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Kids visiting the Westin will love the resort’s kiddie pool, featuring an enormous waterslide that will make adults envious. There’s also a large indoor-outdoor play area (packed with toys!), mini putting green, and sandbox.

Borrow a bike and get down by the Charles River to explore this popular linear park, which runs along the river through the Back Bay and the Beacon Hill neighborhood (albeit separated from both by the Storrow Drive expressway). A paved, 18-mile multiuse path popular with cyclists, runners, and in-line skaters helps connect the Esplanade to the parklands of Boston’s Emerald Necklace and provides easy access to landmarks like the Hatch Memorial Shell (the summer stage for the Boston Pops and other performers) and Harvard Bridge (aka the Smoot Bridge). The landmark Community Boating boathouse has kayaks, stand-up paddleboards, and sailboats for rent when you want to get out on the river.

This five-star beachfront hotel toes the line between being a hub of activity and a luxurious, only-in-Southern-California hideaway. For restoration, head to the sprawling spa for a customized wellness-oriented treatment or a meditation class. Mind cleared, make your way to the on-site outfitter Compass Sports—where staff will coordinate local mountain biking, paddleboarding, hiking, and surfing expeditions—or to the palm tree–lined, mosaic-tiled pool. Big ocean views and a light, airy design define the 250 rooms; for guests seeking extra solitude and space, there are bungalow suites, which are essentially private beach houses. At the hotel’s three eateries, it’s all seasonal all the time, from the fresh morning juices to evening cocktails. That ethos peaks at the fine-dining restaurant Studio, where executive chef Craig Strong creates elegantly plated French-meets-California dishes using locally sourced fish and meat, along with vegetables picked from the hotel’s 1,000-square-foot garden. Pro tip: In a setting this transporting, you almost want to break into song. Good news—the hotel will rent out mini guitars to guests for the duration of their stay.

The Golden Gate Bridge is probably the most photographed site in California, but this vantage point never gets old. Explore the hollowed out fort, learn some history, and marvel at the view from the top floor.

A quintessential Alpine winter break wouldn’t be complete without scooping dripping molten cheese from a fondue pot after a day on the slopes. Few places offer this traditionally Savoyard experience quite like the warmly elegant La Calèche Restaurant. It’s not just the variety of fondues, raclettes, and tartiflettes which sets this place apart: The Savoyard dishes merge perfectly with the array of black-and-white photos of Mont Blanc hanging on the walls and the wooden sledges and skis hanging from the ceiling. The cozy terrace is ideal for watching skiers heading back home, while on a Tuesday evening a lively costumed folklore group induces singing, dancing, and mountain merriment.

A city of red-tiled rooftops, pine- and cypress-shaded hills, and sparkling turquoise waters, the Old Town of Dubrovnik stuns with both its architecture and scenery. Its surrounding stone walls, built between the 11th and 13th centuries to protect the city from war and epidemics, stretch for a full 1.3 miles, comprising an immense system of forts, bastions, and walkways that offer breathtaking views. Hike along them, then be sure to check out the Lovrijenac Fortress, built atop a 100-foot rock looking out toward Venice (Dubrovnik’s historic rival). The Old Town’s main street of Stradun, known locally as Placa, is also worth exploring. It’s especially nice in the late afternoon, when the sun shines off the historic buildings and swallows soar in the blue sky above.

Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.

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.

I’m not one to skip breakfast, especially in Italy, where thoughts of cappuccino, pastries, and local ham tend to rouse me early from slumber. But on my first morning at the Hotel Sant’Angelo, in the old quarter of Matera, I was having a hard time dragging myself from the creature comforts of my cave. Staying in a cave, it turns out, can be surprisingly pleasant. There was just one small window high overhead, but the room and adjoining bath were in no way dank—a testament to the natural ventilation that keeps the caves cool and comfortable. The wavy contours of the white tufa-rock walls conjured a feeling of being enveloped in some primordial womb. Yet there were modern amenities: luxurious linens, Internet service, a telephone. Fred Flintstone never had it this good. I might have snoozed until noon, were it not for an impatient mate eager to see the sights. We had arrived in the village the previous night after a long drive across the treeless plains of the Basilicata region, located at the instep of Italy’s boot. Matera is an enchanted world of Stone Age splendor. Known as the sassi (Italian for stones), the bisque-colored hilltop cave homes comprise one of the oldest continuously inhabited places on earth, according to UNESCO. The caves have provided shelter for more than 7,000 years. A millennium ago, shepherds inhabited them and carved churches into the rock; during the Renaissance, the area prospered and elaborate buildings were carved out, the excess tufa sculpted into ornate facades. By the early 1900s, the sassi had fallen into neglect. Families and their animals crowded into the caves for warmth, and disease was rampant. When writer Carlo Levi brought this tragic state of affairs to light with his 1945 book Christ Stopped At Eboli, the Italian authorities moved residents en masse to modern housing—leaving the sassi abandoned, save for the occasional crew brought by film makers (Pier Paolo Pasolini and Mel Gibson among them) in search of a biblical-looking backdrop. It was only in the 1990s that the Italian government encouraged people to move back. Residents revamped the cave dwellings as homes, restaurants, and inns. When the Sant’Angelo opened in 2004, it was the area’s first luxury hotel. The 19 cave rooms are sparsely but tastefully appointed with rustic wooden furniture. Some carved decorations—crosses, hearts, an owl—date back hundreds of years. Fossilized shells embedded in the walls reveal that the region once lay underwater. Eventually, my fiancé and I did emerge from our cave to wander the town’s ancient alleys. A local guide named Dora Cappiello took us into some of the 150 chiese rupestri (rock churches), where she pointed out wine troughs and frescoes of San Nicola, the patron saint of local shepherds. We also visited a cave dwelling that had been restored to resemble its state when the caves were equal parts manger and living space.
Simple, delicious meals punctuated our explorations. The curvy walls of Baccanti, a cave restaurant, created a private nook where we feasted on silky pappardelle pasta with a cinghiale (wild boar) ragu, accompanied by a dry, fruity red aglianico from the nearby Vulture wine region. Tired and sated after a full day, we headed back to our cave—on moonless nights, a flashlight or trail of bread crumbs is advised for the stumble back to the hotel—where the promise of a deep, sound night’s sleep awaited. —Amy Cortese Hotel Sant’Angelo, 39/0835-314010, from $211 for a double. This appeared in the March/April 2010 issue.

