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Given Ipanema’s highly fashionable status, it’s no surprise that its first luxury hotel comes courtesy of aesthetic superstar Philippe Starck, who outfitted the property—his first in Brazil—with mid-century modern furniture evoking Rio’s Bossa Nova glory days. Rooms include luxe bedding, high-pressure showers, and complimentary flip-flops from Brazilian brand Osklen, while public spaces feature Starck’s Surrealist “L’oreille Qui Voit” (“ears that see”) mirrors to maximize water views. In fact, the entire hotel takes advantage of its oceanfront location—even the meeting space has a sea-view terrace.

The Fasano family made its name a century ago with Italian restaurants so, naturally, the hotel’s Al Mare takes a Mediterranean bent, serving expertly prepared seafood under sparkling Murano chandeliers. Elsewhere in the hotel, the modest fitness center offers complimentary personal trainers to guests, while the Asian-influenced spa features a Vichy shower on the roof. The surrounding beach scene may be hot during the day, but the Fasano’s rooftop infinity pool and bar—exclusive to hotel guests—is the place to be come sunset. Grab a drink and watch the sun go down over Aropador, Ipanema, and Leblon beaches and Rio’s iconic mountains.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

Viernes Culturales is a local Miami event in Little Havana, where restaurants, galleries, clubs and street vendors get together on the last Friday of every month for a cultural art show. Local merchants and artists set up on the streets of Calle Ocho to turn it into what looks like a street fair. The City of Miami sets up an event area in the alley next to the Tower Theater to host DJs, performers, artists and sellers. Sponsors set up booths around here and offer free tastings and gifts. There are many live performances that occur throughout the day and night, but people dance throughout the streets during the entire festival. Many nightclubs serve drinks and vendors give out samples. Be sure to check out the expansive list of restaurants before choosing. I suggest going on a food crawl to really explore the Cuban American culture in Miami.

Stroll inside the Errol Flynn Marina, located right in Port Antonio town, for a waterfront respite along manicured lawns and sailboats. Enjoy an afternoon “I-Scream” cone from the on-site Devon House, a household name in Jamaica. There are public benches by the water, as well as bars and restaurants. If you can, stay long enough to enjoy the sunset.

My morning routine in Aspen always starts with a run along the Rio Grande Trail. The trail is easily accessed from downtown and stretches 41 miles between Aspen and Glenwood Springs with an elevation change of 2,120 feet. It used to be an old railroad corridor before it was converted into a mostly paved trail for cyclists in 2008. I start my run in Aspen and run out and back for about six miles. That stretch of the trail takes you past the Aspen Art Museum (which is moving locations in 2014), the John Denver Sanctuary, and stunning homes nestled along the river and up in the mountains. In July and August the wildflowers pop with color and if you leave early enough there’s a good chance you’ll spot deer, chipmunks, and other wildlife.

Those in search of sublime culture in an exuberant natural setting will find an ideal refuge in the Instituto Moreira Salles, a modernist residence hidden on a lane above the Gávea quarter that’s home to a cultural center. The delights on offer at this off-the-beaten-path spot—visual-arts and photography exhibits, literary salons, film series, and a stunning garden by famed landscape designer Burle Marx—are made all the more amenable by a restaurant as well as petite art– and Rio-focused bookstore. The IMS also happens to be the city’s most extensive photographic archive. If you’re looking to learn Rio history, a visit to this rare gem—nestled into the Carioca jungle—is a must.

Though few tourists venture to Kingston, the capital and hub on the eastern coast of Jamaica, music fans should make the day trip to visit Bob Marley’s former home, now a museum dedicated to Marley’s life and impact on the world. A guided tour of this museum takes about an hour and a half and includes a 20-minute video presentation. Even devoted reggae fans will likely learn more about Bob than they ever knew. Exhibits include multiple awards, guitars, and his bed with an engraved headboard depicting a lion.

Few venture this far east in Jamaica, but those who do will find one of the most authentic sides of the island, and the most secluded of getaways. A charming fishing village about thirty minutes past Port Antonio, Long Bay is as peaceful and scenic as it gets, with just a handful of affordable, casual guesthouses perched atop dramatic cliffs and overlooking a long stretch of deserted beach. No frills here, just nature and culture. The fresh ocean air, the roadside fresh seafood shacks and friendly locals will have you staying longer than you planned. Be sure to drive along the coastal highway and head as far as Manchioneal, another stunning fishing village that feels thousands of miles away from the touristy side of Jamaica.

