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Located in the heart of Bridgehampton, Topping Rose House occupies a grand old Greek Revival mansion, built back in 1842 for a local judge. The luxurious property features 22 guestrooms, including a number of cottages, with elegant décor like four-poster beds and glass doors that open onto verdant grounds. Also on site is a Jean-Georges Vongerichten restaurant, complete with a seasonal menu that incorporates ingredients from the property’s one-acre farm. Unusual for a small Hamptons hotel, Topping Rose offers a wide selection of amenities, including a lovely outdoor pool, a fitness center, yoga classes, and a spa with a range of massage and beauty treatments.

Rugged Monhegan, aka the Artists’ Island, lies about a dozen miles out to sea, and is reachable only by passenger ferries. About 60 hardy souls live here year-round, most making a living from the sea. If you get a sense of déjà vu when visiting Monhegan, it’s likely because so many of the island’s icons and vistas have been painted by American masters, including Robert Henri, Rockwell Kent, Jamie Wyeth, George Bellows, Edward Hopper, James Fitzgerald, Andrew Wyeth, Alice Kent Stoddard, Reuben Tam, and William Kienbusch. Artists and art lovers come in summer; bird-watchers flock here in spring and fall. Hiking trails access remote rocky beaches and craggy headlands. Go for the experience, the art, and the hiking, and don’t miss the museum at the lighthouse.

A UNESCO World Heritage site, this 1,700-year-old palace sits on the Adriatic seafront, serving as the focal point of Split. It was built by the Roman emperor Diocletian as a seaside retirement home and has served as a refuge for many a conqueror over the centuries. Today, some 2,000 locals reside within the compound’s thick walls, making it a lively urban quarter. Getting lost in the labyrinth of surrounding streets is the best way to explore downtown Split—as you meander around, you’ll stumble across lively cafés and shops tucked into millennia-old buildings. Be sure to check out the Peristil, an imperial square framed by two colonnades, where Diocletian used to address the public. Towering above the square is Split’s major landmark—a 187-foot-tall belfry that you can climb for panoramic views of town.

Cerro Ancón, or Ancón Hill, is a patriotic symbol for all Panamanians. While the Stars and Stripes waved atop the hill throughout the period of United States control of the canal, now the proud promontory displays Panama’s colors. There’s just one footpath that leads to the top. In addition to its historical significance, it’s worth scaling the peak to visit the surrounding jungle and catch a glimpse of the area’s wildlife, all of which makes the park an oasis amid big-city bustle. Cerro Ancón’s second-generation, restored forest is home to more than 260 plant and 70 animal species. Once you hit the summit, every vantage point offers views of the Casco Viejo, the modern metropolis, the harbor, and densely populated downtown districts.

One of the best places to feel the local side of Reykjavik life, the Kolaportid Flea Market is set in a spacious industrial warehouse close to the city’s old harbor. Open at weekends only, you can find anything from wool jumpers and vintage fashion garments to fermented fish and licorice, plus plenty of second-hand books and decorative knickknacks. Best to go early to avoid the crowds (it opens at 11 a.m.)—and best to have cash on you since many of the market’s vendors don’t accept credit cards.

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.

If you’re looking for a party atmosphere and excellent people-watching, this restaurant/bar positioned near Hamilton’s harbor is your spot. It serves breakfast, lunch, dinner and late-night snacks. DJs spin and live music is performed throughout the week.

Who wouldn’t trade an ugly elevated highway for a ribbon of new parkland? Boston’s famous Big Dig dismantled the eyesore John F. Kennedy Expressway that long separated downtown from its waterfront and turned most of its former route into a linear park named in honor of JFK’s mother. The Rose Fitzgerald Kennedy Greenway snakes for a mile and a half from Chinatown to the North End, mostly parallel to Boston Harbor. It’s a pleasant alternative to walking the city’s busy streets to get around, and you can use the park’s free Wi-Fi to plan your visit. Along the way you’ll find seven decorative and interactive fountains; a carousel where lobsters, codfish, harbor seals, and other local animals take the place of horses; and a variety of food trucks for when you need to recharge with a taco, a grilled-cheese sandwich, or a cupcake. The Greenway’s visitor center for the Boston Harbor Islands National Recreation Area has information and ferry tickets.