Shipwreck is a classic Caribbean beach bar with umbrellas (in both the sand and the drinks), snorkeling off the shore, and live music on Sundays from “4ish to 6ish.” Don’t miss the fish tacos, claimed to be the best you’ll ever taste. And bring your phone—the photo to get is one of the local monkeys that frequent the beach.

Standing its ground between a cypress grove and the Pacific Ocean, the Point Pinos Lighthouse is the oldest lighthouse in continuous operation on the U.S. West Coast—and one of seven lighthouses for which Congress appropriated funding shortly after California statehood was ratified. But this lighthouse wasn’t just an aid to navigation; it was also a social hub in early Pacific Grove. Robert Louis Stevenson wrote about lighthouse keeper Allen Luce and his piano playing, while a fondness for entertaining inspired locals to call keeper Emily Fish the Socialite Keeper. The lighthouse beacon, a third-order Fresnel lens, has flashed nightly since 1855 and is still used in the tower today—the light is visible up to 17 nautical miles out to sea. Docents are on duty to answer questions as you tour the lighthouse, from the 1890s-style parlor to the 1920s-style kitchen, and up to the Emily Fish bedroom and lookout. Right behind the lighthouse is the El Carmelo Cemetery, one of the most peaceful seaside cemeteries, with deer wandering through to nibble on the grass.

Like nearly every Latin American city, Santiago has at its heart a civic square open to the public and brimming with life (and these squares are often named Plaza de Armas). Santiago’s Plaza de Armas is distinguished by two fine buildings, the Central Post Office and the Metropolitan Cathedral. Both buildings were constructed in the 18th century, although the cathedral was much altered in later years. The square is full of lively activity—an excellent spot for people-watching and getting to know this city’s energy.

Before Columbus arrived in the West Indies, indigenous tribes had lived on Puerto Rico for at least 2,000 years. The Igneri were the oldest recorded inhabitants, followed by the Taino, and artifacts from both peoples have been found at the Tibes Indigenous Ceremonial Center, a settlement just outside of Ponce that flourished from roughly 400 C.E. to 1000 C.E. Many of the artifacts are on display at the on-site museum, and a replica Taino village shows how native Puerto Ricans lived in the pre-colonial era.

This playful picnic and wine shop is quintessentially Ojai. Set in an old Spanish house, Tipple & Ramble sells indoor/outdoor decor, vintage and new barware, retro games, coolers, and small-batch specialty food items. Stock up on artisanal s’mores kits for your next campout; cocktail mixers and trays for entertaining; or cheese knives and handmade cutting boards for a stylish picnic. Then step onto the patio, which feels like entering a neighbor’s bohemian backyard, a lush landscape of palms, cacti, and hammocks. On Thursdays through Sundays from noon to 7 p.m., the patio becomes a wine bar. Try a cheese and charcuterie board or hummus and seasonal vegetables, paired with wine, beer, or Mexican Coke from the bar, which is built into a vintage trailer. Pro tip: The patio faces east, the essential direction to enjoy Ojai’s Pink Moment—the famous sunset that turns everything a glowing pink. Plan to arrive early enough to get a glass of rosé and snag the table in the front of the yard for the best end-of-day view.

What began as a recreation area for immigrants from Brazil’s northeast is now a destination for visitors looking to get off the beaten tourist path. The densely populated São Cristóvão quarter is home to this enormous complex, open seven days a week, to which visitors may arrive at a reasonable hour and not get out before dawn. Afternoons are for shopping and noshing; but after dark, the volume goes up, and the marketplace becomes a scene for partying, pop-up karaokes, and live-music performances that are 100-proof Brazil. Authentic northeastern music known as forró plays until sunup.