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This stunning white-sand stretch, just a five-minute drive east of Port Antonio, is the only beach in Jamaica with waves high enough to surf. Boston Bay is also one of the few remaining public strands on the island. It continues to attract more locals than tourists and as such is nearly vendor-free. You can watch kids splashing about on their boards, or you can rent your own for a Surfing 101 lesson. Be forewarned: As at many beaches, sometimes the waves are flat, but you can console yourself with a short stroll down the beach to the famous Boston Bay jerk chicken stands.

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.

Few things characterize autumn in North American more than apple picking, apple pies, and apple cider. If you feel like connecting with nature and experiencing a Canadian tradition, head to the western tip of the island and the Labonté Orchard for a wee session of apple picking. There is a small admission fee of $2, and you are free to stay on site for as long as you like. If you don’t go for the apple picking, go for the heaven-sent desserts at the on-site café. The apple crumble will make you a believer.

Albertha Grant never set out to win a James Beard Foundation award and win the adoration of international magazines and patrons—she simply cooked good food and served it to people in her North Charleston neighborhood. But amidst the last decade’s gold rush around Charleston cuisine, Bertha’s shines in both its authenticity and flavor. It’s a classic soul food joint, with daily meat-and-three specials like fall-off-the-bone fried chicken, sumptuous pork chops, and collard greens that perfectly balance savory and sweet (there’s plenty sweet in the ice tea for everyone). The neighborhood is predominately African-American, and locals still line up here for lunch along with out-of-towners and Peninsula-based workers seeking Southern food done right. The late namesake’s daughters and granddaughters run the counter-service place now, efficiently taking orders to keep the line moving on busy weekdays.

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

Following a much-needed $60 million makeover in July 2022, the Park Hyatt Chicago is once again a contender for one of the best hotels in town. Located in the bustling Magnificent Mile neighborhood at 800 N. Michigan Avenue, the storied property has been a landmark destination since it opened in 1980 as the first property to bear the Park designation. The renewed sanctuary now delivers a true sense of place, with a refreshed lobby design that’s more of an urban living room, an updated Library, and a vibrant new art program spotlighting some of Chicago’s most talented creatives. Critically, the hotel’s signature restaurant NoMI (named for the location on North Michigan Avenue) now has three different concepts: NoMI Kitchen, which emphasizes American cuisine with French techniques, NoMI Garden, a terrace space that’s ideal for lunch, and NoMI Lounge, which includes a six-seat sushi bar.

The Park Hyatt Chicago, facing ever stiffer competition from newer luxury hotel entries in the Magnificent Mile orbit, nevertheless remains a great choice for families because of the central location optimizing sightseeing and kid-heaven treats. Budding geologists will love the geodes, minerals, and marine fossils in the lobby alcove. Chefs at the seventh-floor NoMI restaurant, known for fine wines, city views, and standout American contemporary cuisine, take young foodies to the open kitchen’s soft-serve ice cream dispenser. The 7,000 square foot fitness center includes a 25 yard lap pool with skyline views, or borrow a complimentary Jamis commuter bike to ride the scenic Lakefront Trail four blocks east on the beach side of Lake Shore Drive. Guestrooms have notable design flourishes such as padded window seats, Eames chairs, and Mies van der Rohe–designed Brno desks from which to view the city’s famous architecture. Pets are welcome, and the hotel donates 100% of its standard pet fee to one of the city’s largest animal shelters.

Have you ever had a drink while standing at the top of a 1,700-foot vertical drop, as the sun sets into the ocean? That’s what you get at Lovers’ Leap, less than a half-hour’s drive from Treasure Beach. Pay a small entrance fee and walk through the bar to reach the balcony with the jaw-dropping view. Of course, there’s a legend to go with the name of the cliff: Two enslaved lovers jumped together from this spot to their deaths to escape from their colonial master who wanted the girl for himself. A wood carving of the lovers stands just outside the entrance. The sunset panorama here is arguably the most stunning view in all of Jamaica.

Bourbon Beach, a popular beachfront music venue on Negril’s Seven Mile Beach, hosts local bands, reggae artists, or themed parties on an almost-nightly basis, to the delight of tourists and locals. People-watching at Bourbon Beach is great, the drinks stiff, and you get to dance in the sand to live reggae in Jamaica. The music starts up around 10 p.m. and continues until 2 a.m. Upstairs, a wide-open deck is open for stargazing or getting away from the crowd. Cover charges are only collected on nights when a recording artist performs. Alfred’s, nearby, is another longstanding option, offering live local acts three times a week for a US$5 cover.

