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Looking for a great afternoon or evening hike, high above the clouds of the East Bay? Need a few good labyrinths and a volcano to make it desirable? It so happens, I’ve found your place. Located on the border of Oakland and Contra Costa, the parking for Sibley is on Skyline Boulevard. This is a Regional Preserve and is managed by the East Bay Regional Park District. All the perks of hikes in this part of the Bay are here and include a great network of trails, soaring views and many a grassy vista. It also claims an extinct volcano and at least four or five labyrinths for potential meditation. You have two major continental plates to thank for the geological grandeur and a few thoughtful locals for the peace of mind, found within.

The moment the snow melts, young Torontonians begin their annual spring migration to Trinity Bellwoods Park. The hippest park in town, Bellwoods stretches from the shopper’s paradise of Queen West up to central Dundas Street. On a summer’s day, sun-and-fun seekers spread out on beach blankets to watch the action: at the dog run, on the tennis courts, in the kiddie pool, and even closer, on the adjacent blankets. After dark, head to nearby Bellwoods Brewery for a pint.

Among the three Cayman Islands, Brac is the most topographically endowed, thanks to its distinguishing feature: the Bluff, a limestone cliff rising along the length of the island and topping out at about 140 feet at the eastern end. Between that and the island’s densely forested interior, the local hiking options have a lot to offer—one of the best cases in point being the Lighthouse Footpath, a trail that runs two and a half miles (one way) along the bluff’s edge and that serves up endless sea views and likely encounters with the absurdly adorable brown boobies and soaring frigate birds. Try to go in the morning or late afternoon, and of course, take along plenty of water: You’re looking at a two-hour outing to the most beautiful of boonies.

In the southwest of Providenciales, this national park encompasses the tranquil Chalk Sound lagoon, a large expanse of shallow water connected to the ocean by a small channel. Check out the fringe of jagged limestone, called ironshore, along the shorelines of the lagoon and its small islets. You can rent a car and explore scenic Chalk Sound Drive, or you can stop at Las Brisas Restaurant to rent kayaks for a paddling adventure. See if you can spot stingrays and small sharks finning through the water, or the local rock iguanas foraging on the islands.

As of May 2018, El Conquistador Resort and Las Casitas Village are closed indefinitely, due to damage sustained during Hurricane Maria.

Situated atop a 300-foot bluff on the eastern tip of Puerto Rico, El Conquistador Resort, a Waldorf Astoria Resort, spreads across 500 acres overlooking the converging waters of the Caribbean Sea and the Atlantic Ocean. A stay at El Conquistador is a transformative experience. Guests can relax at the Eucalyptus steam room, enjoy exotic cocktails while gazing at the El Yunque Rainforest, or even kayak around a private island. Guestrooms and suites are divided into five villages, and feature ocean views, 23 restaurants, an 18-hole golf course, a state-of-the-art aquatic playground/water park for families, and the resort’s private island, Palmino Island, featuring water sports and white sand beaches.

Hogfish Bar and Grill, under a thatched palapa roof with open sides, is tucked in among the boats and gulls of Safe Harbour Marina in Stock Island. In short, a meal or a drink there makes you feel like an insider, a salty local far from the crowds downtown. That in-crowd feeling is burnished on weekends, when local bands play sets, or during one of the events held by Hogfish during the season, like shrimp boils. The simple food is served generously on plates crowded with side dishes. The hogfish sandwich, served fried on Cuban bread, is the stuff of late-night-post-beer legend.

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.

Checking out the famously preserved mummies at the world’s oldest public museum is on many London wish lists, but there’s much more to the British Museum than ancient Egypt. Other must-sees include the Elgin Marbles and the African masks, both part of an enormous collection that spans ancient Iran to modern Sweden. The Great Court, which was cleverly revamped with a geometric glass roof by Foster + Partners in 2000, is a spacious gathering area with a shop and a café—and a sight worth seeing in itself.

Store Bay, just outside Scarborough, is one of Tobago’s most popular beaches. Reserve some time after your swim for a visit to the dozens of bright and cheery craft shops and food stalls that make up the Store Bay Beach Facility. Need souvenirs? Browse for island crafts like batik, sandals, jewelry and items carved from wood and coconut shells.

This 1763 plantation house has an interesting tale to tell. It never employed slave labor, and its owners—descendants of Carib Indians—are commemorated with statues and figures spread throughout the rooms and gardens. Visitors can take tours of the house, gardens, and old overseer’s house, then enjoy beautiful views of the neighboring island of Nevis.

Yo, ho, ho and oh, my! Up on Government Hill, this watchtower, built circa 1678, is known as Blackbeard’s Castle and is literally the stuff of legends. Although it’s open for debate whether the notorious pirate ever used the five-story tower as a lookout, one thing is for certain: Its views are tops. Nearby the flower-lined 99 Steps (technically there are 103), built in the 18th century of ship-ballast brick, lead from historic Kongens Quarter to some more terrific views of the island.

Jambe de Bois is an unpretentious food escape set idyllically in Pigeon Island National Park. The café—made of stone, driftwood, and thatch—serves up a beach view, an island atmosphere, and a simple menu that will keep you happy for hours. Sit on the deck at one of the picnic tables, and snack on sandwiches, salads, or local dishes like rotis, curries, or fish fillet with rice and peas at lunch and dinner. Come for happy hour or join the locals for live jazz on weekend evenings. The local art on display inside is for sale.

On Tahiti’s rocky east coast, the volcanic Lava Tubes of Hitiaa are underground channels and eroded sections of rock in caves that have been penetrated by water. Although you can visit solo, it is really best to visit with a guided 4WD tour. Check with Marama Tours, which also does a range of other island tours from encounters with dolphins to 4WD trips across the Papenoo valley that is rich in waterfalls and archeological sites.

I love finding Love Locks all over the world. Sydney did not disappoint with a collection on the Sydney Harbour Bridge, with a perfect view of the Opera House.

This honky-tonk-inspired bar has a hometown feel and a country vibe, and has great local beers on tap—like Grand Cayman’s classic premium lagers, the CayBrew and Caylight. Don’t miss out on the Thursday night Rock & Roll Bingo: It can get rowdy and is a lot of fun. Lone Star Bar and Grill is well known for its BBQ, including Texas-style ribs as well as barbecue chicken and burgers. When you get the munchies after a few beers it’s a nice break from the gamut of seafood offered at other establishments.