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Running for more than eight miles through the southwest part of the island of Montréal, the Lachine Canal is a window onto the city’s industrial history, reborn in recent decades as a place where nature and the city meet. Originally opened in 1825, the canal, with its five locks, allowed ships traveling between the upper St. Lawrence River and the sea to avoid the treacherous Lachine Falls. (Before the canal opened, ships would typically off-load their cargo at the village of Lachine, which would then be loaded onto another ship on the other side of the falls.) The canal’s banks would soon be filled with small factories, but by 1950 the area had started to decline, in part due to the success of the railway. In 1970, it was closed to shipping completely. Recent efforts to clean up the canal have been successful, and now bikers and walkers take advantage of the paths that line it, while many of the former factories and warehouses have been converted into luxury lofts and condos. In 2002, the canal was opened to boats again—pleasure crafts, not barges—that travel its length. If you decide to explore the canal, the Atwater Market was one of the early projects to redevelop the area, and it remains a great place to buy all the items needed for a picnic.

Built in the Roaring Twenties, the Royal Hawaiian ushered in the glam age of Waikiki Beach. The so-called Pink Palace, a Spanish Moorish–style confection set on bright-green lawns was, at the time, the priciest hotel project in the Pacific and a fast favorite of Hollywood royalty and East Coast blue bloods (who, in those early years, arrived by steamship, along with their piles of trunks and chauffeured cars). For those first few decades, anyone who was anyone, it seemed, stayed at the Royal Hawaiian; on any given day, you might see the likes of Spencer Tracy autographing a coconut or Joe DiMaggio surfing off the hotel’s beach. Once other luxury hotels sprouted up on Oahu, the Royal Hawaiian’s star faded some, but after a massive renovation in 2008, it became a member of Starwood’s Luxury Hotel Collection and, once again, one of the top spots on the island. The makeover managed to keep those graceful old bones and art deco flourishes (miles of tile, sweeping arches), while giving the whole place a long overdue upgrade. Genteel surroundings aside, the hotel is as lively as ever. But at night, when the oceanfront Mai Tar bar is rocking, guests can still scope out quiet corners. Retreat to the gracious portico lined with rocking chairs or the garden pathways dreamily lit by torches, and you’ll discover that the romance of old Waikiki lives on.

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.

The Old Town’s main street, Stradun, also known as Placa, can’t be missed—it’s the biggest and widest of all the thoroughfares, and you will probably walk it several times during your stay here. It’s especially nice in the late afternoon, when the angle of the sun makes the pavement shine and the swallows soar overhead. Continue down to the old port and along the waterfront to the far end. Porporela Pier, built courtesy of the Austrian administration’s rule in Dubrovnik during the 19th century, is today somewhat of a lovers’ rendezvous. After your stroll, the benches along the pier provide a simple relaxing moment to take in the views of Lokrum island and Cavtat in the distance.

If you find yourself on Middle Caicos, don’t miss one of the most dramatic shorelines on the islands, along Mudjin Harbor. The three-mile-long stretch has tall limestone cliffs that drop directly into the water, interspersed by sandy coves. The ocean here is often too rough for swimming or snorkeling, but there are excellent walking trails, including the historic Crossing Place Trail that provides great views of the coastline. Mudjin Harbor also has two large sea caves that you can explore from the beach.

A favorite among Hollywood royalty, the Big Island’s Four Seasons is more secluded than its sister property on Maui. It sits on 863 acres of palm-fringed coastline, with little else for miles in any direction, other than two exclusive golf courses and some of the most expensive vacation homes in the state. Yet, conveniently, the hotel is only a 15-minute drive from Kona International Airport, and it isn’t uncommon for guests to fly in, park themselves at the resort, and never leave. Why would they? It’s an immaculate, ingenious playground, shamelessly verdant against the area’s prodigious black lava. There are seven pools to choose from, including one rock-walled rectangle in the ocean, and another man-made lagoon stocked with thousands of reef fish for guaranteed snorkeling success. Kids can camp overnight in a rock amphitheater. Lovebirds can have candlelit dinners on the beach. Even the accommodations are a Polynesian fantasy, with tropical woods and large headboards. All that, along with a tiki torch–lit beachfront, a French head chef, a swank sushi bar, a staff that treats every guest like Hollywood royalty, and honest-to-goodness cultural cred (the on-site museum and cultural center are well worth visiting), and it’s easy to understand why one would happily pay a king’s ransom to spend a few days here.

