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You haven’t quite experienced the most authentic Reggae concert in Jamaica until you’ve been to Rebel Salute. While Sumfest gets all the press and is more commercialized, Rebel Salute—held every January—is Jamaica’s largest strictly-Reggae all-night show, headlining every single big Reggae music name you can think of. Now held on the north coast, on the picturesque grounds of Grizzly’s Plantation Cove, this well organized, alcohol-free event welcomes everyone from families to couples. Camp out by bringing your lawn chairs and blankets to indulge in the best of Reggae all night long, under the starry nights of the south. Food and soft drink vendors are present, of course, as are souvenir sellers. Tour operators do arrange group round trips to the event—inquire with Clive’s Transport--and hotels near the venue offer deals.

One of the delights of Valparaíso is exploring the colorful hillsides that ramble down towards the sea. Take the century-old funicular elevators Ascensor Concepción (Turri) or El Peral near the main plaza, constructed between 1883 and 1911. Once high into the hills of Cerro Concepción & Alegre, explore the meandering alleyways and cobblestone streets on foot. There are boutiques, cafés, mom-and-pop shops, old school bakeries, bars, restaurants, art galleries, and church bells tolling. It often feels more like a small village than a city. Climb up and down the many staircases often lined with bright graffiti. In the distance, the bay gleams in sunlight and the busy port never tires. At dusk, the lights twinkle like fairylight. Grab a table at a spot like Café Turri for a view of the sunset and a cocktail.

This Hawkesbury river boathouse looks like it’s come straight from a shoot with Vogue. Elegant and casual, fun and cheery, it’s worth taking a day trip to Palm Beach for. Red-and-white awnings hang over charcoal-painted tables where the white umbrellas don’t reach. Tin pots of orchids and tulips sit on stools. It’s lazy, albeit very busy (be prepared to queue), and linen, jeans and flip-flop clad diners order from a large blackboard. The signature beer battered flathead and chips are light and crispy, served in a little wooden box. The pot of herby Boston Bay mussels are small and sweet. For breakfast, the fluffy French toast, piled up with mixed berries and drizzled with maple syrup and mascarpone, and the Boathouse baked beans are hard to beat.

In 1931 Rowena Cade started to build a theatre on the cliffs in Porthcurno, Cornwall. Today there is a remarkable arena on the coast with just the sea and rocks as a backdrop. In summer the audiences are treated to performances from Shakespeare to Gilbert and Sullivan and many other dramas. The experience of watching a play in the open air with the sea crashing on the shore below is quite magical and a must do for anyone visiting Cornwall. When I last visited a pod of dolphins swam across the bay, completely distracting the audience. Take a picnic to eat during the performance as well as a rug and warm clothing. When the sun sets and darkness falls you can see the lighthouses and passing ships, but it does get cold.

• Neighborhood: Dupont Circle
• Why we love it: Recently renovated—and thoroughly stylish—public spaces that attract the best and brightest
• Loyalty program: I Prefer (Preferred Hotels & Resorts)
• From $215
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Fortunes and friendships change quickly in D.C., but the Dupont Circle Hotel has yet to go out of style. Set right on the roundabout itself, the eponymous hotel assumes a place of pride. Within, the site’s Martin Brudnizki–designed restaurant, The Pembroke—with its coral velvet banquettes, marble tables, and expansive outdoor terrace—has birthed a scene. Thanks to its location around the corner from Embassy Row, everyone from tony locals to visiting diplomats gather here to enjoy its mid-Atlantic-inspired menu, while the walnut-and-brass-clad Doyle is a whiskey bar fit for Ireland (home base of the Doyle Collection).

The 327 sleek guest rooms take similar advantage of their surroundings, most with large windows overlooking the circle. Upstairs, Irish designer Clodagh refreshed the penthouse suites, where spaces for relaxing include deep soaking tubs and private terraces with sun loungers. Clodagh also redesigned the lobby, which has the look and feel of a high-end apartment, thanks to details like a cozy fireplace and a look-through bookcase with brass accents. Best of all, though, is the feeling of walking out the front door in the morning and knowing that the capital is at your doorstep.

Read Afar’s full list of top hotels in Washington, D.C.

