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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.

“Everyone from the late blues musician Stevie Ray Vaughan to the Butthole Surfers has played at the Continental Club. Musicians who do big gigs in Austin like to play small shows here afterward,” says Liz Lambert.

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.

Part cigar store, part bar, and part lounge: Corona Cigar Company is pretty much cigar nirvana for some. With indoor and outdoor seating, including sumptuous leather and wood chairs, this is a chilled spot for a smoke and a drink. Go before a movie or after dinner at the Colonial Town Park.

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.)

A who-knows-how-happily-married Diego Rivera commissioned this three-residence compound from Mexican artist and architect Juan O’Gorman in 1931. Jarringly Bauhausian for its time (especially in comparison to the surrounding San Ángel neighborhood’s mission revival gentility), it included separate buildings for Diego and his wife, Frida Kahlo, connected by a slender bridge (as well as a third dwelling for O’Gorman). Visits lead to interiors, showcasing Rivera’s studio and its fascinating collection of artworks, creative infrastructure, and amazing windows. Take time to wander the garden and pause to appreciate the property’s tableaux; then re-tox from all the aesthetic purity across the road at the San Ángel Inn, a gloriously indulgent hacienda bar and restaurant that takes you straight back to the country club—flawless margaritas and all.

Many temptations are under one roof at the Langham, New York, Fifth Avenue. This polished hotel bucks the trend of tiny Midtown hotel rooms with spaces that begin at 420 square feet and stretch up to apartment-style accommodations with full kitchens—an ideal setup for families. The style is modern and refined, from the sweeping staircase that connects the lobby to the Michelin-rated Ai Fiori restaurant of chef Michael White on the second floor. The hotel doubles as an art gallery for the work of American artist Alex Katz, whose bold figurative paintings hang on the walls throughout the hotel. There’s also Chuan Body + Soul, a day spa based on the principles of Chinese Medicine.

San Juan Cemetery lies on the coast adjacent to El Morro (San Juan’s beloved fort) and nestled in the district La Perla, a rougher part of town. Its statues and tombs make it as beautiful as a New Orleans cemetery. Exiting El Morro, head down the grassy field to your left to catch this flustering overhead view. On this day, a powerful storm was rolling in, casting everything in gray.

Stop at Scribe Winery and pick up a bottle of their newly released rosé to pair with oysters at Hog Island in Marshall, CA. Picnic tables overlook Tomales Bay and must be reserved in advance. Throw the oysters on the grill or eat them raw and don’t hesitate to ask the staff to share shucking tips. This appeared in the May 2014 issue.

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.

Whether you’re a frequent flier or a first time traveler, Red Oxx bags and luggage will outfit your exploration with style. Red Oxx carries a multitude of high quality bags and suitcases specifically designed for whatever adventure you’re about to embark upon, whether it be a wild African safari or a business meeting a state away. Safari bags, expedition bags, day packs, briefcases and garment bags are just a few of their products; all hand made in Montana.