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From a members-only beach club in the 1960s, The Dunmore has evolved into a 16-room boutique stay whose spirit and decor evoke that era. Local interior designer Amanda Lindroth oversaw a major renovation when the hotel’s current owners bought the property in 2010. Wicker and rattan furniture, patterned prints, and spaces that are as much outdoors as indoors create a look that is somewhere between late British colonial and timeless Bahamian. Although the landmark sits on Harbour Island’s Pink Sands Beach, a pool with an airy pavilion adds to The Dunmore’s reputation as a place of amiable gathering. After a day of sunfilled fun, head to the on-site restaurant, where chef Cindy Hutson, one of the region’s rising culinary stars, prepares modern twists on island delicacies—think grouper curry with lychee and grilled pineapple and banana fritters with rum caramel.

The recently renovated and reopened Philadelphia History Museum showcases an impressive collection of art, objects, and artifacts spanning 330 years of the city’s history. Dating back to 1826, the building itself plays into the journey through the past. The biggest draw for me, however, is the rotating Made in Philadelphia exhibit which looks at the city’s contributions in craftsmanship and manufacturing throughout history (particular nod to the ‘Craft Brewing’ feature which focuses on brewing from the days of William Pen right up through the revival of microbreweries in the 20th century). And if you’re keen on vintage Philly, I highly recommend the much-lauded Facebook page Old Images of Philadelphia. It isn’t associated with the museum but offers a heartwarming virtual walk through the city’s storied past.

Visitors to Philadelphia should not miss out on an iconic local treat—the soft pretzel. Sure, you can find them pretty much everywhere in Philly, but the real deal is baked fresh daily. At the Reading Terminal Market, go to the place where they’ll roll and twist the dough right in front of you—Miller’s Twist—where the soft pretzels are fresh, hot, and buttery (and beyond delicious). Locals line up here daily for fresh soft pretzels and pretzel dogs (hot dogs rolled inside a pretzel bun). There are only fresh pretzels here, still warm from the oven, baked to golden perfection, and brushed with melted butter. The aroma is intoxicating. You’ll want more than one! Save room for a milkshake made with fresh local ice cream.

The newly refurbished Sheraton Kona Keauhou Bay Resort is stylish, with a large pool and water slide. But it was the history and the view from the hotel (located off the famous Ali’i Drive) that won me over. The hotel gives you an excellent vantage point to the bay around which King Kamehameha III was born (stillborn, as legend has it). He grew up to become Hawai’i’s powerful and benevolent ruler, and sought to unite the people. He called The Big Island his home and is beloved by many. The hotel offers several notable cultural markers, including two heiau (Hawaiian temple) replicas.

Located in Leslieville in the East End, Swirl is in a small, converted apartment above a dog store in Leslieville. I love the decor here, from the tables made from doors or antique sewing machine bases to the artwork by local artists FAME. It’s a tiny place but it packs a punch. There’s no kitchen, so they have these amazing appetizers and desserts preserved in small Mason jars. Wine prices are affordable (and they have about three beers available now). On top of all of that, they host theme nights. For instance, you can watch Mad Men whilst sampling accurate cocktails from the era; board game nights; bubbly nights; and cinema Sundays. Suffice it to say, it’s one of my favorites. Warning: it’s tiny in here. Not meant for a big group, but perfect for a date.

Blue Heaven is a favorite in Key West—Jimmy Buffett even mentioned it in one of his famous beach tunes. The whimsical courtyard is filled with brightly colored tables and chairs, twinkly lights, foliage, and stray animals. The bar and restaurant is owned and operated by a husband and wife whose creative backgrounds in art and literature inspired the space. There’s a mini art gallery, a sandwich shop, and roaming roosters on the grounds. Once a boxing ring (with Ernest Hemingway as referee), the spot now pays tribute to the Caribbean, with bright accents and Cajun seasonings on the menu. Menu highlights include the scallops, which are locally celebrated, served with white wine and lemon butter with tomatoes, onions, mushrooms, and lots of garlic. Locals say the Key lime pie is one of the best in town.

Talk about a beach day. This feet-in-the-sand eatery serving burgers, chicken wings, and fries is more than a laid-back fish shack. Sure, there are all the requisite beach-bar amenities—a cool cocktail list, live music, and a line of loungers facing the water. But additional perks include free Wi-Fi, showers, and lockers; what’s more, concession stands are on hand to rent out water-sports gear. The bay itself is breathtaking with limestone rocks creating a barrier protecting it from the open ocean, meaning the shallow turquoise waters are perfect for paddleboarding. Tobacco Bay is also one of the best snorkeling spots in Bermuda.

