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  • 5/red Piazza Santo Spirito, Florence, Italy
    When the sun sets, Piazza Santo Spirito wakes up and the large square fills with college students and young professionals. Volume is where they gather for strong cocktails and live music. Located in the former workshop of Alfonso Bini, a woodworker who specialized in carved hat forms and later more-creative pieces, the space retains the warm vibe of the local craft studios. Small tables and chairs are set up alongside shelves crowded with books, tools, and art. Seating outside affords a view of the after-dark action on the piazza as well as the striking Santo Spirito church.
  • Set on a hill some 2,000 feet above Papeete, with impossible views of the sea and Moorea beyond, O Belvédère is the place locals take visitors for thrilling sunsets and good food. The restaurant and bar have the air of a tree house—the outdoor terrace is even built around the trunk of a tree. An inviting swimming pool on the hill below and occasional live music add to the already strong appeal. Arrange for a 5 p.m. pickup from your hotel to reach the restaurant in time for a celebratory sundown cocktail. The fondue is highly recommended.
  • 31740 Mulholland Hwy, Malibu, CA 90265, USA
    Wind through the Santa Monica Mountains to Malibu Wines, a grassy garden retreat with gorgeous views for picnicking and sipping wine with friends. The space is accented by Instagrammable features like the metal WINE sculpture that emulates the iconic LOVE sculptures by artist Robert Indiana that are found in cities around the world. Entry is free; just order wine from the farmhouse-style tasting room and enjoy the live music and festive atmosphere on the weekends. (Weekdays are more mellow.) Table reservations, including one inside a vintage school bus, are recommended for groups—but if you’re more flexible, simply bring a blanket and some food, find a spot to spread out on the lawn, and explore the grounds.
  • 5110 San Fernando Road
    The building that houses Moonlight Rollerway dates back to the ‘40s, when it produced airplane parts for World War II. In 1956, it was repurposed as Harry’s Roller Rink, and the current iteration maintains the original’s 2¼-inch-thick maple flooring—laid out without nails, secured by tongue and groove joints. The 1950s vibes are still alive and well, and the space has been a setting for many TV shows, movies, and music videos—you might recognize it from appearances in episodes of Glee and Modern Family. The owner, Dominic Cangelosi, started working at the roller rink in the late ‘60s before buying the place in 1985, and he still plays the organ for spinning patrons every Tuesday night.
  • Cunucu Abao 37, Noord, Aruba
    This spot near Eagle Beach is pure Caribbean. The live music is infectious, the plates come piled high, and the tables are situated outdoors, under the sky or a tin-roof overhang. Plus, there are more local patrons than visitors. While the atmosphere is laid-back, the menu is full of sophisticated presentations, from island favorites to international dishes. Popular picks include the crab cakes, almond-dusted grouper, and lobster ravioli. The wine list is also excellent, as is the craft beer selection. Note: Reservations are recommended. The restaurant is closed on Sundays.
  • Highway 93 North, Alberta, Canada
    This five-kilometer (3.1-mile) hike starts at Bow Lake, directly in front of the legendary, red-roofed Num-Ti-Jah Lodge. The turquoise waters and historic stone-and-log structure make for great photo ops before you even get on the trail. Then, the path winds around the lake before climbing across a series of moraines left behind as the Bow Glacier has receded—the lunar terrain will make you feel like you’ve landed on the moon! The trail eventually ends at the Bow Glacier Falls, dropping vertically from the rock face towering above. With only a 155-meter (510-feet) elevation gain, this hike offers an amazing payoff for little effort, though footing can be challenging on rocky sections with some loose rock.
  • 26 Via Axel Munthe
    Walk the long shop-lined Via Capodimonte (or, if you are feeling particularly industrious, climb the 921 Phoenician Steps to the very top) to reach the former home of the Swedish physician and author Axel Munthe. This 20th-century mansion, now a museum with magnificent gardens, sits almost 1000 feet above the sea and offers unbelievable views over Capri and toward Naples and Mount Vesuvius. During your visit, follow tradition and make a wish with your left hand touching the ancient Egyptian sphinx statue. There is a café at the top of the gardens and occasional live music on summer evenings.
  • Is this polished industrial space, in an odd corner of the Centro, the thinking man’s disco? Organizers prefer to speak in terms of a cultural center, and the installation’s multiple spaces are venues for everything from literary events and screenings to a dynamic agenda of live-music performances. But it’s the DJs and dancing that are bringing in crowds, crowds that are alternative and low-key, creative, sex-pref-neutral, and seemingly little impressed that their hangout has become so fabulous. Priced-to-move libations and overall edginess keep the crowd skewing young; the space’s various environments add variety to your night out—and sometimes there’s even a place where you can chat (or canoodle) without screaming.
