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This dockside restaurant has a charming historic patina, as it is part of an actual fishing club headquartered in an 18th-century military Cartagena fortress, San Sebastián del Pastelillo. Sit at outdoor tables with views of the city, the bay, and the club’s private marina and pier (some of your fellow patrons arrive by boat!), and dine on freshly caught seafood. On weekends, live music—jazz, bossa nova, and flamenco—animates the scene.

San Sebastián, for many, is a surf town. Pukas is your one-stop shop for everything from surf lessons, bikinis, gear, and cool souvenirs with a local twist, like their trademark ‘Surfing the Basque Country’ t-shirts.

At La Cuchara de San Telmo, on the corner of the plaza Valle Lersundi in San Sebastian, the specialties were hot pintxos, quickly prepared to order--from the menu or the specials board, or by pointing to what your neighbor was eating. This was one of best scallops I have ever tasted. But then, so was the second one we had when we returned after another hour or so of pintxo bar hopping in the Parte Vieja (Old Town).

Barranco, one of the city’s most beautiful neighborhoods, awash in character, is known for an artsy vibe and gorgeous colonial buildings. Cross the Puente de los Suspiros (Spanish for “Bridge of Sighs”) and follow the Bajada de los Baños to the seaside. Explore the side streets and duck into cute cafés and art venues, including the Museum of Contemporary Art (MAC). The gallery-shop Dédalo, in particular, is ideal for combining coffee, snacking, shopping, and art viewing. Visiting another Barranco landmark, the belle epoque Hotel B, provides a quick trip back to a time of elegant architecture. Splurge for a smart cocktail on the rooftop bar to linger a little longer.

Mission San Diego is the very first Mission built in what is now the state of California and was built in 1769. Many people come to California for what is known as the “Mission Trail”, a tour of all the Missions built in the state by the Spaniards. You can take a tour for $2 and it is still a working Mission, so if you’re Catholic (or not) you can attend Mass.

There are plenty of fancy doughnut shops. You know the type, the ones that count bacon or basil in their ingredient list. But if you’re looking for an old-school bastion of fluorescent lights and pink boxes full of fried dough, this is the spot. A family-run joint that has supplied prework breakfast and postbar bingeing since the 1960s, Bob’s draws a crowd day and night for the fresh doughnuts made from scratch. Bob’s bakes all the nostalgic favorites: glazed, chocolate, sprinkles, sugar, and fresh apple fritters, and crumb-topped doughnuts. You might also notice a giant doughnut in the window. Like a dare, this doughy beast invites you to take Bob’s Big Donut Challenge. Finish the beast within three minutes, and you’ll get your money back plus a Bob’s Donuts T-shirt and bragging rights, not to mention an inevitable stomachache.

Haleakala, a huge and dormant shield volcano, forms more than 75 percent of Maui’s landmass. As such, it pretty much demands you ascend its slopes and peer into its crater—the island’s very soul. Legend claims the demigod Maui snared the sun here, freeing it only after it swore to inch more slowly across the sky.

The 38-mile, two-and-a-half-hour drive up Haleakala climbs from sea level to 10,023 feet through several different ecological zones. One of the most popular ways to experience the volcano remains cycling down from the summit at sunrise. Do it yourself if you’re confident, or join a guided tour (Skyline Eco-Adventures offers one that includes a zip-line ride). Once you’ve mastered the motion—and the 21 switchbacks along the road—effortless downhill freewheeling rewards you with unsurpassed views of the island. If you’d rather savor the vistas from a lofty perch, drive to the top for the sunset or book an overnight at one of the park’s wilderness cabins, accessible only by hiking trail.

Conquistador Pedro de Valdivia founded Santiago here on February 12, 1541. Eventually two Spanish fortresses were erected on the hill, alongside early hermitages and Chile’s first astronomical observatory. You’ll also find one of the capital’s oldest public promenades, originally from the Spanish-colonial period—lined by the statuary, fountains, and gardens of subsequent centuries—twisting uphill through gardens and past trees that have been preserved over the centuries. These days, couples and students favor the park for long afternoons spent beneath the boughs. Don’t miss the monumental entrance, as well as a Spanish escutcheon in stone, the park’s castle, and the 360˚ city views. For those who like traditions, a blast from an 1824 cannon announces the stroke of noon to Santiago residents each day.

Every Thursday night during the months of November to June, San Jose de Cabo’s galleries stay open late for Art Walk. You can join other art lovers on a casual stroll through the Art District’s many galleries, enjoying work in various media from both local and expat artists. Several local restaurants participate in the Art Walk, too, offering specials or discounts as part of the weekly event.

Oaxacan artist Francisco Toledo spearheaded the project of converting an abandoned textile mill into an arts center, which was inaugurated in 2006. The Centro de las Artes San Agustin (CASA) hosts exhibits of a variety of media, as well as courses and workshops. It is an ecological arts center and encourages artistic creation using environmentally friendly processes, and community involvement. CASA is located in San Agustin Etla, about a twenty minute drive from Oaxaca city. It is open daily from 9 am to 6 pm, and if you go on Sundays, there is an organic market on the grounds (Mercado Los Eucaliptos).

For the time it takes most Angelenos to commute to work, you can be ferried into the alternate reality of Catalina Island, a romantic escape far from the daily traffic jams and urban sprawl. The evergreen-shrubbed hills spotted with an artists palette of summer homes and surrounded by bright hues of blue waters, coves and marinas feels more like the islands off the coast of Spain than the United States. It is rejuvenating to arrive at a place so close to the city yet feel so completely removed.

You’ll likely do your sunbathing and swimming on the white-sand beaches of the Grenadines, but St. Vincent’s black-sand beaches are also quite stunning. In Biabou, for example, along the windward coast south of Georgetown, you can stare for hours at frothy ocean waves crashing onto the volcanic black sand. With luck, you’ll also catch a rainbow.

Easter Island is a strange, remote, and magical place. After a full day of wandering around this tiny island, we were fortunate enough to witness an absolutely breathtaking sunset over the Pacific. The “beach” here is made up of pitch black volcanic stone. I found it to be utterly fascinating.

I think the most appealing aspect of Old San Juan is the architecture and design of the city. Residential apartment buildings have been converted to designer boutiques or little B&Bs, and interior courtyards invite hungry guests to relax and unwind in the shade.... I’ve been to this area multiple times and still I manage to find a street I’ve never wandered down. Some are more popular than others, in particular Calle San Sebastian, which hosts eateries, bars, and shops, and Calle San Francisco. At the corner of this street is my particular favorite, Franky’s antiques. It’s in a four-story building, loaded with vintage goodies. There’s so much to see, one trip is not enough. If you want to shop, consider wandering all morning and into the early afternoon. You’ll be delighted by all the unique shops. Then, take a break at my favorite restaurant, Triana, for Spanish-style tapas and their famous sangria. It’s a must-stop place any time I’m in the old city. You don’t need a car to get around. Just park at one of the garages and explore by foot. There’s lots to see and do in Old San Juan.

While many cities have rivers, few take advantage of their waterways quite like San Antonio does. One of the city’s most popular tourist attractions, the River Walk runs along the San Antonio River and features both quiet stretches for jogging and livelier areas lined with colorful bars, restaurants, and shops. For an immersive experience, take a boat tour and learn more about San Antonio’s history and architecture.