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Steps from the sand on Princess Margaret Beach, Jack’s Beach Bar is the perfect spot for an alfresco lunch, happy hour on the terrace, or both. It’s a good choice for dinner, too, although landside access is tricky, with lots of stairs and rough terrain that’s difficult to navigate in the dark. Whenever you come, look forward to local ingredients, prepared with an international touch. Pair the tropical quinoa salad with the catch of the day, or opt for the famous fried chicken, served with your choice of mango chutney, smoky barbecue sauce, blue cheese dip, or Mama’s Hot Sauce. If you’re having too much fun on the water, order something from the delivery menu and Jack’s will bring it directly to your boat—the restaurant delivers up to almost two miles from the beach.

Le Petit Hotel is housed in a former leather merchant’s building that dates back to 1867 and boasts original stonework arches and pillars at its entrance. Truly a “petit” hotel, its 28 rooms are spread across four floors and divided into S, M, L, and XL. Although it’s small, the hotel packs a stylish punch, mixing century-old exposed brickwork and stone with funky hardwood floors and modern-day luxuries—from free Wi-Fi and iPod docks to platform beds and multi-jet massage showers. In the guest rooms, splashes of bold, sunny orange and black accents create a contrast to the fresh white walls. Situated in the heart of Montreal’s fashionable Old Port area, guests are just steps from much of the city’s best shopping, dining, and art.

Puerto Princesa Underground River is set in a protected area of the St. Paul Mountain Range in Palawan. It’s a five-mile stretch of the Cabayugan River that runs through a huge limestone cave and directly into the West Philippine Sea near Sabang village (the bottom half of the river is tidal). Announced as one of the New7Wonders of Nature in 2012, it’s hard to fully envision unless you experience it for yourself. Reservations are required for the tours, which enter the underground river on a small boat. The boatman manually paddles you in as the light fades, the water becomes pitch-black, and you almost lose sight of the person beside you. The boatman will then start flashing his tiny light on the stalactites, stalagmites, and other rock formations you pass. The tour takes about 45 minutes and covers only a mile or so of the river (the inner portion is closed to the public).

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.

It’s quite a surprise to see a working chocolate factory in an airport, and Chitose Airport in Sapporo, Hokkaido, Japan, has one: the Royce’ Chocolate World. You can view the process from finish to end along the stretch of the terminal. They have recently renovated the terminal and it looks like a small amusement park. Aside from the chocolate factory, they even have a Doraemon Park. Royce’ was founded in Sapporo and they’re known for making very good quality chocolates. I first encountered Royce during a visit to Hong Kong, and I’ve always managed to bring some home. They’re popular in Asia. But since then, branches have also opened up back home in the Philippines. In fact, they have also very recently opened their 1st US store in New York and a second shop in Russia. My favorite is still their Classic Bitter Nama Chocolate made with dark chocolate. Each box comes with a small spatula used to lift each piece of chocolate from it’s casing. The chocolate pieces are also sprinkled with powdered chocolate on top. Aside from the usual milk chocolate and white chocolate flavors, they also have Maccha or Green Tea flavor. Their Nama chocolates are also available in chocolate liquor versions. Some other unique items included their chocolate covered potato chips or some with strawberry or lemon fillings.

This 1st-century wonder will take your breath away. Not only is it one of the city’s most ancient sites, it’s been in continuous use for centuries. Originally built as a private temple, today it is a Catholic church and the resting place of Italian kings and the artist Raphael. Make the most of a wet day in Rome and watch as the rain falls through the center oculus.

The most important historical site on Guadeloupe’s miniature archipelago of Les Saintes also boasts one of the most breathtaking views in the Caribbean. Perched some 400 feet above Les Saintes Bay, Fort Napoleon’s panoramic view of the water—dotted with sailboats and surrounded by bluffs—is worth a visit to Terre-de-Haut on its own. But it’s of historic interest as well. Rebuilt in the mid-19th century after the British destroyed it, the fort turned into a prison that was used during World War II. It was restored in the 1980s and houses a museum showcasing the history of Les Saintes. You can stroll inside to see the former grounds that served as a jail, and walk the botanical gardens afterwards, filled with the island’s various cactus species. Look out for iguanas peeking out of holes in the fort’s walls, as ubiquitous on the grounds as they are all over the island. Take in the glorious scenery for as long as you like before descending back down, on foot or on your rented electric scooter.

