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Quirky is the word for Castle Leslie Estate in Monaghan—near the border between Northern Ireland and the Republic of Ireland—where rooms are arranged at the end of higgledy-piggledy corridors and long flights of stairs. The winding layout and overstuffed armchairs in the lobby make the vine-swathed, 19th-century castle feel like a family residence—and it feels even more homey when you see the castle’s nonagenarian owner, Sir John Leslie, Fourth Baronet (or Sir Jack to guests), chatting with visitors in his pajamas around midday.

There are a thousand acres to explore, three lakes to row around, forests to get lost in, streams to follow, and horse trails to trot along (starting in the equestrian center and livery near the main house). So at the end of the day there’s nothing left to do but sit by the fire and engage Sir Jack in a long chat. Rooms are scattered throughout the estate: in the castle, of course, but also in the former hunting lodge, stable mews, and village cottages.

This tiny hideaway overlooking the sea near Port Antonio originally served as a live-in recording studio for performers such as No Doubt, Alicia Keys, and Amy Winehouse. Although recording sessions still go on, Geejam is now a seven-room hotel, its guests often honeymooning couples acting out fantasies having nothing to do with rock and roll. Geejam’s cabins, especially, are very private, and guests sometimes spend days taking meals on their veranda and splashing in their outdoor Jacuzzi without being seen by anyone but the staff, who appear only when called. Of course, who wants to stay hidden forever when the Bushbar restaurant promises convivial chitchat, an occasional game of pool, and even live music? Not to mention that the hotel beach, in a cove across a road at the bottom of the property, promises four-poster sunbeds and, yes, Wi-Fi.

Yam is a unique park that truly makes Berlin a city of the free. Created by rastafarians, or rugged nomad expats from Jamaica, Ghana, and Africa, they’ve created an environment that lives up to their dreams; a carefree zone where the only thing that matters is a cold beer, good people, music, food, and sports. Once inside, you walk through lots of sands with implanted picnic tables. Rastafarians serve food from stands that stems from a background of Caribbean or african roots. Cold local beer is served by a bar overlooking the ocean and sport fields are open for any basketball or soccer takers. Come by day to relax under the sun or come by night to dance through a cultural endemic.

One of the newest - and most popular - attractions to hit these shores, “Xoximilco Cancun,” is a floating fiesta, offering entertainment, colorful anecdotes, history, good food and drink - and three hours of sheer delight. Thanks to the entrepreneurial genius of the Xperiencias Xcaret visitors can experience an improved recreation of Mexico City‘s renowned Xochimilco. Both are replicas of the canals in the ancient Aztec capital of Tenochtitlán and the lake it was founded on. A series of floating gardens (chinampas) separated by canals became the marketplace for flowers and agriculture, which were transported in flat boats known as trajineras. The party in Cancun begins at 7: 30 p.m., when you’ll be given the name of the boat you need to board. When the marine bell rings, you head off on your dinner “cruise,” featuring delectable Mexican cuisine and local refreshments, including Tequila. As you glide along the canals, an assortment of musical ensembles glide by, treating you to traditional live music, including: mariachi, bolero trio, jarocho quartet and marimba medleys. A small gift shop offers plenty of souvenir options Recommended for children 10 and older.

This Little Burgundy mainstay is the headquarters of chefs David McMillan and Frédéric Morin, the acclaimed and enterprising minds behind an evolving blackboard menu that has been known to feature smoked meat croquettes, house-cured ham with truffles, lobster spaghetti and horse meat steaks. The duo is known to do absolutely everything in-house, even brew their own beer and distil their own absinthe. Stroll down Rue Notre-Dame, past their other restaurant, Liverpool House, to the nearby Lachine Canal after an evening at this inviting space with vintage wooden chairs, leather banquettes and a permanent air of celebration.

With its thatched roof, bamboo bar, and surfboard decor, this beloved watering hole—often voted Maui’s best bar by locals—checks all the tiki boxes. Head here for live music, lanai seating, and late-night dancing, plus fun and fruity rum cocktails like mai tais, zombies, daiquiris, and piña coladas. Beyond its drinks, South Shore Tiki Lounge was recognized by the state of Hawaii as an outstanding business for its regular fund-raising efforts, which benefit local organizations like the Keiki Cupboard, Hawaii Wildlife Fund, Maui Humane Society, and Hawaii Animal Rescue Foundation. All that to say, you can feel good coming here to wash down a massive chili-cheese hot dog with a lychee-watermelon martini.

Among Charleston’s two dozen thriving breweries, Revelry may have the best digs. It’s located in the peninsula’s NoMo neighborhood and sports a spacious, laid-back rooftop deck bar that’s perfect for viewing sunset over the Holy City skyline. The whole place is adorned with art—including on its cans’ labels—by recognizable local artist, Chris Kemp. Fortunately, what’s inside the cans is equally memorable. Brews like “Gullah Cream” and “Poke the Bear” (an American Pale) are among the city’s signature ales for any beer lover seeking the best of Charleston. Happy hour features live music Friday through Sunday, making Revelry a go-to gathering place.

On the ultra-exclusive island of Mustique, Basil’s Bar is a stargazer’s paradise—and not just at night. It’s a favorite of celebrities, meaning you never know just who will be seated at the next table. A series of roofs cover the open-air deck to shade diners from the hot sun and occasional shower as they enjoy tropical cocktails and freshly grilled lobster. Come for the dance party on Wednesday, the happy hour on Thursday, or the sunset jazz every Sunday at 5:30 p.m. Basil’s also hosts the Mustique Blues Festival at the end of January, with live music each night for two straight weeks.

