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Since opening in 1819, Australia’s first barracks has housed British convicts, female immigrants, destitute elderly women, courtrooms, and government offices until it was finally declared a museum in 1979. During a twice-daily tour, or with the help of an audio guide, visitors get a glimpse of how high-skill prisoners lived, worked, and slept (on hammocks) during the 19th century—often freely working in the city by day but sleeping alongside more than 1,000 thieves, conspirators, bank robbers, pirates, and bushrangers by night. Offered in the original convict bakehouse and store, a house-made pot pie, burger, or cake with a schooner of beer at Bakehouse is a welcome end to the experience. Outside, freedom has never felt so good.

An hour’s cross-island drive takes you to Kalinago Territory, officially established in 1903 as the Caribbean’s only autonomous enclave for indigenous people. The settlement covers six square miles, and many of its 3,000 inhabitants live in traditional wooden huts. Guests are welcome at a model village, where they can watch dance performances and shop for reed baskets and other crafts.

Halifax’s identity is tied to the sea, and its rich maritime history is the central theme of this eclectic museum. Popular exhibits include one dedicated to the role of Halifax after the sinking of the Titanic (the city’s ships helped with the recovery) and the devastating Halifax Explosion, a 1917 ship collision that killed 2,000. Don’t miss touring the CSS Acadia, a naval vessel once used for hydrographic missions.

Carey Bringle hails from West Tennessee and grew up around serious barbecue culture. A photo on the wall of Peg Leg Porker, depicting his grandfather cooking hogs in the South Pacific during World War II, attests to that. It’s still a family affair at this Gulch restaurant: Bringle’s wife and kids work with him in the kitchen, dining room, and business office. The white box of a building on the edge of the Gulch has a no-frills, classic barbecue joint decor. Aside from family photos on the walls, the focus here is on the food—dry-rub ribs, pulled pork, and smoked chicken with sides like smoked green beans, slaw, potato salad, and mac and cheese.

Set on the northern shore of Lake Union—a body of water the size of Monaco—this rustic-chic, nautical-themed restaurant offers dazzling views of the Space Needle and downtown skyline. Its menu blends Mediterranean flavors with local bounty: Expect highlights like grilled octopus with taramasalata, charred carrots with cocoa, and a salmon gravlax tartine with za’atar, green apple, and cauliflower labneh. Finish with a rhubarb-pistachio cheesecake or a cheese from Vashon Island’s Kurtwood Farms. For extra Northwest credit, arrive in a kayak or on a stand-up paddleboard, or rent a ride from the Center for Wooden Boats (cwb.org)—then moor near the waterside fire pit!

If visiting a miniature version of a country the size of a postage stamp makes no sense to you, stay away from Madurodam, a top tourist attraction in Den Haag featuring historic Dutch towns, ports, canals, roads and monuments re-created on a 1/25 scale. On the other hand, if you fancy learning about the history of a nation that would be underwater were it not for Dutch ingenuity, by all means visit this interactive park that tells the story behind the battle against water, as well as many historic venues that still exist in Holland today.

Surrounded by bold artwork inside and magnificent ocean views outside, guests are never quite sure where to direct their gaze when they arrive at Ellerman House. A stay here is a bit like visiting an elegant and attentive friend, starting with the complimentary airport pickup straight through all the thoughtful, personalized touches (guests might find a bottle of their favorite vodka already stocked in their room). The hotel owner is a well-known aficionado of South African art, and his private collection graces the walls of the guestrooms and public spaces. True art fans should be sure to visit the on-site gallery to view masterpieces by Louis Maqhubela, Wayne Barker, and Angus Taylor. If it’s not occupied, also sneak a peek at the breathtaking wine gallery, which features a wall made of soil from the Cape Winelands and a spiral-shaped wine rack modeled after a corkscrew.

Sitting on the edge of a cliff, this luxuriously appointed hotel makes for one of the best spots in Cape Town for a sundowner. Have a cocktail on the terrace while watching the fiery African sun meet the tumultuous Atlantic waves.

Long considered one of the top hotels on Oahu, the Kahala has always been a particular favorite among the type of guests who travel with their own security detail. A number of past U.S. presidents, plus kings, queens, princesses Grace and Di, a handful of Nobel Peace Prize winners, rock stars, and movie stars, all have slept under its venerable roof at some point during the hotel’s 50-year history. The see-and-be-seen set moved on long ago, but privacy seekers still make a beeline here. They’re drawn less by the property’s fabulous beach (though that’s reason enough to stay here) than by its exclusive location—in a well-fortified cul-de-sac in the ritzy Kahala neighborhood. But there’s a warm and fuzzy side to the hotel, too. A pod of dolphins has full-time residency in the hotel lagoon, and visitors of all ages can swim with them (for a fairly steep fee). Rooms have a preppy beach house vibe—raffia ceiling fans, linen loveseats—and many come with heart-stopping sea views.

