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Those who just stumble upon the Hundertwasserhaus apartments in the Third District will likely be wowed by the buildings. Friedensreich Hundertwasser’s funky, mid-1980s organic housing complex is weird and gorgeous with a wavy, eclectically painted facade that looks like something out of a cartoon. With trees growing on its terraces and roof, it’s the antithesis of staid imperial Vienna. A freethinker if there ever was one, the artist, architect, and environmentalist Hundertwasser could be called Austria’s Gaudí. Visitors can learn more about him in the ground-floor café. Nearby, Hundertwasser designed the Kunst Haus Wien art museum out of an old Thonet furniture factory, while up the Danube Canal an incineration plant’s chimney got the Hundertwasser treatment with trippy colors and a funky golden ball on top.

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.

With just a few tables and a handful of barstools, this bar may be tiny, but it packs a lot of character into its diminutive space. Walls are decorated floor-to-ceiling with a mix of beer posters and racy street art; at the small wood bar, eight curving brass taps dispense top-notch Belgian-style draughts like La Chouffe and La Trappe. Around 50 specialty beers are also available by the bottle, many of them rare craft brews. During evenings, the bar even manages to squeeze in a DJ, who spins funky old-school jazz.

Watching the sun set on Jamaica‘s west coast is a bona fide activity. The island’s red skies are a sight to behold. I have yet to experience a better Caribbean sunset than in Jamaica. From Montego Bay all the way to Negril--famous for having the best--to Whitehouse, get your camera and Red Stripe ready for the last hours of daylight. You won’t lack for choice of seafront bars or scenic spots--from the trendy Pier One in Montego Bay to the wooden shack watering holes along Negril’s West End cliffs. Wherever you end up, there’s a very good chance you’ll get hooked on this daily sunset viewing routine.

The only building on sheltered Apantima Bay, this funky beach bar with rooms is one of the reasons the tiny island of Antiparos has suddenly become fashionable. Hanging with the skimpily clad in crowd doesn’t come cheap: If you’re not staying in one of the nine quietly chic suites, you’ll have to fork out handsomely for a sun bed. The payoff is chilling under juniper trees with a detox smoothie, idly watching athletic beach babes paddleboard into the sunset. There’s an alfresco massage and yoga pavilion; a stylish boutique where you can pick up caftans, scents, and sandals; and a 26-foot bar for sundowners and tuna burgers with wasabi mayo.

Taf Coffee started out as a family-owned coffee roastery in the 1990s then quickly moved beyond Greek brews to becoming Athens’ main source for international gourmet roasts. Owner Yannis Taloumis opened the doors to Taf Coffee (a sit-down café) in 2009 and the family’s brand been going strong ever since, recently expanding to Taf Points, a mini-espresso bar concept in Athens and points beyond. The café, at the edge of the funky Exarchia district, is a haven for coffee aficionados interested in a wide variety of brews made by international-award-winning baristas. (Yes, traditional Greek coffee is still on offer.)

The ‘60s and ‘70s in San Francisco were synonymous with psychedelic “hobbies,” but tripping in the new millennium on Pier 39 is something you can now enjoy, legally, with the entire family. This labyrinth of 77 mirrors and black lights is reminiscent of a carnival fun house, and finding your way out of the 2,000-square-foot kaleidoscope of glowing twists and turns and befuddling dead-ends puts the fun in funky. While ‘80s music thumps, kids race through and into the walls, while adults feel their way down endless neon hallways. Created by Charles Magowan (who, no surprise, studied psychology at Yale), the Mirror Maze is a trip for all ages, and at just $5 it might be the cheapest one you’ll find in San Francisco.

Santa Monica has plenty of posh spots, but the best-known might be the Bungalow, a beach-bar-style lounge right across the street from the ocean. There’s a high-ceilinged main bar inside, but the real action happens on the front patio and in the back garden, where patrons can take full advantage of the pleasant L.A. weather. Patio seating is coveted space, but if you can snag one of the funky couches and wooden tables—especially if it’s by a fire pit—you can comfortably spend the rest of the night chatting over cocktails under twinkling lanterns, a cool ocean breeze at your back. A second location in Huntington Beach has vintage interiors and ocean views right on the Pacific Coast Highway.

This funky spot stands out among Amsterdam’s many urban “beach bars.” You can laze away a sunny afternoon at one of the picnic tables or chairs set up on a wide stretch of sand. Cocktails and beer slake your thirst, while decent pulled-pork tacos, burgers, and poke bowls keep hunger at bay. If the weather isn’t agreeable, the café—located inside a converted warehouse—strikes all the right hipster notes: Think distressed, graffitied concrete walls; leather sofas; vintage television sets; and groovy lighting. An adjacent warehouse hosts all sorts of events, from flea markets to film screenings to dance parties.

