furnishings, floor-to-ceiling windows, Italian marble bathrooms, and spacious balconies. Public outdoor spaces include an immaculately manicured courtyard garden with a central fountain, a pretty-as-can-be terrace café serving house-made breads, and an outsize pool lined with loungers, all against a backdrop of classic white granite. To top it off, the hotel also features a colorful toy store with costumes galore, a jewel box of a sweets shop with macarons and other divine confections, and a men’s haberdashery. The lobby lounge hosts a live jazz band on weekend nights, and the staff tends to a crackling open fire during cool weather.

Kids visiting the Westin will love the resort’s kiddie pool, featuring an enormous waterslide that will make adults envious. There’s also a large indoor-outdoor play area (packed with toys!), mini putting green, and sandbox.

Relaunched in a historic building as a new boutique hotel in summer 2017, the Trafalgar St. James is (as the Brits say) bang in the middle of London, perched on Trafalgar Square. The central location overlooking Nelson’s Column and the National Gallery makes it a draw for sightseeing visitors, while the buzzy rooftop bar and underground lounge are popular meeting spots for locals. Sleep with Mick Jagger (in photo form, framed over the bed) in elegant modern guest rooms with buttery leather headboards that echo the swank booths downstairs in the Trafalgar Dining Rooms. The restaurant serves all day, from cold-pressed morning juices to a post-theatre pulled lamb burger. Make reservations for drinks and nibbles on the Rooftop, and enjoy the views of central London even during cooler months with blankets and outdoor heaters. The hotel taps into local tastemakers and influencers to curate tips and itineraries for guests.