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A classic New England bed and breakfast with a boutique hotel vibe, the Union Street Inn is housed in an impeccably maintained 1770 whaling captain’s home just off Main Street in downtown Nantucket. A short walk from the Hy-Line ferry and harbor, the inn has a convenient location in town (including parking, a huge perk on the island) and can also outfit guests with beach gear for a day on the sand. A quintessential gray-shingled exterior contrasts with the bright blue chinoiserie patterns and crisp white Frette and Matouk linens in the inn’s 12 immaculate rooms. Union Street’s cherry on top is the made-to-order gourmet breakfast, which might feature fresh peach cinnamon rolls or homemade carrot cake, depending on the season.

Beyond the crowds of central SoHo—in a formerly industrial nook with historic roots on the edge of the Hudson River—a neighborhood is emerging: Hudson Square. This is the home of Hotel Hugo, a stylish loft-inspired retreat with an Italian spirit that has brought a bit of European-inflected flair to the neighborhood. This extension of SoHo has long been known by New Yorkers for its nightclubs, restaurants frequented by locals, and of course, the gorgeous Hudson River Park, an uninterrupted promenade that stretches the length of Manhattan. Now it has a chic hotel, complete with a rooftop that has a Cuban cantina vibe that serves cocktails against a backdrop of the Hudson River.

North Florida’s beaches hardly get the attention of those farther south or on the Gulf of Mexico. But there’s a lot to love about this laid-back surf community just north of St. Augustine’s busy historic district. The beach’s steep drop-off makes little waves jack up nicely, so Vilano is a favorite with surfers—especially on the incoming tide, when the waves are best. And Porpoise Point, on the southern end of the beach, is a great place to cast a line into the surf and fish. Facilities at the beach include parking, showers, pavilions that can be rented for gatherings, and picnic areas.

On Jean-Talon near Parc Avenue in the rapidly gentrifying neighborhood between Mile End and Park Ex known as Mile Ex, Bar Le Ritz PDB is a large open space with a few tables by the big front windows (always open in summer afternoons so that the fun spills out into the street) and a warm, relaxed atmosphere. It’s better known as a show-bar than a hangout bar, though that is slowly changing with expanded opening hours and a wider range of drink options. Like most Montreal music clubs, anyone can reserve a spot to play here; but the average night tends to lean towards indie rock, post-punk, alternative pop sounds.

Stretching high above Fifth Avenue, the Peninsula is a glamorous, classic hotel. Formerly the Gotham Hotel (built in 1905), this building is at the heart of prestigious Midtown Manhattan with neighbors like the Museum of Modern Art and Rockefeller Center. It has a convenient location for Fifth Avenue shopping and exploring Central Park. The Peninsula is a favorite of New Yorkers for its rooftop bar, Salon de Ning, with its mesmerizing views of the city skyline. Rooms are polished and inviting, designed to resemble a luxurious New York City apartment. Kick off your stay with a classic cocktail in the Gotham Lounge, followed by a locally sourced meal at the elegant Clement Restaurant and Bar.

Mole Creek Karst National Park, along with the surrounding Tasmanian Wilderness World Heritage Area, offers subterranean streams and pools, plus at least 300 caves. At Marakoopa Cave, you’ll feel as though you’re in mother nature’s planetarium—the walls are lit up by Australia’s largest colony of glowworms. Caves like Honeycomb and Westmorland are best explored during a half- or full-day trip with Deb from Wild Cave Tours. Unlike most guides, she holds a PhD in speleology. But if one day is not enough, make it a wild caving weekend to progress from walking and wading to scrambling and squeezing through tight crevices. Local beer and wine await you at Mole Creek Guesthouse.

Once summer has arrived in all her glory, city folk yearn to escape the concrete jungle. The cheap and chic solution for locals is to pack a picnic and head for a beach day on the Toronto Islands, just a short ferry ride away. Of the three primary islands, all of which are connected by paths and bridges, Centre Island boasts the highest number of visitors; people head straight to its main strip to get to the beach and the amusement park. Ward’s Island offers more charm: In addition to the sandy shore, there are small summer cottages and gardens. Those intent on exercise can rent bicycles or paddleboats.

Hout Bay is basically Eden. This ecological utopia has everything a nature lover could want, from imposing mountains and miraculous views (check out the Twelve Apostles range) to World of Birds, the largest bird park in Africa, home to 3,000 birds and over 100 walk-through aviaries. On weekends, you can shop for food and crafts at the lively market at the end of the harbor road. Besides Chapman’s Peak Drive, there are two other roads into Hout Bay, one from Constantia and another that passes the gorgeous surfer beach of Llandudno—also the exit for Sandy Bay, a nudist beach.

