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No visit to Ambergris Caye is complete without an afternoon at the Palapa Bar. Situated at the end of a dock surrounded by turquoise waters and cool breezes, Palapa Bar attracts a mix of locals, travelers, and some of the coolest bartenders on the island. On a warm day, eschew the barstools and opt instead to float in inner tubes beside the dock; you can even have cold buckets of Belize’s Belikin beers lowered down to you. In addition to beer and standard cocktails, fun creations like Scotty’s Palapa Punch (three different types of rum, triple sec, mango, pineapple, and a squeeze of lime) offer some island-inspired refreshment. Up in the palapa, recommended items from the menu include sausage dip, pulled pork sandwiches, and the immense half-pound burger. Palapa Bar is 1.5 miles north of town and easily reached by golf cart, taxi, bicycle, or water taxi, which drops you right off at the dock.

This stunning white-sand stretch, just a five-minute drive east of Port Antonio, is the only beach in Jamaica with waves high enough to surf. Boston Bay is also one of the few remaining public strands on the island. It continues to attract more locals than tourists and as such is nearly vendor-free. You can watch kids splashing about on their boards, or you can rent your own for a Surfing 101 lesson. Be forewarned: As at many beaches, sometimes the waves are flat, but you can console yourself with a short stroll down the beach to the famous Boston Bay jerk chicken stands.

One of the great things about the Caribbean is that its rich history was often written at beautiful, easily accessible locations. One of the best places to learn a bit of that history is pictured above. That’s the beach at Columbus Landing in my home island of St. Croix. It was here, in 1493, that Columbus sent ashore a small contingent of his men to scout for fresh water. What they found instead were a group of Indians who weren’t too keen on visitors. What’s the whole story of Columbus and his less than stellar (to say the least) track record throughout the region? That may take a bit more book learning, but feeling what these new visitors may have felt coming ashore in this corner of paradise starts on these sands.

After Carcassonne in southwest France, Visby lays claim to the most important and best-preserved medieval city walls in all of Europe. The town’s citizens began building the original six-meter-high (20-foot) fortified walls in the 13th century, and they eventually grew to over 11 meters (36 feet). Today, the wall still stretches for 3.4 kilometers (2.1 miles). Walk in its shadow and explore the 36 intact medieval towers as well as numerous gateways. The North Gate offers the most impressive view of the wall, providing a sense of its enormous scale. St. Mary’s Cathedral, a few blocks inland, also dates to the 13th century.

Perched on a not-so-lonely nude beach on the northern end of Sauvie Island is an enigma. Well above waterline lies a 30-foot orb that piques the imagination and challenges explanation. The “spaceship” origin is not interstellar but certainly presents itself as other-worldly. The craft is actually a ferro cement experimental boat built around 1970 just upriver. It was designed as a self-righting sailboat and carried a local family on adventures for a couple decades before it got away. Now covered in moss and graffiti, it sits as a testament to Oregon innovation and exploration. To do some of your own exploring of this mysterious craft, take Reeder Rd out to where the pavement ends at a spot called Collins Beach, aka the nude beach. (Yes, if you venture out in summer, you will see naked people.) There’s a parking area (permit required) and trails down to the beach. Sitting up in the trees, just above the sand, sits the stripped-out hulk of a dream. The tri-hulled beast looks more like a lifeboat than a spaceship, but alien nonetheless. Be careful climbing around if you decide to explore inside. The rusting steel framework is losing its cement skin in places and can be dangerous. Cycling to the site is a great way to spend an afternoon on the island and get a great workout in the process.

Ontario has another wine destination, Prince Edward County, affectionately named “The County.” This cluster of towns, about 2.5 hours east of Toronto, is home to some of Ontario’s best wineries. But never was there a great place to stay until summer 2015 when Jeff Stober, the hotelier behind Toronto’s stylish Drake Hotel, opened a rural clone, the Drake Devonshire. It’s the ideal retreat for travelers wanting their Drake by Lake Ontario. Once a 19^th-century foundry, the building is now a contemporary farmhouse-cottage, decked out with 11 individually-designed hotel rooms and two suites in the quaint town of Wellington. The property offers coziness all year round in the communal living room and out back over a lakeside fire pit and s’mores. Guests can hang in the barnlike Pavilion for musical performances, sommelier seminars, seasonal events, or just to gawk at the floor-to-ceiling mural by Brooklyn artist FAILE. It doesn’t hurt that Sandbanks Provincial Park—known for its 60-foot sand dunes—is practically the backyard of the Drake Dev.

Bar Raval looks ordinary from the outside, but inside, the sinuous lines of the floor-to-ceiling mahogany woodwork—bar, walls, window frames—instantly bring Gaudí to mind. Created to mimic the spirit of Barcelona’s pintxos bars (in addition to the Catalonian influence of the decor, platters of food are laid out on the bar, as is the Basque pintxos tradition), the space is often packed. In the mornings, patrons sip lattes and enjoy doughnuts finished with a lick of chocolate and spiced hazelnut.