Built in the 1920s by a Croatian businessman, Palacio Astoreca underwent two years of refurbishment and restoration before opening its doors as a boutique hotel in 2012. The work was carried out to a meticulous degree, maintaining the original parquet floors, and adding splashes of color with art deco furniture and modern art, including one piece by Switzerland’s Frédéric Clot. The stucco-and-brick mansion rises up from the streets of Chile’s port city, Valparaíso, like a piece of red-and-white confectionary.

A statement staircase winds up to the 23 rooms, some of which have stand-alone bathtubs. And the basement level is home to a small spa with an open-air, wood-fueled hot tub set alongside a living wall. The reception level and entrance hall open out onto a terrace where lunch, tea, and cocktails are served, allowing guests prime views over the hilly city and Pacific Ocean. There are quiet corners for those seeking a solitary moment, including a library and a piano bar, which comes to life in the evenings with live music.

The gallery, boutique, and tearooms of Morocco’s most famous living artist, Hassan Hajjaj, is an essential stop for any art lovers staying in the city. Tucked away down a narrow alley behind the Rahba Lakdima (otherwise known as the Place des Épices), it’s like stumbling into a jewel box filled with pop-art treasures. Hajjaj made a name for himself with a series of photographs titled Kech Angels, which depicted local girls on mopeds dressed in eye-popping robes. The collection has been exhibited all over the world in such illustrious venues as the Victoria and Albert Museum in London and the Institut des Cultures d’Islam in Paris, but nowhere beats enjoying the work on home turf. While you’re there, treat yourself to his iconic recycled home and fashion pieces, such as a sardine-can lantern, a pair of babouches (Moroccan slippers) cut from a flour sack, or a stool from an oil drum. And if you hang around for a pot of mint tea in the courtyard, you might even meet the man himself.

Rock ’n’ Bowl is where to go to find sharps, flats, spares, and strikes all hanging out together. It’s a bit unclear whether this is a nightclub hiding out in a full-size bowling alley, or a bowling alley out enjoying a secret nightlife. Either way, it’s a very New Orleans destination, located near the upriver edge of the city. (It’s about a $15 cab ride from downtown.) After Katrina and a parting of the ways with his earlier landlord, the owner moved a few blocks down to this former paint store, installed new lanes, added a bigger stage, and hauled much of his original funky decor to the new spot. Check the website for forthcoming shows—there’s always plenty of space for dancing, which is especially fun during Thursday zydeco nights.

Why we love it: A boutique stay in Faubourg Marigny that’s full of history, character, and style

The Highlights:
- High design mixed with historic details
- A restaurant from a James Beard–nominated team
- Character-filled common spaces like the parlors and sun room

The Review:
Located in New Orleans’s culturally rich Faubourg Marigny neighborhood, the 71-room Hotel Peter and Paul comprises a historic church, rectory, schoolhouse, and convent, all built in the 19th century. When converting the site, local resident Nathalie Jordi and New York–based interior design firm ASH NYC took pains to preserve original features like cypress wood moldings, stained glass windows, and marble fireplaces, while adding signature details like antique chandeliers and custom rugs handmade in India. As a result, each guestroom has a personality all its own, evident in touches like canopy beds, Italian linens, and trays of locally sourced snacks.

That love for local eats extends to The Elysian Bar, where the team behind James Beard–nominated wine bar Bacchanal serves regionally focused fare like roasted Gulf shrimp and braised beef short ribs, and Sundae Best, which offers small-batch ice cream made with seasonal, locally sourced ingredients. Also on site is a cheery cafe for coffee and pastries; two grand parlors for reading the paper in a vintage rattan chair; a sun room modeled after Claude Monet’s Giverny home; an amber-hued bar serving low-proof spritzes for aperitivo hour; and a tranquil brick courtyard lined with palms, ferns, and vines. More impressive still is the decommissioned Catholic church, designed by famous New Orleans architect Henry Howard. Here, the hotel hosts a mix of private and public events, from weekly concerts to yoga and floral design classes.

One of the best places to feel the local side of Reykjavik life, the Kolaportid Flea Market is set in a spacious industrial warehouse close to the city’s old harbor. Open at weekends only, you can find anything from wool jumpers and vintage fashion garments to fermented fish and licorice, plus plenty of second-hand books and decorative knickknacks. Best to go early to avoid the crowds (it opens at 11 a.m.)—and best to have cash on you since many of the market’s vendors don’t accept credit cards.

Set on a picturesque terrace high above crashing waves, BijBlauw has breathtaking views and an effortlessly romantic vibe. The kitchen is partially open, so you can watch the chefs prepare fresh ingredients while you bask in the breeze. Try the truffle risotto, braised oyster blade steak, or “funky funchi,” a savory cornmeal mash with Parmesan cheese and a delicate poached egg. Want to make it extra special? Reserve a seat at the Chef’s Table, where you and your friends will get to sample the ever-evolving tasting menu, with wine pairings included. BijBlauw is a solid choice for breakfast, too—if you’re up early enough, grab a croissant and head for one of the coveted spots next to the water. Vegetarian options are available.