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Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

The Heladería de Lares, a 45-year-old family business, sells about 50 unusual flavors of ice cream up in the mountains. Salvador Berreto, known to the locals as Yinyo, founded the shop to commemorate the Grito de Lares, a battle for freedom that had taken place exactly one century before. Yinyo started with corn, a flavor at the heart of the Puerto Rican diet and the current bestseller. Other flavors are cod, coquito (the Puerto Rican version of eggnog), and rice and beans. Fortunately, you can taste two flavors before deciding what to buy, and the ice cream is cheap, so you can stock up. Every weekend, people form what locals like to call lines, but are really boisterous blobs extending half a block down from the shop’s entrance. While eating, people skim through newspaper clips about when Denise Quiñones, a girl from Lares, won a Miss Universe pageant, or study photos of the 1945 Fuego de la Candelaria (a fire in Lares). After reading about the history behind Lares’s anthem and running their hands over the guiro (a musical instrument played by scraping its serrated surface), people often wander outside to the Plaza de la Revolucion. Here, on a typical Sunday, artisans sell paintings of the three magi (the Puerto Ricans’ second Santa) and of flamboyanes (the national trees with orange flowers). If you have doubts as to whether it’s worth it, just ask Bill Clinton and his daughter Chelsea. In 2008, Clinton forced $100 into the hands of Yinyo’s son for a mango ice cream.

This novel walking tour combines a power work-out with sightseeing. You’ll climb a steep hill to reach a look-out spot with sweeping views of Vallarta and Banderas Bay, then descend to see Elizabeth Taylor’s and Richard Burton’s former homes (and the bridge that connected them), a tortilla factory, Cuale gardens, and a chocolate shop. Lots of samples and healthy snacks are included, as are plenty of photo ops.

Have you been here? Tell us about it below!End your day in Old San Juan with a pre-dinner stroll along the water, alongside the Old City Walls. It’s that time of day when everything seems to slow down, even the waters of the Caribbean Sea begin to ease into a glassy stillness - perfectly reflecting the midnight blue sky and the incandescent glow of the street lamps. Start from Paseo de la Princesa, at the Raices Fountain, and wind your way around the walls. Take in the views of the setting sun from the benches that line the walkway. Reminisce about the day and linger. There’s no need to rush into the night and tomorrow will come soon enough.

Esperanza is located on the southern side of Vieques island with a laid-back vibe reminiscent of Key West. This small town has an main street that runs parallel to the ocean called “El Malecón” that is dotted with friendly guest houses, funky bars and even gourmet restaurants. It makes a great base for exploring the island’s treasures: it’s walking distance to Playa Esperanza and Sun Bay and only a 10-20 minute drive to the secluded beaches in the wildlife refuge.

This sleek outdoor mall sits in the lavish neighborhood of Puerto Cancún, known for its marinas, golf course, and luxury homes. The shopping center features international brands like Zara and Sephora, along with a stylish, upscale food court featuring its own bar, views of the marina, and cuisine from all over the globe (think Thai fusion, raw bar, gourmet burgers, French bistro, sushi). For entertainment, the expansive Cinépolis movie theater has a VIP section with cozy recliners and table service right to your theater seat. Though designed for tourists, the theater is popular with local crowds, as well, thanks to its convenient location between the Hotel Zone and downtown. On weekends you can catch performances throughout the mall, including live music and acrobatic shows.

Cuevas del Indios (Indian Caves) of Arecibo offers a tidbit of ancient history of a lost people. An easy-to-find natural wonder, with a simple $2 fee for parking, this you won’t want to miss. Bring some sunscreen and your camera. Begin your hike up sharp and spiky cliff sides (no worries, I was able to do it all in sandals). Work your way up to the top of the cliff and enjoy the fantastic view below. Ocean spray from the massive waves breaking against the side of the rocks will cool you off with a little salty mist. Dare to look over the edge to see a landscape of arches and tunnels, burrowed below your feet. Climb down into the rocks to find a wonderful—and surprisingly well-preserved—variety of Taino Indian petroglyphs. A small climb down a somewhat sturdy, handmade ladder lands you at the base of the cave with stone carved images surrounding you. Now is your chance to experience some history. Wander through the smaller tunnels, and listen to the ocean making its way inside the cave with every massive wave crashing outside.

Puerto Vallarta’s “Zona Romantica,” or “Romantic Zone” has all the elements that make the neighborhood name a fitting one: cobblestone streets, proximity to the beach and its stunning sunsets, and plenty of shops, restaurants, cafes, and bars, some with live music. One of the most picturesque sights is the Church of Our Lady of Guadalupe. Instead of a cross-topped steeple, the church impresses with its filigree crown. Walking without a destination is just fine in this safe part of the city, full of lovely views.