A challenging dayhike with a glacial-lake view at the end, and then Bratwurst-und-Bier for dinner: a perfect summer’s day in Washington State’s central Cascades! Take Icicle Creek Road from the town of Leavenworth to Eight Mile Road, then turn left and follow it up to where it ends at the trailhead to Lakes Stuart and Colchuck. This is a forested granite peaks wonderland. The switchbacks are shaded and crisscross streams; waterfalls will replenish your canteen...At 5800' you arrive at Lake Colchuck, glacially-colored beneath Dragon Tail Peak and Aasgard Pass (The NW’s Nordic heritage is evident here.) You might be gasping for adjectives, but you’ll understand why this area is called “The Enchantments.” Back down in civilization, feed your post-9-mile-hike-appetite with hearty Teutonic fare; Leavenworth is a mining-town-cum-Bavarian-hamlet--faux, but well-done. The pseudo-German architecture hosts many eateries, including München Haus--with its outdoor Biergarten, it will welcome even sweaty hikers. Several kinds of Wurst are available, served with local microbrews. Slake your thirst and savor the scenery... (About 2 1/2 hours from Seattle.)

The Cloisters, a museum devoted to medieval art and architecture, is a delightful respite from the hustle and bustle of NYC. This tranquil treasure is definitely worth a half day (or more) trip on your next visit. A branch of the Metropolitan Museum of Art, The Cloisters opened in 1938 and is located in Fort Tryon Park in northern Manhattan. Perched on a towering cliff, the museum offers commanding views over the Hudson River to New Jersey and the George Washington Bridge. The buildings include elements from medieval sites from Europe (primarily France) and renowned artwork includes the Unicorn Tapestries and the Annunciation Triptych, but the heart of the museum is the cloistered garden. This lush space consists of an interior courtyard surrounded by covered walkways. The flowering garden within invites contemplation and appreciation of a different time. The Cloisters includes a broad terrace with expansive views across the Hudson. The view is so prized that in 1901, J.P. Morgan purchased 12 miles of the New Jersey coastline to protect it from excessive quarrying and in 1933 John D. Rockefeller, Jr. donated 700 additional acres of NJ to preserve The Cloisters’ view. Be sure to include time in your visit to explore beautiful Fort Tryon Park.

Sunday brunch at Perry’s is not your usual run-of-the-mill affair. Yes, there is an all-you-can-eat buffet bar filled with typical brunch fare. Yes, there are the usual boozy drinks to go with your brunch meal. Yes, there is music piped over stereo speakers. But this is far, far, far from an ordinary brunch because it has fabulous drag queens to entertain you while you eat! Perry’s Drag Brunch is among D.C’s most loved institutions. There are two seatings each Sunday and they don’t take reservations. The line forms outside around 9am for first seating which is at 10am. Make sure you’re in that line. As soon as the doors open, ask to be seated toward the center of the room—the bad seats are on the periphery. A split second after you get to your table, throw your stuff down and RUN to stand in the buffet line. After you get your food, then flag your waiter down to get your drinks. At about 11am, the show will begin. The drag show features queens that are campy and witty, and the show is raunchy and HILARIOUS! Perry’s Drag Brunch is definitely not for the timid, though! You may get called out, and next thing you know you’re a part of the show. Whatever happens, you can be certain your friends will have captured the moment on their smartphones and before the red blush leaves your face, they will have already posted it up on Facebook! It’s all in good fun! Just remember to bring along a wad of $1 bills for tips. The ladies do work hard for the money!

The story behind the founding of the Museo del Juguete Antiguo México (Museum of the Antique Mexican Toy) is almost as charming and intriguing as the collection of toys itself. Roberto Shimizu, Sr., who founded the museum with his son, Roberto Shimizu, Jr., began collecting toys when he was a child and in the decades since, has amassed a collection of literally millions of toys. He decided it was important for the collection to be accessible and visible to the public, partly to document the history of toy-making in Mexico and the world. The space occupied by the museum covers several floors, but it’s barely large enough to showcase all of Shimizu’s treasures, which he has catalogued carefully in numerous notebooks and binders. That may be hard to believe, given the fact that the museum is crammed wall-to-wall and floor-to-ceiling with toys of every type: from plastic soldiers to board games and Barbies to model trains. The museum is a cabinet of curiosities for the kid in all of us.