A combination of train and bus, this three-hour tour weaves a fascinating route past some of the island’s most historic sights. Constructed from 1912 to 1926, the rail system originally carried sugar from St. Kitts’ estates to the factory in Basseterre, but today serves as a fun tourist attraction. Visitors ride in double-decker cars—the lower is air-conditioned, the upper open-air—past black-sand beaches, old plantations, and sugarcane fields, and then up a portion of Mount Liamuiga.

December in Stockholm is a great time to explore various Christmas markets (Julmarknader) around town. At Stortorget in Gamla stan (Old town), you’ll find the city’s most popular Christmas market where you can pick up a variety of porcelain ornaments, festive decorations, and wooden gnomes as well as dig into gingerbread cookies (pepparkakor), mulled wine (glögg), candied almonds, jams, and deli meats.

the Stockholm city hall building went up in the 1920s and has a variety of styles incorporated into it. Its possible to take a guided tour around the building and admire the architecture, especially the gold room which is made up of millions of mosaics. This is also the building where Nobel Prize winners party with the king of Sweden.

Stretched out from the northwest corner of the island like a small arm, Pigeon Island is a historical landmark and a satisfying all-in-one nature, beach, and hiking escape minutes from Rodney Bay Marina. The 44-acre mountainous green plot is home to the preserved ruins of British military forts and garrisons; the Brits chased the Caribs out and used the islet to monitor French activity. Walk among the ruins, and hike up to the cannons of Fort Rodney, where the lookout point offers a breathtaking panoramic view of St. Lucia’s coastline and the sea below, dotted with sailboats. Hike down to the beach for a swim and a toast to history at Jambe de Bois, a restaurant on the water.

As a rule, Bermuda’s sense of sophistication includes a certain level of old-school formality. With the opening of this namesake eatery from the internationally renowned and somewhat hipster chef Marcus Samuelsson, the island’s approach to haute cuisine has taken a chic turn. Housed in the Hamilton Princess hotel with its landmark pink facade, the restaurant boasts a vibe that’s contemporary and airy with an emphasis on the turquoise sea. All tables have excellent views of Hamilton’s harbor, and the menu is—as might be expected—seafood-heavy, with dishes like Oysters with Black Rum Mignonette and grilled salmon. The local catch of the day and island-grown onions, along with other dishes, are prepared on a wood-fired grill that’s visible from the dining space.

Those looking for some island spirits may be surprised to find that the liquid concoctions at this historic outpost are body products, not liquor. Invented in 1838, the signature blend of bay leaf oils and island-made rum hydrates and nourishes skin. The unisex bars and tonics are infused with various spices, including lime, cinnamon or orange blossom.

You can drive the 71-mile circular road around Tahiti Nui in a day, either by renting a car for a day or by joining a guided tour (your hotel will have info for either). Either way, the loop road takes you along the wild and rocky east coast, where you will see spectacular black sand beaches, many hosting excellent surf breaks. By contrast, the island’s west coast is tamer and features peaceful lagoons for swimming and even a few white sand beaches, like popular Maui Beach. Extend the drive by continuing into Tahiti Iti, the smaller section of the island at the south end, and forming a figure eight loop to return to Papeete.

It’s diminutive, to be sure, but “Little Grape Island” has a big claim to historical fame: Christopher Columbus landed here in 1502, anchoring his ships for repairs. Since then, a lot has happened (and been rumored to have happened) on this now-uninhabited island. It even once served as a quarantine site during a leprosy outbreak. Today, it’s an easy and interesting day trip for beach lounging, surfing and hiking. Take a boat over to the quiet spot and play modern-day explorer, keeping an eye out for colorful bird and fish species.

The isolated, car-free island of Käringön is a 40-minute ferry ride from Orust, and has less than 100 full-time residents who stay year round, even through the long winter. But it’s a different story in the summer. In the 19th century, the middle classes in Sweden became enamored with the benefits of fresh sea air and started flocking to the small islands along the coast. Today about a thousand visitors arrive daily by ferry or private boat to enjoy the island’s relaxed vibe. Come for a lunch of fresh-caught seafood at Petersons Krog or watch children on the pier trying to catch the little crabs crawling through the seaweed down below. In the cold weather, visitors can take a lobster fishing tour or sample fresh oysters at the Käringö oyster bar, which also has a hot tub that seats six.