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Charleston’s four-block City Market is a historic landmark (one of the oldest in the country, rivaled only by Baltimore’s Lexington Market) and an essential stop for locally made souvenirs and snacks. Pack up your sweetgrass basket (a traditional Gullah handicraft) and check in for the night across the street at the Market Pavilion Hotel. The hotel has all the plush trappings—Italian marble bathrooms, Hermes toiletries, treats at turndown—one could ask for in the French Quarter, topped off by a rooftop bar and pool with enviable views of the harbor and bustling East Bay street. On a particularly hot Southern night, you might cool off with a nitrogen-infused cocktail before sitting down to a steak dinner at Grill 225, which serves only aged, USDA-Prime meat. The hotel is a member of the Leading Hotels of the World and the restaurant is one of a dozen Great Steakhouses of North America.

Renowned Costa Rican architect Ronald Zürcher looked to his country’s colonial past when designing this hacienda-style property—witness its central courtyard, arched doorways, and terra-cotta roofs. Set amid a 30-acre coffee plantation just outside the capital city of San Jose, the hotel’s 308 traditional accommodations follow suit with dark wood furnishings, but a modern aesthetic pervades renovated guest rooms with streamlined furniture, intricately patterned bathroom tiles, and expansive views that extend from green lawns to forested mountains and urban skyline; some include small balconies that overlook the hotel’s two pools. On-site dining options include gourmet takes on Costa Rican fare at Hacienda Kitchen, Peruvian specialties at La Isabela, and fresh-made sushi at La Castilla, as well as a sports bar and café. The open-air great room invites reading and quiet conversations, but if you’re up for something a little more energetic, there are tennis courts, a driving range, a fitness center, and invigorating coffee scrubs at the spa.

It can be a delicate balancing act, offering the luxury that adults expect of a five-star property while keeping kids entertained and happy. But Le Bonne Entente, sited on a former 120-acre estate about seven miles southwest of Old Québec, hits all of the sweet spots that families look for. Nearly a third of its 160 rooms are suites, making them great choices for families who want a little extra room or privacy. On the grounds, surrounded by well-tended gardens, the seasonal swimming pool is a popular hangout on warm summer days (the hot tub is open year-round). In a lovely court beyond the pool, several unique triple-hammock structures are a perfect place to retreat for some outdoor peace and quiet. Guests have exclusive use of La Tempête Golf Club, as well as a Fun Club for kids up to age 18, providing a home theater, video games, and even a special rest area with beds so parents can sneak away to enjoy a late dinner at MC Lounge, the hotel’s cozy steakhouse.

A must-stop on the traditional handicraft circuit, this massive market—stretching four city blocks in Miraflores!—is home to stall after stall of kitschy bric-a-brac, pre-Columbian–style pottery, alpaca everything and an endless array of Andes-inspired arts and crafts. Come and shop around.

The 112-room Surfjack Hotel channels 1960’s Hawaii, with vintage upholstery on the headboards, reed ceilings, and midcentury modern furnishings. The onsite Swim Club, with its outdoor pool bar, hosts music events and movie nights. Don’t miss a meal at Mahina & Sun from celebrated Honolulu-born chef Ed Kenney, whose menu showcases island cuisine and ingredients, or a trip to the Olive & Oliver boutique, whose clothing and accessories line are inspired by Hawaiian culture.

What if you could spend the night in the middle of hundreds of acres of wild scrubland—where large herds of elephant graze, gazelles bound, and elusive leopards patrol—with nothing between you and the canopy of stars but a thin black mosquito net? The Star Beds at Loisaba Conservancy in northern Kenya offer a quirky and spectacular place to wonder at the universe all night long. The camp’s comfortable beds are rolled out onto a private open deck in the evening, allowing guests to watch the darkness set in and the glittering wonder of the galaxy awaken overhead.

So where are we now? Could this be Vienna in central Europe in the early 20th century? Or maybe Paris in the same era? No, this is a small Gothenburg hotel, restaurant, and bar that fulfills the dreams of owner Thomas Peterson. Coming from a well-renowned family in the restaurant business, Peterson wanted to create his personal vision of an extraordinary restaurant and hotel that paid homage to childhood memories of his grandfather hosting celebrities and artists at home and in his restaurant. Try the afternoon tea, or have a drink on the roof terrace. No matter what you eat or drink, the ambiance is a large part of the experience.

Perched 300 feet above the Pacific on 15 verdant acres, Hotel Wailea is a former members’ club that still feels like a hidden enclave of cool. In 2014, new owners invested $15 million in a redesign that left 72 one-bedroom suites with white oak floors, Sub-Zero appliances, and Hawaii-inspired art. Still, it’s the pool that really wins over guests—it’s calm and quiet (thanks to the hotel’s no-kids policy); there are umbrella-shaded loungers and bungalows with fans for when you’ve had too much sun; and the beyond-gracious staff are always at the ready with water, cocktails, kombucha, and coconut water. The hotel lounge offers free wine and appetizers at 5 p.m. on Friday nights, while the farm-to-fork restaurant highlights produce grown in the resort’s own garden. Complimentary on-site activities include yoga, outrigger canoeing, and mixology classes, but guests can take the hotel’s Tesla Model X house vehicles anywhere in Wailea or rent an electric bike and cruise the South Maui coast if they want to get off property.