Suddenly, grub that is both Chinese and Jamaican is a thing. Chef Craig Wong, third generation Chinese-Jamaican himself, has taken over a Dundas West space and done quite the number on the local dining scene, turning out a cuisine of his own that manages to encapsulate all that is Toronto. Pick from eats like the Jamaican patty double down — chef’s take on the famed KFC number — and the dirty fried rice with red sausage and peas. For a small group, go with the so-called Whole Shebang and test out Wong’s take on jerk chicken. Dinner can be reserved, but if you’s aiming for brunch, be there when the place opens and tuck into the Hong Kong-style waffles and the luscious maple butter French toast.

Montreal’s very own Prince of Darkness is best known for his mastery of soft, buttery black leather and his play with textures and details such as zippers and horse hair, but he’s expanded his recent collections into a less gothic and more widely accessible styles that have even branched out into color ¬– albeit dark browns and blues. The women’s wear designer has created collections for off-the-rack store Bedo, but to get a real sense of his unique vision and approach to form, best head down to his sleek boutique on chic Rue Saint-Paul in Old Montreal. Here you’ll find statement pieces to be worn to your next gala as well as rugged wear you can integrate into your everyday.

Almost unchanged since 1912, the Théâtre Corona (Corona Theatre) in Little Burgundy was built to host showings of silent films accompanied by live music and comedy shows by local troupes. You can still find an orchestra pit and the original dressing rooms under the stage, but since the late 1990s—after coming close to demolition—it has served mainly to host live music, by acts like Buck65, La Roux, and Arcade Fire. The heritage décor, with painted ceiling, gilded columns and heavy jacquard brocade curtains, and the relatively small capacity for 700 spectators, make this a singularly intimate place to see a show. The best sightlines are from the balcony, but there’s nothing like the feel of a smooth wooden dance floor beneath your soles.

Wilensky’s is sort of an institution in the Mile End. Family-owned since its opening in 1932, the place is famous for its extremely cheap snacks, no-nonsense approach, and retro decor. Pressed tin ceiling, Kik Cola clock, ring-up cash register, old-fashioned soda fountain—this place sometimes feels like a time warp or, at the very least, a museum. Perhaps what makes Wilensky’s so special is, incidentally, the Special ($3.90): “All-beef salami with all-beef baloney grilled to mouth-watering perfection on a tasty roll with a hint of mustard.” But don’t try to change anything in it—the owner, Ruth, will not have it. The Special is what it is, and no amount of money will make Ruth change it. Hell, she even wrote a poem about it: When ordering a Special, you should know a thing or two. It is always served with mustard; it is never cut in two. Don’t ask us why; just understand that this is nothing new. This is the way that it’s been done since 1932. Amen to that.

L’Express, on rue St-Denis in the Plateau Mont-Royal neighborhood, opened in 1980 and has about it the air of a beloved institution. Indeed, with its timeless style, it feels even older than it is. This popular spot serves classic renditions of bistro fare—steak tartare, bone marrow, onion soup—into the early morning hours (2 a.m. except for Sundays, when it closes at 1 a.m.). When the kitchen ventures into new territory, the results are impressive. The spaghetti with mushrooms is unconventional in its presentation (topped with a healthy serving of arugula)—one of those dishes you try on the road and then want to re-create at home. Reservations recommended.

Rustic elegance is the order of the day at La Champagnerie, a champagne-only bar in Old Montreal. Between the delicious cocktails, heaven-sent food, and exposed brick walls of this historic building, the drinking experience will be memorable. The menu features over 50 different brands of bubbly (including real champagne, cava, and prosecco) and a very entertaining sabering act, as well as brie poutine and oysters. Contrary to popular belief, la Champagnerie isn’t that expensive. Yes, there is the odd $500+ bottle, but visitors can easily enjoy a meal and a cocktail or two without needing to remortgage their house. A very nice way to spend an evening, if you ask me—champagne, Old Montreal, and good music. Santé!

Ask any Montrealer the question “Which is the fanciest restaurant in town?” and chances are Toqué! will be a frequent answer. Indeed, quite fancy. But also quite expensive. Luckily, chef Charles-Antoine Crête, once mentored by Toqué’s Normand Laprise, decided that a more accessible and younger version of the famous restaurant would fit perfectly well with the new Place des Festivals—in style, location, and ambience. And he wasn’t wrong. I always go for the beef tartare, and not once have I been disappointed. The menu changes according to the season, but there is a constancy in quality, regardless of the time of the year. This is definitely the best way to get a taste of Montreal‘s finest, sans the waiting list and the steep check.

This 26-meter-tall (85-foot-tall) colonial monument that looks out over Mumbai Harbour is one of the city’s best-known landmarks. Built by the British as a triumphal arch to commemorate the 1911 visit of King George V to what was then called Bombay, it was also the site from where British troops in 1948 left India as the country achieved independence. Today, it’s a fun spot to hang out and people-watch before catching a boat to Elephanta Island.