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Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

The smallish Plaza Manuel Tolsá—at the end of Calle de Tacuba—is an all-but-perfect urban conglomeration that will thrill architecture fans. To the south lies the 18th-century Palacio de Minería (a former engineering college) whose solid, sober mastery of imposing volume is leavened by the wavy effects of the city’s sinking soils; to the north is the former Palacio de Comunicaciones, now Mexico’s National Art Museum. The collection here is a winner—but some of the structure’s soaring neoclassical spaces will leave you agog. At the corner with the Eje Central thoroughfare stands the city’s beloved old post office, noted for its eclectic, Venetian-style facade and coruscating interiors in marble, bronze, and iron (don’t miss the grand staircase). A recently restored equestrian statue of a somewhat dopey-looking King Charles IV of Spain is a marvelous finishing touch.

Why we love it: An ultra-stylish stay that brings U.K. hospitality to Brooklyn’s most bustling neighborhood

The Highlights:
- Smartly designed rooms that come with neighborhood guides and daily breakfast bags
- An on-trend aesthetic from two U.K. design icons
- Two alfresco dining options

The Review:
The Hoxton has a knack for opening in only the coolest neighborhoods—first in London’s Shoreditch, then in Paris’s 2nd Arrondissement, and now in the hipster haven of Williamsburg, Brooklyn. At the company’s first stateside property, housed in the former Rosenwach Water Tank Company factory, the surrounding area informs much of the aesthetic. The 175 rooms are outfitted with locally made ceramics, bespoke bedding by Dusen Dusen, and books curated by neighbors.

Beyond the Brooklyn details, mid-century-meets-urban vibes prevail, from brass accents and mohair headboards to raw concrete ceilings and subway-tiled showers. It’s a stylish approach from design team Ennismore and Soho House that carries through to the public spaces like Klein’s, the lobby-level restaurant situated in the building’s original brick carriage house that serves American-inspired fare around the clock. When the warmer weather hits, guests can pay a visit to either of the hotel’s two outdoor options. Backyard offers canned beer, classic cocktails, and finger food like Meat Hook sausages, while the rooftop Summerly features lobster rolls, clam chowder, and other East Coast seafood favorites.

From the outside, the Royal Ontario Museum appears to have been struck by a mineral formation from outer space. When the original building was overhauled by starchitect Daniel Libeskind, many locals were dismayed by the new addition, called the Michael Lee-Chin Crystal, but most have come around to its angular charms. Visitors to this museum of world cultures and natural history can work their way through galleries showcasing Chinese sculptures, Canada’s First Nations artifacts and crafts, dinosaur skeletons, and Byzantine artwork. Special exhibits have included everything from the intricate textiles of Mexico to an in-depth look at the culture of tattoos.

Why we love it: A landmark-turned-hotel with elegant decor and top-notch dining

The Highlights:
- Five-star hospitality from one of Europe’s first luxury hotel groups
- Three-Michelin-starred cuisine at 15 Stamford
- An outdoor saltwater relaxation pool

The Review:
Located in Singapore’s civic and cultural district, the Capitol Kempinski Hotel is a modern-day union of two historical landmarks: The Capitol Building and Stamford House. Reimagined by late interior designer Jaya Ibrahim and his team (now part of BLINK Design Group), the property stays true to its roots with a colonial-meets-Art-Deco design, including high corniced ceilings, dramatic archways, and grand windows that reveal sweeping city views. Equally elegant are the 157 guestrooms, which boast Chengal wood flooring, custom lacquered Indian rosewood furniture, and cornices resembled fish scales—a reference to the Merlion, Singapore’s official mascot.

The hotel takes pride in its culinary programming, placing a heavy emphasis on high-quality ingredients and a carefully curated wine selection (reflecting the Kempinski brand’s origins as a 19th-century wine merchant). Nowhere is this more evident than at signature restaurant 15 Stamford, where three-Michelin-starred chef Alvin Leung serves reinterpreted Asian classics like Assam suckling pig with fresh fig and Hokkaido scallops with shiso and soy jelly. For something more casual, sample the specialty rums and chocolates at The Bar at 15 Stamford; take your afternoon tea at The Lobby Lounge; indulge in German breads and pastries at Berthold Delikatessen; or fill up on German-Austrian fare at Frieda. When you need a break from all that eating, pay a visit to the outdoor saltwater pool or spa, where the team performs calming treatments with award-winning products from Gaylia Kristensen.

The Artisan, inside the Stonebridge Inn, serves modern American cuisine, using locally sourced ingredients in a refined and relaxed setting. Sound pretty much the norm? The Artisan is blessed with a charming setting: There’s a lovely stone fireplace in the main dining room and then, up some steps, bar seating and tables in a solarium with mountain views. Outside the solarium, deck seating means dinner with fresh-air mountain views. Set the tone for a great meal by ordering the grilled artichoke heart appetizer, garnished with a truffle aioli and lemon zest. The recommended entree: a New York strip steak, topped with a bourbon, peach, and cherry salsa, and served with cashew rice and scallions.