A collection of rambling beach bars, The Strip on South Frigate Bay is the best “lime” on St. Kitts—a beach bash by day that transitions to an open-air dance party, moveable feast, and pub crawl by night. The area is within walking distance of the St. Kitts Marriott Resort, but it’s a popular nightlife destination for locals and visitors from all over the island. Don’t miss Mr. X’s Shiggidy Shack, the most famous bar on St. Kitts, where you can enjoy grilled lobster alongside an ever-changing lineup of live entertainment, from karaoke to fire-eaters. Also worth visiting are Vibes (St. Kitts’ closest thing to a sports bar), ChinChillas (for Mexican food), and The Dock Bar, which offers a more relaxed scene and, as its name suggests, its very own dock. Wherever you land, expect live bands and DJs to keep the dance floor hopping well into the wee hours. If you get tired, cool off and then rev up with a “Ting with a Sting,” a popular drink of local CSR rum mixed with grapefruit soda.

The Four Seasons Hotel Buenos Aires, which opened in 1992, is really two hotels in one. The more historic of the two is the three-story, Belle Epoque mansion, built in 1920 as a wedding gift from Félix de Álzaga Unzué, a member of a prominent local family, for his bride, Elena Peña. There are mansard ceilings and toile de Jouy wall panels, and many suites are housed here. The other building is a modern 12-floor tower, which holds the bulk of the rooms. These feature double-glass windows, private bars, and armoires with HD TVs. Every cushy amenity expected of a Four Seasons property is found in both styles.

In 2013, most of the common spaces underwent a $49 million renovation, completely overhauling the lobby and the spa, and adding two new restaurants. There’s still the Roman-style outdoor heated pool overlooking La Mansión, but to complement it, more of the outdoors has been worked into the hotel: lavishly landscaped gardens, a rooftop garden, and a glass-enclosed asado-style restaurant that can be opened up to fresh air.

Originally built as luxury apartments near the Tivoli Gardens and City Hall, in central Copenhagen, the historic building now housing Hotel Alexandra has been a hotel since early 1890. After World War II, when it became the Hotel Alexandra, each of the rooms was painstakingly reimagined using exclusively Danish mid-century modern design, from the colors and fabrics to the furniture and art. Stepping into the lobby feels like stepping back in time to the Copenhagen of the 1950s and ‘60s, when the designers whose work fills the hotel were in the prime of their careers. Taking this dedication to Danish design a step further, each of the 59 rooms and suites has been decorated with vintage furniture and wallpaper from the ‘50s and ‘60s including works from some of the most famous Danish designers of the era: Finn Juhl, Verner Panton, Hans J. Wegner, Nanna Ditzel, or Arne Jacobsen.

But the hotel doesn’t live only in the past. Its dedication to environmental responsibility is evident throughout, and nowhere more so than in its environmental certification from Green Key, a laudable feat even in eco-conscious Denmark.

Two blocks from Union Square, Hotel Adagio is a stylish retreat from the frenetic energy of downtown San Francisco. Built in 1927, the Spanish colonial revival building has a stunning cream facade with intricately carved arches that surround the entrance and windows. The interior also retains many of its original features, including rope crown molding and the top floor’s hand-painted ceilings. Conference-goers and event attendees will be impressed with the hotel venues’ city views, elaborate woodwork, and high ceilings.

Hotel Adagio is part of the Marriott’s Autograph Collection, and the recently renovated rooms are appropriately named Audition, Act One, Encore, Applause, and Actor’s Studio. The decor uses a contemporary palette that mixes warm burgundy and chocolate hues with lime green and white. Get ready for a night out as you jam to your own music, thanks to each room’s iHome docking station. Then, head down to the hotel bar, the Mortimer, to start the evening with a craft cocktail.

If a hotel has a swank spa that administers treatments using ultra-expensive (and effective) Sisley products, it’s probably something special. And if those treatments come in a Victorian manse overlooking the placid waters of Kenmare Bay in Southwestern Ireland’s Ring of Kerry, it’s yet more likely to engage even the jaded traveler’s predilections for plush resorts. Kenmare Manor, a turn-of-the-19th-century stone building backed by patchwork hills and forests, looks like something out of a storybook. But it’s more than attractive: At SÁMAS spa, the treatments, which are indeed high-caliber, come with views of the misty woods (from the pool) and the bay and mountains (from the relaxation room). Staff are attentive to even tiny details, like buttery Irish shortbread at turndown. Breakfasts of smoked salmon and eggs and flaky scones are served by smartly dressed waiters rather than set out at a buffet. The hotel’s restaurant is known as one of the best in the country for wild-mushroom risotto and Kerry lamb loin with eucalyptus-flavored peas.

The Post Hotel & Spa is set in the heart of the pristine Banff National Park, surrounded by the Canadian Rocky Mountains and overlooking Lake Louise. The original log-walled lodge—opened in 1942 as the Lake Louise Ski Lodge—has stone fireplaces and a cheery red alpine roof, and the numerous add-ons, extensions, and renovations over the years have preserved and accentuated this rustic design. This is further enhanced by the hotel’s interior color palette of burgundy and neutrals, and set off by luxurious touches such as overstuffed couches and Egyptian-cotton sheets. The accommodations include intimate cabins for two and a 3,000-square-foot mountain chalet ideal for groups and families. Just minutes away from one of Canada’s largest ski areas and blessed with an abundance of perfect powder each season, the Post Hotel & Spa is popular with skiers and boarders from across North America; in summer it attracts outdoor enthusiasts keen to explore the myriad treasures of the national park. It has been a Relais & Châteaux property since 1990.

On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.