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Nestled in Maryland’s beautiful Catoctin Mountains and within miles of Camp David, the U.S. presidential retreat, is the oldest family-owned restaurant in the state of Maryland. Since 1929, Wilbur and Mary Freeze with son Jerry at the helm today has hosted Presidents (from Hoover to George W. Bush), cabinet members, world leaders, secret service, media, and press corps. Within the Cozy, the Camp David Museum showcases the history of Camp David through pictures, memorabilia, and gifts. Its neighboring country inn, the original housing of the secret service who protected FDR while in Thurmont, contain charming suites (each with a jacuzzi and gas fireplace), rooms and cottages named after the presidents, dignitaries, and news media agencies who have lodged and dined at the cozy

Sometimes only a sandwich — thick and hearty, piled with meat and cheese and toppings — will do. The Other Coast Cafe won’t blow your mind with some revolutionary take on the sandwich, but what they do, they do well: hot and cold sandwiches, pickles and potato salad, and friendly service. Their house specialty is the Rajun Cajun (cajun turkey, pepper jack cheese, tomato, onion, spicy salsa mayo), and their reuben is also popular, but don’t overlook the daily specials, like the grilled chicken pesto served on a baguette. If you have very specific sandwich needs, you can also custom-build your dreamwich; seitan is on the menu for non-meat-eaters. Oh, and grab a stack of napkins, because these saucy sandwiches can get messy quick.

This brilliant, partially covered amphitheater offers views not only of the stage but of the stunning Sangre de Cristo and Jemez mountain ranges in the distance. The world-renowned opera company presents five works in repertory each summer. Book well in advance, and don’t miss the elegant tailgating in the parking lot (some participants go as far as white table linens and sparkling wine) before the performance. A picnic can be ordered (at least 48 hours in advance) for pick-up two hours before performances, or you can cobble together your own basket of goodies from local restaurants. Tablecloths not included.

A waterfront icon in the spirit of Sydney’s Opera House, the South Boston home of the Institute of Contemporary Art showcases the work of artists like Shepard Fairey, Tara Donovan, and Nan Goldin wrapped in glass and steel and bathed in copious natural light. With gallery and performance spaces boldly thrust above the Seaport District waterfront, the ICA also presents an ongoing calendar of dance, theater, film, and live music; come on Thursday night and admission and guided tours are free. You can drink in the views along with a Harpoon draft or a glass of chardonnay at the Water Cafe—it’s in the lobby, so you don’t need to pay for entrance to the museum to visit.

It’s all about the fruits of the sea at the Old Fisherman, a local favorite in the center of town. Although the decor is nautical and the dishes are named for seafaring icons, the atmosphere isn’t exactly what you’d expect on vacation. No matter, you—and the locals who pack the place at lunchtime—came for the food anyway. Among the must-try dishes are the Charlie Brouns (fried fish roe in garlic sauce), Juan Henriquez (grilled catch of the day in a mango-coconut-wine reduction), and the Jan Semeleer (conch). Pair your order with an ice-cold Balashi (the local beer) or non-alcoholic awa di lamoenchi (house-made lemonade).

You will want reservations to get into this place. The Mission Restaurant and Lounge serves modern Latin cuisine in a fantastic bar restaurant with a wonderful outdoor back patio (seen here). The chef is Matthew Carter, also known for the House and Zinc Bistro. For desserts, order the pumpkin bread pudding with scotch, pepitas, and pomegranate.

Just 10 minutes from downtown Orlando, in village-like Winter Park, the Alfond Inn has a unique legacy: The boutique lodging was created to provide income for scholarship funds at neighboring Rollins College, one of Florida’s oldest liberal arts schools. If helping students isn’t reason enough to book a stay, the hotel offers lots more incentive. A skylit domed atrium in the Spanish colonial–inspired main building draws your eye to a rotating collection of artwork curated by Cornell Fine Arts Museum, and pet-friendly guest rooms are simple and cheerful. While the hotel is not a full-fledged resort, it offers guests plenty of opportunities to linger. Fire pits and rocking chairs are dotted around the property, and shaded areas for loungers enhance the rooftop pool’s already undeniable appeal. Hamilton’s Kitchen restaurant serves modern Southern cuisine paired with wines selected by an award-winning sommelier. And shops, wine bars, and independent boutiques like Rifle Paper Co. line the town’s Park Avenue, a few blocks away. You can also take a pontoon boat tour for views of many of the Mediterranean-style mansions along the waterfront. Perhaps best of all, Disney and Universal theme parks are only a half-hour drive away.

