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Montevideo’s Ciudad Vieja, or Old Town, is located on a peninsula separating the Río de la Plata from the harbor. It has the orderly grid typical of many Spanish cities in the New World. Until 1829, the Ciudad Vieja was walled though today only one gate (the Puerta de la Ciudadela) remains of those defenses. This section of Montevideo is home to many of the city’s most famous historic buildings, including the cathedral and the Cabildo, which today houses the city’s archives.

The edges of the iceberg (technically, bergy bits) are a great place for animal sightings. Harbor seals ride the floes, basking in the sun; orca whales prowl just around the ice barrier, waiting for an unwary seal to come out to where the whales’ sonar can reach. Humpbacks feed off krill upwellings, and bald eagles are as common as sparrows. Those who are very lucky (and who have good spotting scopes) can see mountain goats on occasion. They’re a wonder in the wild: How does a goat get up 3,200 meters of rock?

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.

Whether you want to explore the stretch of sand dunes 40 minutes outside of Dubai or visit the largest expanse of uninhabited desert in the world, known as the Empty Quarter, a desert safari is the way to do it. There are any number of tour companies that will set you up for the adventure, which usually includes exhilarating (sometimes terrifying) dune-bashing rides, in which you’ll slide up and down the dunes in a 4x4; an Emirati-style supper under the stars; and, of course, a camel ride. Platinum Heritage can tailor its outings to the needs of your particular group.

Mile-long Newbury Street, lined with handsome 19th-century brownstone homes, is synonymous with shopping in Boston; it’s also the place to go to get your hair done up nice. Between Arlington Street and Massachusetts Avenue you’ll find an eclectic mix of boutique and designer shops, hair salons, art galleries, and restaurants that generally skews upscale (Tiffany’s, Chanel, Dolce & Gabbana) but also includes the original location of the Newbury Comics record store and a T.J. Maxx. Eminently strollable and dotted with sidewalk cafés, Newbury Street is the hip heart of the Back Bay neighborhood, perfectly distilled at eye-candy drinks-and-dining hot spots like Sonsie and Stephanie’s on Newbury.

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.

Fish from tins, fish whose fins were in the sea just this morning—they’re all stars at Saltie Girl, a compact seafood bar and restaurant in the Back Bay from Kathy Sidell of MET restaurant fame. Whether you love your seafood raw, smoked, fried, or—yes—out of a can, settle into one of the 11 stools in front of the active kitchen to watch as your dinner is prepared or, well, opened. Of course, you’re not paying top dollar for Chicken of the Sea here: The tinned seafood comes from small artisan producers, sustainably sourced, packed fresh, and shipped from around the world. Caviar, squid, anchovies, cod liver, and cockles are among the savories served cold with dipping sauces and crusty bread.

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.

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.

The Thermal Water Pool of Terra Nostra Park is without doubt a highlight of the Azores. Built in 1780, by Thomas Hickling, the American consul who had the original idea for Terra Nostra Park, the Thermal Water Pool began to form part of the assembly dominated by Yankee Hall, a holiday house owned by Hickling. The pool was significantly smaller at that time, but already consisted of an “island” in the middle, with a bridge linking it to the land. The Thermal Water Pool was enlarged in 1935, acquiring its present form, with the refurbishment of the Park, operated by Vasco Bensaude. It was also enhanced by quarry stone masonry, remaining unchanged to date, undergoing only a few minor repairs.

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.