Situated on the northern end of Delaware Park, the Buffalo Zoo offers family-friendly fun for warm summer days. Built in 1975, it’s the third-oldest zoo in the country, but the facilities have been updated over the years to provide spacious habitats for the resident animals. The underground sea lion exhibit and Rainforest Falls are favorites, as they allow visitors to get close—but not too close—to the animals. Also be sure to catch a glimpse of the giraffes enjoying the sunshine from their street-side enclosure. To avoid crowds, arrive early in the day—the place can get packed, especially on nice days.

The most rugged, sketchy roads always seem to lead to the best surf breaks. This photo captures the early morning drive over the hill to Cerritos beach in Baja Mexico. Down below I discovered perfect, glassy rights and only a few early risers in the water. In the distance at the point is Hacienda Cerritos, a boutique hotel from which you can stumble out of bed and down to the surf. Mario Beceril, a Baja native, runs a great surf school from the beach for anyone who needs a lesson. mariosurfschool.com

Most people travel to Canada in the winter to ski the famous big resorts like Whistler and Lake Louise. But 20 minutes from downtown Banff is a little “hill"—as the Canadians like to call their mountains—called Sunshine Village. The resort, located on the continental divide of the Canadian Rockies, spans more than 3,300 acres and has three mountains to explore. I visited in mid-March (locals say March conditions are often best) and we had perfect powder. The resort stays open through late May for those looking to extend their ski season. The ski-in, ski-out Sunshine Mountain Lodge is a perfect base for those who want to get first chair in the morning. Rooms have great views of the surrounding mountains and loft-style rooms with Murphy beds are perfect for couples or families. I liked the lodge’s unique offerings such as hot tub bingo night and new yoga and ski retreats. The mountain has terrain for all levels. Serious skiers and riders will want to go off-piste and experience Delirium Dive. A check-in gate ensures skiers and riders are equipped with a beacon and safety gear before they tackle the Dive. On Lookout Mountain, you’re likely to find powder stashes on some of the steep tree runs such as Little Angel, and Horot’s Revenge. And don’t miss the frozen waterfall on the way down the Waterfall run off the Wawa chair.

Foodies from all over flock to Mama’s Fish House for ocean-to-plate dishes in a postcard-perfect setting. At this tiki bar meets restaurant, the fish is delivered daily by local anglers and many dishes showcase regional ingredients like Maui onions, Hawaiian chili pepper, and Hana ginger. As a young couple in California, owners Floyd and Doris Christenson fell in love with Maui while on vacation. In 1960, they sailed back across the Pacific, navigating only by sun and sextant, and anchored back on their dream island, where they eventually opened Mama’s. Today, the hot spot can be crowded and pricey, but few begrudge the premium for the fresh fare and stunning panoramas. Make a reservation well in advance for an ocean-view table.

Consisting of 25 domes, EcoCamp was inspired by the round houses of ancient tribes that formerly inhabited the area now known as Torres del Paine National Park. There are three categories of domes, all made from green plastic with sheer windows. Standard domes feature twin or double beds and a shared, campsite-style bathroom. Standard domes don’t have central heating and can be nippy in the Patagonian climate. Superior domes have gas heaters and en suite bathrooms. The suite domes are similar to the superior rooms, but have wood-burning stoves (and the suite dome loft has two floors). Domes are connected by raised wooden walkways for minimal environmental impact. Communal meals and pre-excursion briefings take place in the central community dome.

One of Dalmatia’s most underrated cities, Šibenik is finally being recognized as an exciting coastal destination. Its medieval heart is a stone maze of steep alleyways dotted with charming squares and hidden cul-de-sacs, not to mention a pretty harbor and a seafront promenade lined with cafés. Crowning it all is the Cathedral of St. James, an architectural masterpiece incorporating style elements of both the Gothic and the Renaissance. The cathedral is said to be the world’s largest church built entirely of stone—most of which was quarried in the nearby Adriatic islands. Of particular note in this UNESCO World Heritage site: the frieze of 71 heads on the cathedral’s outer wall, which depicts 15th-century citizens of Šibenik with many different moods and personalities.

Most people in the city know The Battery as an exclusive social club, but did you know it also houses a 14-suite, boutique hotel, open to members and non-members alike? Featuring a maximalist decor that channels the many sides of San Francisco—be it Chinatown inspired motifs on the curtains or beams from the old ships that used to dock in this location (this area was once water)—the hotel will remind you where you are at every twist and turn. Rooms are spacious, comfortable, and impeccably designed.