This boutique hotel in the downtown business district exudes timeless class, with accents of wood and leather throughout. While the rooms are spacious and elegant, the most impressive features are the amenities. They rebooted the hotel’s historic 1915 beginnings as the Minneapolis Athletic Club with a massive modern fitness center, including a full indoor six-lane lap pool, running track, and racquetball, handball, and squash courts. The swanky hotel lobby serves food and drinks from the infusion specialists at Six15 and has a complimentary wine reception hour for guests each night.

This shopping plaza restaurant—set in the chilled-out, North Shore surf town of Hale‘iwa—evokes deeply nostalgic, yearning sighs from big-city folks. It is, quite possibly, the state’s best Thai food. But be prepared for cash only, erratic opening hours, no reservations, massive queues, lengthy waits for food once seated, and a highly variable menu. The chef-owner Opal quizzes patrons about their preferences... and then starts cooking. Man, are the results ever worth any slight inconveniences! Too hungry to wait? Stroll 0.2 miles north to tasty Rajanee Thai, which has a small dining room, as well as a takeaway window and outdoor picnic benches. Like many North Shore eateries, both establishments are BYOB: Long Drugs across from Opal sells adult beverages.

The cornerstone of the Kensington Street Precinct, at the heart of the funky Chippendale neighborhood, the Old Clare is the storied pub she used to be and so much more. Tonkin Zulaikha Greer Architects built a glass-and-steel walkway between the former Clare Hotel and the neighboring Carlton United Brewery building, both dating to the early 20th century, to create a 62-room boutique hotel that simultaneously feels historic and edgy. Original wood panels and brick walls blend seamlessly into spotted gum floors and nude-colored walls, exemplifying the creative reuse that pervades the Chippendale suburb, an inner-city district of galleries and cafés situated at the crossroads of Glebe, Redfern, Surry Hills, Chinatown, and the Central Business District. The design echoes other landmark Sydney restorations by Tonkin Zulaikha Greer such as the Paddington Reservoir Gardens and Carriageworks, an arts complex located just down the road. The Old Clare also brings two more standout restaurants to Chippendale, including the first Australian venture by Michelin-starred British chef Jason Atherton. Whether guests soak in the egg-shaped tub in their loft room, take a sunrise yoga class on the rooftop pool deck, or sip a “Ginny Hendricks,” a watermelon-dill concoction with bitters and Hendrick’s gin, at the midcentury-modern bar, they’ll have a story to tell. The Old Clare is a tale that keeps getting better.

In a city where gold-spired temples are much more ubiquitous than green space, Lumphini Park is a veritable oasis in the heart of Bangkok. Established by King Rama VI in the 1920s and completed after his death, the 142-acre chunk of tropical greenery is a treasured spot. One of the few parks of any size in central Bangkok, Lumphini is well used: In the morning, tai chi practicers arrive, while in the early evening, joggers monopolize the main path that runs around its perimeter. Even so, there’s ample room to get away from the crowds here. More than 30 species of birds flit among the park’s giant trees, and monitor lizards and turtles inhabit its waterways. Other attractions within the park include a public library, a youth sports center, and swan paddleboats in the man-made lake.

The “beautiful game” is dear to most Chileans’ hearts—you’ll even hear stories of families who could not afford a real ball and so fashioned one from layers of old pantyhose. Regardless of where the ball comes from, there is no limit to the enthusiasm with which locals embrace their national sport. When the Chilean national team is playing an international match, busy streets go quiet and a cab is impossible to find, but you’ll hear shouts erupt in unison from thousands of windows in a countrywide goal celebration. Julio Martínez Prádanos National Stadium can hold nearly 50,000 spectators; if you want a real sense of the game as experienced a la chilena, buy cheap tickets and find someone who can translate hilarious and highly off-color chants that fans spontaneously invent to goad or humiliate the opponent.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Soaking tubs big enough for two and double walk-in showers provide a clue that this beachfront all-inclusive, located less than 20 minutes from the airport on a peninsula just to the southwest of St. John’s Harbour, encourages families to look elsewhere. And while only the Premium Beachfront Suites have those particular romance-inducing amenities, there are other features, such as hideaway tropical dining, that will convince honeymooners and other couples that they have stepped into their own Gauguin landscape. Hence, the most secluded rooms, each with its own plunge pool, are called the Gauguin Cottages. Even among Antigua’s 365 beaches, Galley Bay’s is a visual standout that is longer and less crowded than most. The ocean here can get too rough for swimming, but the beach seldom fails to please for sunsets. Guests with limitless energy can choose from complimentary activities such as tennis, sailing, and stand-up paddleboarding. Or they can save their energy for honeymooning.