Dedicated in 1928 after an earlier church was razed and rebuilt, the Immaculate Conception Co-Cathedral is typical of Catholic architecture, with two cross-topped towers, a central rosette window, and a cruciform layout. The church is open for visitors to attend mass on weekdays at 6:30 a.m., Saturdays at 6:30 p.m., and Sundays at 8:30 a.m.

There isn’t much to do in Laborie, but the colorful spot on the southwestern coast offers visitors the experience of an authentic St. Lucian fishing village. The point is to slow down to local speed. Enjoy the views of the white-sand shore lined with pirogues, the traditional fishing canoes. Walk around the village, where plywood homes and ancient churches exist alongside newer structures. Whet your appetite with a trip to the open-air market, where you’ll spot green figs (bananas) and cassava bread for sale. Settle in for a grilled lobster lunch with a side of breadfruit at Mama Tilly’s. Then walk north along the water to Rudy John Beach Park, a shaded stretch of sand ideal for an afternoon nap and sunset.

The friendly vibe at Delly Deck makes island eatery an ideal spot for celebrating special occasions or just grabbing breakfast or lunch with friends and family. Considered by locals to be a landmark (it’s been around for 40 years!), Delly Deck has a solid breakfast menu, with a range of omelet choices and standard but tasty lunch selections such as sandwiches, wraps, salads, and burgers. Cocktails—frozen and not—as well as beer and wine are on offer, though you probably can’t get into too much trouble before the 4 p.m. closing time.

The Plaza Independencia is the most important square in Montevideo, connecting the Ciudad Vieja and the city’s downtown. Several of the city’s most famous landmarks are located here, including the Palacio Salvo and the Teatro Solís. Dominating the heart of the formal square is the Artigas Mausoleum, which houses the remains of José Artigas, the man who declared Uruguay’s independence from Spain at the beginning of the 19th century.

Named after Louis Mountbatten, Britain’s supreme allied commander in Southeast Asia, Mountbatten Road was originally known as Grove Road. In the late 19th and early 20th centuries it became a popular place for the wealthy to build country homes just a few yards from the sea and its refreshing breezes. Today, due to land reclamation, the sea is more than half a mile away. A number of them, nicknamed “millionaires’ bungalows,” were single-story houses with conical roofs that were built on brick posts for protection against heavy rains, snakes, and wildlife—a design modeled after similar dwellings in tropical India which provides the cooling effects of under-floor ventilation.

The Old City neighborhood has sometimes been referred to as the most historic square mile in the US. In addition to being the location of the iconic historic attractions, it is a thriving arts and shopping district with dozens of art galleries and trendsetting boutiques. Highlights include the Book Trader, the Clay Studio, Muse Gallery, and Brave New Worlds (a shop selling comic books and toys). Looking for cutting-edge bar tools and supplies, as well as creative distilled spirits? Art in the Age carries those products and hosts tastings and workshops for home bartenders and distillers. The Center for Art in Wood has a permanent collection of pieces, as well as a gallery with changing exhibitions and a great shop. If you’re spent after all that browsing, revive yourself with a sweet treat from Tartes Bakery at 212 Arch Street.

On Tahiti’s west coast, the area around Punaauia town has some lovely stretches of black and white beaches between PK10 and PK15. This is considered Tahiti’s gold coast of sorts, as it is home to some of the most expensive real estate on the island, and also boasts stunning views across the water to Moorea -- try to stay for at least one sunset. You’ll also find some good shore surf breaks along this strip of sand and for divers the St Etienne Drop-Off just off the Punaauia reef is a wonderful wall dive.

Macao, the world’s largest gambling destination, is a one-hour ferry ride from downtown Hong Kong. A former Portuguese colony, Macao is now a semiautonomous special administrative region of China. Dozens of big brash casinos and their hotels fill Macao’s nine square miles: the Venetian, complete with gondolas and canals; the floral-themed Wynn Palace; the Hollywood-inspired Studio City; and the chic and elegant Parisian Macao with its own replica Eiffel Tower. There are more than a dozen Michelin-starred restaurants and no shortage of glitzy entertainment featuring theater, music, magic, and acrobatics.