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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.

While the climb is quite literally breathtaking (900 steps), the Church of San Rocco, perched on the very edge of the Ligurian Sea, is a gorgeous spot to spend the day. Taking the train to Camogli, you can then spend the morning hiking up to the church and enjoying the beautiful altar piece and frescoes. Coming back down into town, make sure you stop by one of the many seaside restaurants for a celebratory lunch, and grab a gelato from one of the boardwalk stands on your way back to the train station!

When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.

If you’re in San Sebastián to eat, chances are you’ll be wanting to eat Pimientos de Gernika and Guisantes Lágrimas long after your trip is over. Semillas Elosegui is a classic stop in the Old Part of San Sebastián, and they have seeds for all of your Basque cooking needs. Perfect souvenirs for the foodies on your list.

Santa María del Coro is San Sebastián‘s token beautiful European church. It has the quiet, sunlit beauty that one comes to expect in European churches. It also is the site of several of the city’s unique celebrations, organ concerts, and the iconic San Sebastián, pierced with the famed arrows.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

San Antonio’s west side is one of the city’s cultural hubs. Latin and Mexican-American influences are vibrantly displayed through public art and murals. The area around Guadalupe Street is an especially rich place to explore. You’ll find art around every corner, cultural centers, theaters, coffee shops, and bakeries. One of the best resources I came across was the San Antonio Neighborhood Tours sponsored by the City of San Antonio Office of Cultural Affairs. You can download free PDFs of the guides here: http://www.saculturaltours.com/. We did the West Side Murals Y Mas Tour. It was an awesome experience that included more than 50 unique sites.

Each Saturday from October to July (and once a month in August and September), the marina of Cabo San Lucas becomes a stage for local artists, musicians, and performers to peddle their wares and showcase their creative skills in the Circuito Cultural (Cultural Circuit), an event started by local entrepreneurs. Artists display their work from noon to 10 pm and live music and dance keep crowd entertained from 6 pm to 11 pm. The performances aren’t just Mexican in inspiration or origin; recent highlights even included Scottish country dancing.

The church of the mission of San Jose del Cabo is simple, both inside and out, but one of its charms is a special area where locals tie ribbons with petitions for divine intervention or expressions of thanks written on them. If you’d like to join in on the tradition and express your thanks, choose a white ribbon and write about what you’re grateful for on it. Then, tie it to the rack near St. Charbel Mahklouf, the somewhat obscure Lebanese saint who is believed to work miracles.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Complete with an in-shop florist and white, honeycomb-tiled wall, this light-filled coffee shop is one of San Diego’s most Instagramworthy spaces. Luckily, it offers more than just good looks—the coffee comes from San Francisco’s Sightglass and the menu includes lavender-honey toast, chia pudding, and an assortment of croissants from Wayfarer Bread & Pastry. Owner Jen Byard is also the cofounder of San Diego’s popular Maker’s Arcade, a holiday market that takes place every December, so she has an eye for artisan items. Communal’s retail section is always stocked with tasteful finds like ceramic mugs and Mexican blankets.

In the mid-1800s, the Pioneer Mills family helped found San Antonio’s active flour milling industry. It’s fitting that their private residence, the Guenther House, is now home to a local history museum and a delicious restaurant that serves some of the best pancakes in San Antonio. The pioneer biscuits and waffles are also a favorite best enjoyed riverside. Come for the food, but linger for the history lesson.

Any hotel in San Francisco that has been operating for more than a century certainly has some stories to tell, and the Westin St. Francis is no exception. From socialites to celebrities to politicians, it seems every bold-faced name has slept (or attended late-night soirees) in its Bliss and Faville–designed towers. Today, guests to this distinctive 1,195-room property still enjoy top-notch service with some thoroughly modern touches: The 1904 landmark building recently underwent a $45 million renovation by Dallas-based interior design firm Forest Perkins, inspired by San Francisco’s moniker as “The Paris of the West.” Guest rooms are painted in Parisian blue, goldenrod yellow, and peony pink, and feature original crystal chandeliers. Downstairs, travelers can marvel at the lobby’s master clock—the first example in the western United States—and study a collection of photographs by Ansel Adams depicting the hotel’s long-lost Patent Leather Bar. Pro tip: Let the hotel’s resident historian bend your ear during a historical tour.

In the Orange Walk district, in Northern Belize, lies one of the largest Maya ruins in the country: Lamanai. It is accessible by road but I arrived after a one-hour boat ride up the New River. The name “Lamanai” is roughly translated as “Submerged Crocodile.” Apparently, there was once a thriving population. The ruins may date back to 700 B.C. and estimates put the number of structures, which are part of the ruins, at around 700 buildings; however, less than 5% has actually been excavated. Thick jungle, filled with howler monkeys, birds and jaguars, conceal the remaining structures. The walk through the jungle from the landing dock is certainly evocative. Tall palm trees form a dense ceiling and thick underbrush conceals everything around the path, still littered with pottery shards and artifacts because excavation is still ongoing. The Mask Temple has the most well preserved details but the view from the top of N10-43 (or High Temple) is thrilling. I don’t recommend it for those who are afraid of heights because the climb down is steep and challenging. If you can make it, it’s worth every moment of struggle. I am no expert judge, but I would revisit Lamanai again in a heartbeat; of all the Maya historical places I have been, it was the most interesting and complete in terms of narrative and historical detail. A museum toward the entrance to the complex could easily take an entire afternoon to get through because of the volume of information it houses.