At Thunderbird Lodge, you can marvel at the eccentricities of the fabulously wealthy real estate magnate George Whittell, Jr., who built this 16,500-square-foot mansion on Tahoe’s east shore to house himself, his pet lion, and a small elephant. Walk through the 20-plus rooms and the 600-foot-long underground tunnel that connects the main house to the cavernous boathouse, which Whittell constructed for his 55-foot-long speedboat, the Thunderbird, a gorgeous 1939 woody that’s still available for charter cruises. Also on the 140-acre lakefront property are a lighthouse and several guest cottages. Guided tours are offered five days a week from mid-May to mid-October; arrive via boat or shuttle bus from Incline Village, or kayak over from Sand Harbor State Park.

Located on the north coast of Isla Robinson Crusoe, Cumberland Bay sits in the shadow of the volcanic peaks that form the spine of the island. Along the bay is the island’s only settlement, San Juan Bautista, a quiet town of fishermen living in modest homes. Below the sea here is an artifact of a moment when the island played a brief part on the global stage. The German SMS Dresden was launched in 1908 and took part in the Battle of the Falkland Islands in December 1914, during World War I. The ship then sought a safe harbor on Isla Robinson Crusoe, as Chile was neutral in the war. British ships, ignoring Chile’s neutrality, attacked the Dresden and its captain intentionally sunk the ship. It remains to this day resting on the bottom of Cumberland Bay.

A mixed-use space for art, education, and history—inside a restored early-20th-century palace—the Museu de Arte do Rio (MAR) is a landmark in the city’s harbor zone. Walk from the top floor down, fifth to first, following an exhibition itinerary that touches on different elements that have left their mark on Rio’s rich history. At the end of the visit, go back upstairs for some refreshment at the excellent terrace restaurant that offers boffo views of Guanabara Bay. On the plaza out front, the Museu do Amanhã (Museum of Tomorrow), a science museum housed in a stunning building designed by architect Santiago Calatrava, can provide a visit that nicely pairs with your MAR expedition.

After falling in love with Salvador Dali at his museum in Figueres, we caught one of three buses out to the cliffside town of Cadaques where you can get to know Dali a bit more intimately by touring his house. Full of odds and ends, including mini cages where he kept crickets and a polar bear draped in jewels, his house also includes spectacular views (including this one) of the serene Port Lligat. Tips: You must book tickets in advance to tour his house, and double-check the bus schedules because there are only three buses per day that go from Figueres - Cadaques and back.

Harbour Island is an out island of the out island Eleuthera in the Bahamas. Home to a scant 1,500 people and more golf carts than cars, Harbour Island is the perfect place to get away from it all. It’s also home to the rich and famous who visit for the same reason the rest of us do, quiet relaxation. As soon as I landed on the island I could feel my stress melt away. It’s hard to get too worried on an island with roosters in the street and golf carts whizzing past. Harbour Island is one of those places that quickly occupies a place in your heart and I know I can’t wait for a return visit.

Every book will tell you to have high tea at the Empress in Victoria, and you should. They welcomed our three-generation group, including 2 kids under 6, and had hot chocolate for those who didn’t want tea. They also had a full gluten-free option, which was a very welcome surprise. I recommend the Empress blend tea with milk and sugar, and the peppermint also got the stamp of approval from our group. The tri-level tray of treats is the fun part: chicken curry finger sandwiches and cake wrapped in marzipan were the faves. It’s actually fun and not stuffy at all, which was my fear.

This scenic and flat 20-mile round-trip bicycle route follows the waterfront promenade that wraps around Tolo Harbour, which makes a ride an excellent way to combine an easy bit of exercise with sightseeing. Enjoy views of the eight peaks of the Pat Sin Leng mountain range as you pedal and soak up the ultramodern architecture of the Hong Kong Science Park. At the Tai Po Waterfront Park, climb the 105-foot lookout tower to snap photos of panoramic harbor and park views before heading back the same way you came. The full round-trip ride takes two to three hours, depending on how often you stop for photos. Join a guided tour, or go solo and rent bikes by the Shing Mun River at Sha Tin Park near the Sha Tin MTR station.