Portland isn’t exactly the kind of city that’s known for being “fancy,” which was why it was so bold for the Starwood Luxury Collection to add a sleek 15th floor to the top of the iconic Meier & Frank department store building downtown—and turn the top nine floors into the swankiest hotel in town. Who would’ve thought that Louis XVI chairs, tufted white leather and teal velvet, crystal chandeliers, and ornate wallpaper would work so well in the city of plaid, beards, and twee bird patterns? In true Field of Dreams fashion, Starwood built it and the travelers came out of the woodwork, hungry for a luxury hotel that embodies the Rose City with everything from environmentally conscious practices and farm-to-table restaurants to an extensive art collection and rooftop honey bee colony. All that’s to say nothing of the private club-like Library, a collaboration with Portland icon Powell’s Books (the world’s largest bookstore) that allows hotel guests to borrow from a curated collection of 3,000 books during their stay. As it turns out, it’s not all that hard to dress Portland to the nines.

The quintessential Florida sunset moment plays out night after night at this waterfront pub and restaurant in Captiva. Open since the 1970s, the British-style spot draws tourists and locals alike with sweeping views of the Gulf of Mexico and more than 16 different beers. To eat, there are seafood classics like clam chowder, fried calamari, and oysters Rockefeller. Go right before sunset and gather with everyone on the sand to catch the elusive green flash before settling in for your meal.

The Torch, also known as the Aspire Tower, at 980 ft, is the tallest structure in Doha. It was built to house the 2006 Asian Games Flame and it holds the record for the tallest and highest-positioned games flame ever. The Tower, located 20 minutes away from the city centers, serves now as a luxury hotel, although calling The Torch Hotel luxurious is a serious understatement. It has 51 floors, 360 views from any of its lounges, the only revolving restaurant in the country, one of the quaintest places for high tea, and to top it all off, hotel guests have access to a cantilevered swimming pool on the 19th floor--not for those afraid of heights--and a red carpet private walkway access to Villaggio Mall and. As beautiful as it is, it’s worth keeping in mind that The Torch Hotel doesn’t serve alcohol.

The limited-edition Nikes and kiosk of independent magazines (Corpus, Out of Order, System) at this brilliantly edited multibrand boutique in the upper Marais recall the city’s renowned concept shop Colette. But its abundant natural light, and market-fresh, Scandinavian-influenced café make it a place of its own. Minimalist, rustic decor and sparsely furnished racks reinforce a feeling of calm. An in-house florist is in the works. 12 Rue Perrée, 33/(0) 1-44-61- 53-60. This appeared in the October 2013 issue.

The Grounds café—run out of a former pie factory in the warehouse district of Alexandria—makes coffee, juices, smoothies, baked goods, and rustic breakfast and lunch dishes with equal care. Order a flat white (a cross between a cappuccino and a latte) or a piccolo (a mini latte)—there’s also a coffee tasting board and a deconstructed iced coffee—to pair with your seasonal porridge or Big Brekkie (spicy chorizo and serrano ham with braised white beans, smoked peppers, halloumi, avocado, poached eggs, and thick slabs of house-baked toast). After brekkie, peek into the roastery and Potting Shed restaurant next door, and admire the enchanting garden and event space, complete with a coffee cart, barbecue joint, plant stall, and petting zoo.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

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.

This hotel is on our list of The 11 Best Hotels in Chicago.

Chicago invented the skyscraper, and some of the world’s most elegant examples define the city’s skyline. You can stay in the coolest one of them all, designed by German American architect Mies van der Rohe and run by Langham Hotels. To access the Langham Chicago’s minimalist-yet-opulent 268 guest rooms (including 48 suites), you must first check in at the second-floor lobby; its ceiling is hung with silver pebbles, its sofas populated by stylish guests, and its David Rockwell–designed Travelle restaurant alive with music and bites by executive chef Damion Henry during coveted afternoon teas.

The former IBM building with a black exoskeleton also houses a Chuan Spa, which specializes in such Eastern therapies as acupuncture, cupping, and gua sha. A 67-foot-long indoor pool and full-service fitness center are available to all guests.

Anyone spending the night in the rooms, with floor-to-ceiling glass windows framing Chicago views, has access to one of the city’s best concierges, who can organize a River North food tour, a Frank Lloyd Wright walking excursion, or a mixology class at Travelle. Don’t leave without taking a photo beside Jaume Plensa’s “Anna” sculpture in the Wacker Street lobby—then walk over to Millennium Park to see his larger works on display.