OK, we didn’t exactly go far for dinner. We were staying in the Ace Hotel, just two doors down, but we were jet-lagged and hungry. We had seen many people hunched over enormous sandwiches through the window of this traditional-style deli at lunchtime, and we were surprised to see they were still open at 7:30pm. So we went in. We liked the simple, homely decor. We liked the smells emanating from the kitchen. We liked the fact that when we decided not to have sodas, the matronly server said, “Nah, you don’t need them honey, I’ll just keep the water coming.” We looked at the menu. We ordered two hot dogs, and a side order of pastrami fries. The waitress looked at our innocent little faces and told us we’d only need a half portion, as a whole portion of pastrami fries was “pretty big.” Our hot dogs arrived. They were delicious, and stacked with homemade relish. Our fries arrived. The “half portion” was so large we laughed out loud, then stuffed ourselves with the delicious cheese-pastrami-potato concoction until we should by rights have passed out. We got the check. It came to $14. We blessed Kenny & Zuke’s, and all who sail in her.

While scouting out the remaining lighthouses left standing on the Oregon coast, I was lucky enough time my visit with two gray whales. There’s a vintage whale watching station just across the parking lot at the Umpqua River Lighthouse and with a few quarters, I was able to see the action. By flipping through my guidebooks, I learned that morning is the best time to scout for the views of the mighty whales, that like to hang out at the mouth of the Umpqua River where it empties into the ocean. In the morning light, the sun is at your back at the viewing station, meaning you can spot the whitecaps that the whales create (instead of the ones that the wind and waves create later in the day). At the station, you’ll find a sign with a few helpful suggestions to spot these magnificent creatures. You’re instructed to look for puffs of vapor that seem to hang in the air, just above the water. Those spouts usually rise twelve to fifteen feet into the air and when you spot one, you’re bound to see several in the same area. Soon, you’ll be able to observe the head, back and flukes as the whales roll on the surface.

Despite its size (10 square miles) and population (fewer than 170 permanent residents), Little Cayman enjoys a worldwide reputation among serious divers. The island is renowned for its exceptional underwater visibility and vertigo-inducing walls, especially north-shore Bloody Bay. Dive boats flock to Three Fathom Wall, where bulbous coral heads teeming with fish rise to within 10 feet of the surface. Snorkelers are likely to encounter schools of blue tang and stoplight parrot fish, as well as hawksbill turtles and nurse sharks.

At Lizard Island, luxurious amenities meet an ecologically diverse island paradise. The sole resort on the island, the exclusive spot features 40 rooms as well as 24 private beaches, all but guaranteeing your own pristine sliver of paradise. Accommodations range from posh villas set apart from one another (including the two-bedroom, cliff-top villa, with its 26-foot pool and endless views of the Coral Sea), to garden-view rooms with private terraces and pathways leading directly to Anchor Bay beach. Furnishings follow a tranquil white-and-gray color scheme, while amenities include LCD smart TVs and Apple docking stations. Guests also receive their own motorized dinghy, standup paddleboards, clear-view sea kayaks, and snorkeling gear for exploring Giant Clam gardens and the schools of brightly colored fish in the surrounding waters. The more adventurous can even arrange for private deep-sea dives to locations accessed exclusively by the Lizard Island Marine & Dive team, ensuring you’ll have the coral reefs all to yourself.

An antidote to hectic modern life, Travaasa Hana, on Maui’s remote eastern coast, feels like a step back in time. There are no televisions, radios, clocks, or air-conditioning (ceiling fans and panoramic sliding doors capture ocean breezes) in nearly all of the 70 cottages and suites, but you won’t miss them. Your days will be spent soaking up Hawaiian culture, whether that means fishing with throw nets, making traditional ti leaf leis, or enjoying an open-air ukulele lesson. Of course, no visit to these parts is complete without a journey along the legendary Road to Hana, which lies to the north and west and promises primordial views of waterfalls, gardens, and secluded swimming holes. Upon your return to the resort, savor the fresh-caught specialties at the Preserve Kitchen & Bar, overlooking Hana Bay.

One of Dubrovnik’s oldest fortresses stands atop a 100-foot rock, guarding the western land entrance to the Old Town. Vigilantly turned toward Venice, it serves as a monumental tribute to Dubrovnik’s foresight, encapsulated in the motto of the Ragusan Republic engraved above the main entryway: “We do not sell our liberty for any gold in the world.” After entering the Old Town through the Pile Gate, walk down to Kolorina Bay and climb the stairs to the fortress. Because it’s far less busy than the city walls, the theatrical space offers a more intimate way to experience Dubrovnik’s history and charm, with breathtaking views to boot.