Part restaurant and part performance venue, the Rendezvous is a full night out in one cozy spot. The restaurant has typical bar food (burgers, salads, deep-fried snacks) that’s basic but good; happy hour goes from 3-6 pm daily with food specials. The tiny Jewelbox Theatre is an intimate cabaret-style theatre, where you’ll find everything from burlesque to comedy variety shows to live music and theater. They also have two excellent private rental rooms for parties. Upstairs, the Red Velvet Lounge looks out onto the main dining floor and has its own sound system. Downstairs, the basement-level Grotto is a dark, red-lit cave with its own private bar and plenty of room for dancing.

Situated oceanfront on Collins Avenue in the shadow of The Setai (South Beach’s tallest and most expensive hotel), Townhouse is a humble Art Deco concrete building trimmed in red with two very cool venues hidden inside, a subterranean ramen lounge and a laidback rooftop bar. K. Ramen. Burger. Beer excels in all of its eponymous categories and also serves delightful poke bowls and chicken wings, while The Cape is a surprisingly rare rooftop perch in South Beach with a laidback bungalow atmosphere playing host to live music.

The oldest bar on the island, Flor de Oriente was established in 1935 and remains a favorite for both island natives and repeat visitors. It’s a great spot to grab a happy hour drink away from the crowds at the beach, as well as a bite to eat, like locally caught fish, burgers, and bitterballen (a deep-fried Dutch meatball and the perfect accompaniment to the lengthy beer list). There’s usually live music on the outdoor patio, too, from jazz to oldies to the ever-popular house band Flor de Oriente Social Club, which plays merengue and salsa every Friday.

A compound-like hideaway on a leafy street a block from trendy South Congress Avenue, Hotel Saint Cecilia is a retro-glam love letter to the 1960s and ‘70s rock music scene, named for the patron saint of music and poetry. But that doesn’t mean that rock stars smash guitars and throw ragers here (unless they rent out all 14 rooms, of course); unlike at its nearby sister properties, Hotel San José and Austin Motel, only guests and club members are welcome at the lounge, a laid-back affair with a Parisian-café–style patio, chesterfield sofas and a fireplace indoors, and craft cocktails and gourmet small plates. Between the 1888 Victorian main house—originally inhabited by a descendent of Davy Crockett—and verdant grounds that hide private porches and a serene pool, the hotel feels more like an impossibly stylish artists’ retreat than a celebrity getaway.

Each distinctively decorated room is larger than many an apartment, and seems ripped from the pages of a fashion magazine photoshoot. Every detail has been thought through, from the refreshing Grown Alchemist body care products to the Swedish Hästens mattresses (the hotel is the only one in North America with them in all rooms) to the impressive library of LPs to borrow. Everyone’s a rock star, here.

Set on the western side of Circular Quay, the Museum of Contemporary Art Australia (MCA) is the country’s leading institution for modern art. While access to touring international exhibitions from the likes of Tatsuo Miyajima and Annie Leibovitz incurs an entrance fee, the permanent collection of more than 4,000 contemporary works by Australian and Torres Strait Islanders, from Gary Carsley to Lena Yarinkura—plus a rare collection of artist notebooks, music, letters, and sketches—is always free. Come on Wednesday night when the gallery is open until 9 p.m., or for the adults-only Art Bar on the last Friday of the month. The rooftop café offers occasional live music and DJs plus glittering views of the Sydney Opera House and Harbour Bridge after dark.

Every day millions of people walk down Istanbul’s famous Istiklal Street unaware of the nearby terrace restaurants offering magnificent cuisine and divine views of the Bosphorus Strait—among them, Divan Brasserie Beyoğlu. Opened in 2014, the restaurant excels in plating timeless recipes with modern touches. Take a seat here for lunch or dinner and peruse a menu of regional dishes such as the Albanian-style liver and pan-seared lamb served in eggplant puree along with gourmet pizzas, beef burgers, and seafood dishes. Istanbullus (Istanbul residents) will say you haven’t dined in Istanbul until you’ve dined at a rooftop terrace overlooking the city. Do them proud at Divan Brasserie Beyoğlu. To find it, look for Koć University on Istiklal Caddesi and follow the discrete signage and let the glass elevator take you the rest of the way.

Owned by Terry Kaljo—a former model and founder of the Contemporary Hotels collection of upscale rental homes and villas—the Medusa Boutique Hotel offers 18 unique accommodations in Darlinghurst, an eclectic area and the epicenter of Sydney’s gay community. The 19th-century home is filled with wacky touches, from red Alice in Wonderland–style carpeting that runs up the grand staircase to pastel-pink walls studded with maple leaves in the entryway. The midcentury-modern rooms—with their retro primary colors, geometric patterns, and vintage chaises longues—attract fashion, media, and design professionals looking to get beneath the surface of one of Sydney’s liveliest neighborhoods. But there’s still the opportunity to relax, as guests can settle in next to the fireplace in the lobby to read the newspaper, enjoy a complimentary pastry, or make new friends. Longtime staff members offer the kind of local knowledge and personal attention that keeps guests coming back.