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With more than 400 shipwrecks and its fair share of coral reefs, St. Kitts is a favorite of the scuba set. To try your hand at the hobby, consider staying at Bird Rock Beach Hotel, which houses one of the island’s most popular dive operators. Here, guests can charter a boat to nearby Devil’s Cave and swim among barracuda, lobsters, and nurse sharks, then retire to one of 46 tropical-hued rooms overlooking the sea. Less adventurous travelers can visit the on-site dolphin park, sunbathe on the private beach, or simply sip rum punches from the pool’s swim-up bar. Hotel staff is also happy to arrange off-site activities like catamaran cruises, rainforest treks, and volcano crater tours.

Set amid the mangrove swamps, coastal lagoons, and stretches of coral reef in Portobelo National Park, this Design Hotels property features just five colorful villas. The “houses” range from a small, one-bedroom retreat nestled near a waterfall, to an over 8,000-square-foot residence spread over two floors. The whole property is awash in a kaleidoscope of vibrant hues, from the bright interiors with their boldly patterned tiles, decorative fabrics, and local artwork, to the multi-colored lounge chairs surrounding the infinity pool, which seems to merge seamlessly with the turquoise Portobelo Bay. Those seeking adventure can take a deep-sea dive to explore the wreck of a C-45 airplane, while guests looking to relax can book an outdoor massage on the hotel’s century-old barge.

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.

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.

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.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

Every December 7 at Pearl Harbor, there is a memorial to those who died in the awful attacks that day in 1941. Survivors gather here, though fewer every year remain alive. Oil still rises from where the USS Arizona lies in the harbor. The horrific events of December 7 are still a raw part of the history here. Several months ago, the civil defense sirens went off all over Oahu. It was a glitch in the system, but I remember an elderly woman in downtown Honolulu who said she looked at the sky because she remembers when there really was an air raid, and the sirens bring her back to that time of eminent danger when what seemed impossible unfolded in front of her young eyes. For history buffs, students, and all sorts of tourists, this is a “must visit” National Park on Oahu. Tickets to take the boat to the memorial are cheap (but do require an advanced booking of a couple days), and there are several other activities and museums at Pearl Harbor to explore including a walk through the USS Bowfin.

At the Big White Ski Resort there is more to do than ski and snowboard which is especially useful to know when you’re not a skiing Canadian like myself. Instead of hitting the slopes there are snowshoe excursions, ice wall climbing, sledding with inflatable tubes, ice skating, sleigh rides, dog sledding, and, even more importantly, delicious restaurants and bars full of beer and locally produced wine.

One of my favorite discoveries in Chicago is the Empire Ballroom inside The Palmer House. It’s just up the stairs from the hotel’s magnificent lobby and has a rich history most anyone working at the hotel will be willing to tell you more about. This room with its shiny wood floor and opulent chandeliers is where Frank Sinatra used to perform. While the ballroom itself is beautiful, it’s most interesting feature is what’s hidden behind the mirrored wall in its corner. Push on the last panel and you’ll stumble into a dressing room where famous acts - including Sinatra - used to get ready to go on stage. Several autographed pictures are still hanging on the walls.

This beautiful one-mile stretch was donated to the people of the Virgin Islands by Arthur Fairchild, a benefactor of the islands who’d made his fortune on Wall Street before retiring here. The usually calm waters of the heart-shaped bay make the beach the most popular on St. Thomas. Rent beach chairs and floats, and pick up lunch from stands selling burgers, pizza, and other snacks. Lifeguards are on duty every day.

Descended from horses brought over in the 16th century by Spanish conquistadors, hundreds of wild horses rule the little island of Vieques. The horses, an attraction in their own right, dot the landscape wherever you go. With every encounter, I couldn’t help but slow down and admire their beauty. They are naturally intelligent and curious, so don’t be surprised if they approach you or your vehicle looking for little treats. For a guaranteed encounter, look no further than Sun Bay—where I snapped this picture. Here, they graze, take frequent sand baths, and (if you’re lucky) cool their hooves in the blue waters of the Caribbean.