The Iris Inn, a luxury Shenandoah bed and breakfast, is the perfect base to explore Virginia’s Blue Ridge mountains. Located 30 minutes from Charlottesville, the Inn is close to nearly 30 wineries and is within a few minutes drive to the southern entrance of Shenandoah National Park. Owners Dave and Heidi Lanford warmly welcome visitors to their cozy mountainside inn with gourmet breakfasts and a complimentary nightly happy hour. The eco-friendly B&B also offers an electric vehicle charging station.

Stretching high above Fifth Avenue, the Peninsula is a glamorous, classic hotel. Formerly the Gotham Hotel (built in 1905), this building is at the heart of prestigious Midtown Manhattan with neighbors like the Museum of Modern Art and Rockefeller Center. It has a convenient location for Fifth Avenue shopping and exploring Central Park. The Peninsula is a favorite of New Yorkers for its rooftop bar, Salon de Ning, with its mesmerizing views of the city skyline. Rooms are polished and inviting, designed to resemble a luxurious New York City apartment. Kick off your stay with a classic cocktail in the Gotham Lounge, followed by a locally sourced meal at the elegant Clement Restaurant and Bar.

What was once a pop-up bar, The Broken Shaker is now a permanent fixture at the Freehand Miami. The James Beard Award-nominated bar is located in the high-end hostel on South Beach serving up a selection of handcrafted cocktails. The bar itself is a tiny room by the pool with a 1950s Havana look. You can grab your cocktail—made with elixirs, syrups and infusions using herbs and spices from the onsite garden—and drink it in the bar, or head outside to the pool and nestle into one of the lounge chairs. Away from the hustle and bustle of South Beach, The Broken Shaker offers a more intimate setting than the lavish pools at high-end hotels in the area.

Restored to its former glory in 2008, the Italianate Westin Book Cadillac Detroit in Downtown is on the National Register of Historic Places and has 453 neutral-toned guest rooms—all with city or Detroit River views—an indoor pool, and an award-winning restaurant.

If there were ever a hotel with history, it’s the Singular Patagonia. Opened as a hotel in November 2011, the original building once served as a post-Victorian cold-storage factory built by the British in 1915 for the purpose of processing sheep’s wool and meat to be shipped back to England. Overlooking the waters of Last Hope Sound, the long, red-brick building is located just outside the town of Puerto Natales. After operating for almost 70 years as a factory, it was declared a national historic landmark before being transformed into a luxury hotel.

History is by no means forgotten. The hallways are still stocked with brightly colored machinery—from steam condensers to boilers and forges—all stamped with the name of the British city in which they were built: Derby, Birmingham, London, or Glasgow. Designed by Chilean interior designer Enrique Concha and local architect Pedro Kovacic, the 57 bedrooms stretch along a new wing that was added to the original buildings, and these rooms are furnished with Victorian-inspired furniture.

According to a popular saying in Holland, “Money is earned in Rotterdam, divided in Den Haag and spent in Amsterdam.” To see where financial division happens in the Netherlands, head for the country’s seat of government: The Hague or Den Haag, as the Dutch call it. Den Haag is a cultured city with just under 500,000 people―less edgy than Amsterdam but more sophisticated than Rotterdam. Amsterdam may be the capital of Holland, but you’ll find the Dutch Parliament, Supreme Court and Council of State in Den Haag. In addition to being the seat of government, the Netherlands’ third largest city (after Amsterdam and Rotterdam) also is the locale for 150 international courts, foreign embassies and international organizations. As home to the International Court of Justice and International Criminal Court, it’s among six major cities that hosts the United Nations, along with New York, Vienna, Geneva, Tokyo and Nairobi.

For a New York experience that’s equally extravagant and convenient, visitors should consider a stay at this five-star hotel, located just blocks away from Midtown Manhattan sites like Central Park, the Museum of Modern Art, and Carnegie Hall. Built in 1904 by John Jacob Astor, the Beaux-Arts building houses 239 rooms across 20 floors, plus an incredibly prized means of accessing each one—an original brass-and-marble staircase runs from the lobby level to the 19th floor (a development that cost Astor $1 million of his $5.5 million investment in the hotel). Once guests do land in their rooms, it will be tough to leave thanks to the signature butler service, available 24/7 for any number of requests, from the everyday to the once-in-a-lifetime. One of your asks should most definitely be a reservation at the on-site King Cole Bar, where bartender Fernand Petiot allegedly invented the Bloody Mary in 1934.

Jamaica’s primary public art museum, the largest of its kind in the Caribbean, is a key part of the island’s history. Established in 1979, it houses more than 2,000 pieces ranging from pre-Columbian works to those of contemporary Jamaican artists and also mounts temporary exhibitions on various aspects of Jamaica’s history and culture. The collection continues to expand and now includes videos, graphic designs, and street art. Guided tours are available, and there’s an on-site coffee shop and gift store.

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.