  • Rum Point, Cayman Islands
    Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.
  • Hoàn Kiếm Lake, Hang Trong, Hoàn Kiếm, Hanoi, Vietnam
    A couple of blocks west of the Sofitel Legend Metropole Hanoi, Hoan Kiem Lake—meaning Lake of the Restored Sword—is one of Hanoi’s anchors. It contains a number of sites worth visiting, like Ngoc Soc Temple and the picturesque, red-lacquered Huc Bridge. The greatest fun here is people watching, from men and women jogging round the perimeter to retired folks doing tai chi or dancing. Many locals come to socialize or just take a few moments to escape the city’s chaotic roads and traffic. Visit in the morning as the city is waking up and the air remains blissfully cool. Photo by Binder.donedat/Flickr.
  • Princess Drive The Bight Settlement, The Bight Settlement TKCA 1ZZ, Turks and Caicos Islands
    Newlyweds looking for a luxury boutique villa style hotel experience will dig the Somerset, which has just 53 rooms spread over eight buildings right on Grace Bay Beach (walking distance to DIY snorkeling). A sort of hotel/villa hybrid, digs are in multi-room suites with fully equipped kitchens. It works great for families, especially as dining out in Provo adds up quickly. Beyond the rooms, there is a 70-foot infinity pool to chill by as well as a lengthy list of activities that will keep the kids busy while you do so. A spa and two restaurants -- one casual, the other more formal -- complete the picture. Oh, and on Monday nights, the property’s general manager hosts a cocktail hour with free drinks, tapas, and live music for guests. Tuesday nights are dedicated to BBQs on the beach. The villa resort also works well for couples, as the suites here are beyond spacious and very private and there are a few different swimming pool options.
  • 57 Kolokotroni
    Booze Cooperativa is “a brain hub of tribes and nations in creative disruption.” That certainly sounds like millennial trendspeak, but the Cooperativa—a three-story neoclassical textile mill repurposed in 1989 into spaces for art, music, and people-meeting, and eating and drinking, has been promoting local artists, providing community for artists of all sorts (many of whom co-work, or play chess with their friends, at the six-meter-long—almost 20 feet—table by day), and acting as a nighttime watering hole ever since. Booze isn’t just about booze at all, but you can smoke here—its owner registered the building as a political party headquarters to get around the Greek indoor smoking ban.
  • 80 Asilomar Avenue
    Standing its ground between a cypress grove and the Pacific Ocean, the Point Pinos Lighthouse is the oldest lighthouse in continuous operation on the U.S. West Coast—and one of seven lighthouses for which Congress appropriated funding shortly after California statehood was ratified. But this lighthouse wasn’t just an aid to navigation; it was also a social hub in early Pacific Grove. Robert Louis Stevenson wrote about lighthouse keeper Allen Luce and his piano playing, while a fondness for entertaining inspired locals to call keeper Emily Fish the Socialite Keeper. The lighthouse beacon, a third-order Fresnel lens, has flashed nightly since 1855 and is still used in the tower today—the light is visible up to 17 nautical miles out to sea. Docents are on duty to answer questions as you tour the lighthouse, from the 1890s-style parlor to the 1920s-style kitchen, and up to the Emily Fish bedroom and lookout. Right behind the lighthouse is the El Carmelo Cemetery, one of the most peaceful seaside cemeteries, with deer wandering through to nibble on the grass.
  • Southwest of Anguilla is one of the island’s top three beach areas: the two-mile-long brilliantly white stretch at Rendezvous Bay. Its long shore, steady breeze, and calm Caribbean waters provide a break from the crowds at Shoal Bay and Sandy Ground. The western end does offer some fun daytime beach-bar action, which grows rowdier at night and on the weekends, when the famous Bankie Banx’s Dune Preserve venue attracts residents and visitors for live music. You can view St. Martin, across the channel, from shore.
  • Jalan Gereja, Bandar Hilir, 75000 Melaka, Malaysia
    Malacca was under Dutch rule from 1641 to 1795 and then again from 1818 to 1825, and the buildings along Dutch Square reflect this history, all painted in terra cotta—the square is also often called Red Square, because of the color of the buildings that sit on it. Just behind the square’s clock tower, the Stadthuys was built in 1650 as Malacca’s city hall; it continued to serve this purpose even after the British took control of Malacca. It’s believed to be the oldest Dutch building in Southeast Asia. The large but simple building has white wooden shutters and a tiled roof. Today, the Stadthuys houses several museums, including the History and Ethnography Museum.