Jamaica’s most touristy site—famous for being featured in the James Bond movie Dr. No.—is also one of its most beautiful, in spite of the countless bodies that visit and attempt the climb daily, both locals and tourists. The view of the falls is spectacular. And call it cheesy, but it’s actually fun trying to ascend stone steps while being splashed by 600-foot-high powerful falls that cascade down into a jade pool. Grab a licensed guide on-site if you need one, otherwise latch on to one of the human chains you’ll spot when you arrive. The falls are just a stone’s throw from Ocho Rios, so any route or shared taxi will make a stop here for a few bucks.

Located across the way from Half Moon Resort, Sugar Mill Restaurant is set on the grounds of an old plantation. Couples and small groups dine at candlelit tables either on a covered terrace or out on the lawn, and the splashing of the mill’s waterwheel and the chirping of crickets are an accompanying sound track to the top-notch service and Caribbean fusion menu. Order a bottle from the well-stocked wine cellar, visible as you enter the restaurant. For special occasions, a private table beside the waterwheel can be reserved. (In the mood for a lighter, slightly more casual meal? A tapas menu is available in the restaurant lounge.)

If eating huge plates of pork, deciphering local slang, and snowshoeing through the woods of Québec can’t bring two siblings together, what can?

The laid-back restaurant Carbon Caribbean Cuisine takes you on a culinary journey around the Caribbean. You can order typical dishes from Cuba, Jamaica, Puerto Rico, and, of course, the Dominican Republic. Popular with locals, Carbon offers a glimpse of island life beyond the beaches and resorts.

Few places in North America are anchored in a heritage like the Pueblo of Taos. This is the longest inhabited living arrangement in the US. The Pueblo still has ten families of around 150 native people working to maintain the culture and the adobe architecture for generations to come. A living artifact, the past and present form a delicate harmony to produce a unique travel experience. The environment says a lot about the sustainability of this community. Tucked up against the Sangre de Cristo Mountains, with the Rio flowing through the center of the Pueblo, the inhabitants have maintained their lifestyle through wars, disease, cultural genocide and environmental impact to survive. From the efficiency of their adobe walls to provide comfort against extreme heat and cold, to the guiding wisdom of elders to keep the Pueblo vibrant, the way of life preserved within these walls is a testament to the strength and vision of native people, connected to this land with over a thousand years of tradition.

Reach Falls is an off-the-beaten-path delight. Located up in the John Crow Mountains on Jamaica’s east coast, this 30-foot jade-colored cascade tumbles into several pools in the surrounding rain forest. You’ll need a bathing suit and a waterproof camera to capture the natural splendor. Local guides are available to help you make your way across the swimming holes and levels, and show you the best spots. Or you can explore it solo. Because of its distance from tourism spots, there are no crowds, no harassment, just an entrance fee to your very own Garden of Eden. On-site changing rooms are available as you exit by the parking lot. Small fun fact: The falls play a minor role in the 1988 Tom Cruise movie Cocktail.

North of Georgetown, nestled on 5.5 acres of woods and gardens, this obscure museum is the former mansion of Geico Insurance executive and avid art collector David Lloyd Kreeger and his wife, Carmen. Designed and built by renowned architect Philip Johnson, the International Style masterpiece displays the couple’s collection of 19th- and 20th-century European and American art, and traditional African and Asian art, with an outdoor sculpture garden to boot. Highlights include paintings and sculptures by Picasso (their favorite artist), Renoir, Monet, Van Gogh, Cézanne, Rodin, Chagall, Mondrian, and local talents. The museum also functions as a venue for after-hours classical and jazz concerts.

Few visitors venture to Duncans Bay, a small town in northern Jamaica, halfway between Montego Bay and Ocho Rios. But its public beach, called Fisherman’s, is one of the best for a local vibe. The scenery is straight out of an old Caribbean postcard: kids play in the distance, colorful fishermen canoes rest on shore, and a ramshackle bar along the wide golden sands attracts the usual neighbors. Show up mid-afternoon, when the grill and some background music get started, while the waves splash and the sun prepares to set. The slow rhythm of this area, away from the resorts, vendors, and tourist trails, will make you want to stay for hours. No problem—there are local guesthouses a stone’s throw away.