The actual name of the place is Adega Rio Douro (since it’s facing the river) but everyone knows it by Tasca da Piedade, named after the owner Mrs. Piedade. It’s also known for having “fado vadio” - traditional Portuguese music, here sang by non-professionals every Tuesday in the afternoon from 4pm until 7pm. While the music flows you can try a lot of Portuguese “petiscos”, such as stewed chicken guizzards, meat croquettes, “bifanas” and the crown jewel “iscas de bacalhau” - boiled codfish loin enveloped in a parsley omelette. The symbiosis between food and music is guaranteed, as everything here is done with passion. You might even be lucky to listen to the owner singing a few “fados”.

Prana began as a low-profile boîte, short on tables but long on creativity. Word spread quickly and soon, long lines trailed out the door. Prana then merged with O Quintal Zen, a health-food restaurant in one of Rio’s most charming neighborhood, Jardim Botânico, and the result is a winning fusion of vegan food, meditation, and serious yoga classes. In the new larger space, the focus is still on quality. Every day, the chefs offer two vegan, gluten-free specials alongside several heathy desserts, so you can enjoy a great lunch before a trip to the Botanic Garden or the beach.

Tastee and Juicy may be the two most popular brands of Jamaican patties, but one definitely should not miss out on the super premium patties on offer at Devon House Bakery. Set on the grounds of the historic Kingston mansion, just a few minutes from such notable area hotels as the Courtleigh, Jamaica Pegasus, and the Knutsford Court, Devon House Bakery espouses some serious Old World cafe charm. A fine selection of sinful sweets – brownies, butter cookies, cakes, muffins – awaits inside. So too does one of the most amazing Jamaican patties I’ve ever tried. Options go well beyond the usual beef with fish, pork, shrimp, and lobster elevating the typical Jamaican patty to new heights. The best choice, though, is the curry goat. Spicy and succulent, the Devon House goat patty melts in your mouth while warming your soul. Pure, delicious niceness and most certainly the very best Jamaican patty I’ve ever had. Don’t miss it!

Located along a stretch of coastline that’s sometimes called the birthplace of jerk cuisine, the Boston Bay Jerk Center is hard to miss. Various meats are cook on open pits using a technique that may explain why jerk never tastes so good at home: Uncured pimento logs are placed over a bed of hot coals, and the meat is laid directly on the green logs. The whole operation is then covered up by a sheet of corrugated zinc and cooked until it’s black on the outside and tender underneath. You can place your order by the quarter, half, or full pound. Don’t forget to add jerk sauce, which you can also buy by the bottle as a souvenir.

Going to dinner at Little Ochie is as fun as it is delicious. Pick your dinner—from a cooler of freshly caught fish—by species and by weight, then pick the style in which you’d like it cooked: jerk, grilled, escoveitch, and more. Pick a side of bammy, a thick round of cassava bread, to go with it. Your next decision is where to eat—head outside and choose a picnic table under one of the thatched huts carved in the shape of a fisherman’s canoe. The combination of beachy atmosphere and great fish makes this relaxed yet lively slice of Jamaica well worth the hour-long drive from Treasure Beach.

An Art Deco landmark on Rio’s famous stretch of sand, the Belmond Copacabana Palace has set the standard for visiting celebrities and discerning guests for nearly a century. In the luxurious rooms, muted colors, original artwork, and botanical murals serve as the backdrop for views of the ocean and black-and-white boardwalk. Outdoors, guests can lounge around the almost Olympic-sized pool—much like Marilyn Monroe once did—or take advantage of the hotel’s beach service, complete with assistants to watch your belongings while you swim. Visitors also have access to the hotel spa, which uses Brazilian fruits and Amazonian ingredients in its treatments, as well as an impeccable concierge team, which can arrange exclusive sunrise visits to Christ the Redeemer before it opens to the public.

The restaurant and nightlife scene may be hotter in Ipanema these days but Belmond guests are spoilt for dining choices. Hotel Cipriani Restaurant—named for the Copacabana’s sister hotel in Venice—serves elegant Northern Italian, while Pérgula is bustling day and night thanks to caipirinha cocktails prepared tableside and a menu of Carioca favorites like grilled seafood and steaks. For an award-winning meal, there’s also Mee, which holds a Michelin star for its haute Pan-Asian dishes and extensive sake selection.

Over the last several years, Madrid‘s river redevelopment has really come together. What used to be sludgy is now sparkling, with walkways and bridges intertwined along the river, with kids playing, people jogging and chatting. A great place to get away from the crowds, even in the winter. Tourists don’t really know about it, which makes it even better. Go at sunset so you can watch the lights of the city come on and the moon rise. Start on the south side, by the new Matedero arts center and move your way up north to the Royal Palace. Delightful way to spend an early evening.