You can’t go wrong with any of the Intercontinental David’s rooms, all 555 of which look out onto the Mediterranean, but those seeking the ultimate view should at least consider the Jaffa Suite for its privileged perspective on Old Jaffa, or the Tel Aviv Suite, where the panorama includes Jaffa, Tel Aviv, and the sea. On the other hand, this hotel is so centrally located that you could simply walk to anything you want to see, from the evocative old city of Jaffa with its minarets, stone walls, and bobbing boats, to the Neve Tzedek district full of bohemian cafes and boutiques. Although you’ll be tempted to fill up on produce, halva, and pastries at the nearby Shuk HaCarmel market, save room for at least one dinner at the Intercontinental David—especially the traditional Shabbat meal that takes place in the third-floor Jaffa Court on Friday nights.

Though it sits squarely in Tel Aviv’s Lev Ha’ir (the heart of the city), Hotel Montefiore feels almost hidden away, not least because of the fact that greenery shrouds much of the restored 1922 mansion. Gaze out the window of the lobby restaurant (where you should, without fail, order the Tunisian eggs for breakfast) and you’re as likely to find yourself leaf-peeping as people-watching. The hotel feels all the more intimate with its grand total of 12 guestrooms, each cozily appointed with well-stocked book shelves and retro armchairs. The vibe here isn’t strictly old-timey, however. You’ll also find a striking modern art collection and a DVD library that (almost) rivals the book selection. As tempted as you may be to binge-watch or read in your down-draped bed, don’t skip a nightcap in the downstairs bar, which is the picture of international style, whether you’re talking about the crowd or the menu offerings.

It’s hard not to feel hip upon entering this Williamsburg hotel. Credit those Insta-cool vibes to the always abuzz rooftop lounge Westlight, or to Leuca, where food-loving socialites flock for a taste of the Italian plates that chef Andrew Carmellini does best. Thanks to the hotel’s partnership with Brooklyn Arts Council, locally designed artworks greet guests in each of the 183 rooms, as do luxe Frette linens, floor-to-ceiling windows, and wraparound balconies with stellar views of the Manhattan skyline. Once settled in, it’s straightaway to the pool, a 60-foot stretch of water surrounded by daybeds and cabanas. If you’d prefer a private hot tub, book the Vale Garden Residence, a two-story suite complete with an open-air Jacuzzi, a fully furnished patio, and its own covetable city vistas.

The cathedral in Amalfi, with its glittering gold mosaic facade and colorful Majorca-tiled dome, dominates the main piazza. Construction on the cathedral began in the 9th century, and centuries of additions and renovations are revealed in the mashup of Moorish and Norman Romanesque styles present. Climb the 62 steep steps in front to admire the enormous bronze doors that were cast in 11th-century Constantinople. Inside, the crypt holds the relics of St. Andrew the Apostle, the patron saint of Amalfi. Through the cathedral’s portico, you can enter the Cloisters of Paradise, a 12th-century arcade bordered by 120 columns surrounding a garden. This peaceful space was created as a burial place for the noble families of Amalfi.

Located near Dundee’s now-thriving waterfront, the Michelin-starred Castlehill Restaurant serves sophisticated Scottish cuisine made with locally sourced ingredients. In the elegant dining room, guests enjoy a seasonally changing menu of modern dishes, like Scrabster hake with roasted garlic purée, and pork belly with chorizo, butternut squash, and crispy monkfish cheek. A wine list curated by specialist merchants rounds out the offerings, providing the perfect complement to Scotland’s natural larder.

With soaking tubs and smart TVs in every room, Hotel Ivy is sleek and sophisticated. In addition to the stylish rooms, the subterranean cocktail bar (Constantine) and coastal Italian restaurant (Monello) are hip destinations in themselves, with renowned local chefs and bartenders from Borough and Parlour at the helm.

Built in 1863, Magnolia New Orleans is classic in decor—especially in the marbled lobby with its antique furnishings and Renaissance murals—but with all the up-to-date amenities you’d expect: Rooms and suites have flat-screen televisions and Nespresso coffeemakers, and there’s a small but well-equipped gym on-site and a rooftop sundeck with a Jacuzzi.

Jennifer MacKay’s clothing boutique is the go-to store for fashionable locals, who know they’ll find pieces exclusively in her shop. I have a weakness for the shoes. (604) 685-8885. As told to Rhonda May. This appeared in the September, 2012 issue.