In the area of the Norman palace, near the market, there are still some little medieval botteghe (shops) below the level of the palace. Via dei Biscottari is where they used to make the pastries and cookies for the king. There is one shop I love to visit where they still make the shells for cannoli by hand. Sicilians love cannoli, of course, filled with fresh ricotta. We have an intense sweet tooth. Via dei Biscottari near Via Saladino

Along with stylish boutiques and design shops, the narrow lanes of the upscale Khan Market are lined with all manner of eateries, from cafés and cocktail bars to food stalls and fusions restaurants. As of late 2018, the roster also includes Sly Granny, which arrived on a wave of buzz generated from its original Bengaluru location. Through this often-packed bi-level outpost is smaller than the sprawling first location, the concept here is the same: a space “inherited” from a mythical globetrotting grandmother and inspired by her favorite recipes and eclectic style. Here, that translates to a décor of plush velvet sofas, old cookbooks, and crystal bric-a-brac, statement tableware, and bold, quirky artwork in the snug dining room, plus a cozy upstairs bar that converts to a cocktail lounge come dark. Drinks there range from the creative (crafted with ingredients like elderflower, yogurt, or honey-ginger syrup) to the classic (twists on G&Ts and Pimm’s cups), not unlike the style of the food menu below, which starts with pastas, steaks, and burgers, then veers towards tacos, schnitzel, chicken liver pâté, and Kerala-style fish moilee. You won’t need a granny’s encouragement to eat up dishes like bacon-gruyere mac-and-cheese balls, house-cured salmon, chocolate lava cake, and a twist on grilled cheese with ricotta, onion jam, tomato chutney, and two kinds of chilies.

La Isla de Guilligan (Gilligan’s Island, though not the one from the television show) is a popular hangout for Puerto Rican locals. I myself am only home for several weeks a year and I still go once or twice every year. The island is sometimes isolated and sometimes crowded. It boasts snorkeling (I’ve spotted many anemones, fish, crabs, starfish, and barracudas), calm water perfect for floating and swimming, and several trees from which you can jump into the water. It’s off the coast of Guanica, and there are two ways to get there. Either take a ferry (call 787-821-5706 for more information) or rent a kayak from Mary Lee’s by the Sea. If you choose to do the latter, you might want to take your kayak to Isla Ballena (see my highlight “Kayaking and Snorkeling and Hoping for Whales”). This tends to be a day trip, so I suggest you have some food. You can either pack up your own or, if you take the ferry, place an order before embarking and tell them when you’d like to have it delivered. There are picnic pavilions that you can claim if it’s a calm day or you get there early.

A beautiful drive through the mountainous west coast past the bayside city of Mayaguez opens up to windy roads lined with banana trees. Your destination is the coffee town of Maricao—a small, unassuming city that plays host to festivals, coffee tours, and aquaculture. Also the home to the hidden gem of Salto Curet waterfall. To get down to your starting point, a car with 4x4 is preferred but not always necessary (Going during the rainy season? Drive a truck or SUV). You’ll park in a vacant lot at the bottom of a hill and follow the trail over a river and up the mountain. You’ll eventually reach an abandoned ranger station; at that point you’ll turn left and trek up river. Just a short distance later is the isolated waterfall. Take a swim in the cool water, or hunt down the even smaller trail off to the left that takes you up the rocks to the higher and more roaring waterfall above. This is my most loved waterfall site. It’s secluded and never sees many guests at one time. Bring your camera and a waterproof bag, as it’s likely you will be caught in the rain. It is a rainforest, after all!

Seattle’s most iconic restaurant has earned its laurels, reinterpreting Pacific Northwest classics like bonito with chrysanthemum and sea bean caper, and ricotta dumplings with mustard, rapini, and stinging nettles. in 2015, a young hotshot took the helm: Brady Williams, formerly from the two-Michelin-star Blanca in Brooklyn, New York. He ditched his goal of playing professional hockey to cook—and, boy, has it paid off! Among other distinctions, he was anointed a finalist for Rising Star Chef of 2017 by the James Beard Foundation (the year it won “Best Wine Program”). Reserve ahead and break out the grown-up clothes to check out his masterpieces, served high on Queen Anne hill overlooking the seaplanes and sailboats gliding on Lake Union.

The Red Door Boutique is a relatively new gift shop to Rincon. You can find all sorts of handmade crafts and upscale items for host gifts or trinkets for yourself. Nautical and island themed, this is a great place to find something out of the ordinary—not your typical souvenir. The shop stays open most days during the tourist season (Nov - Apr) and sporadically during the off-season, like many other places around town.

“Seattle’s best happy hour” is not a title to be bestowed lightly, but List has more than its share of devotees. And with good reason: their happy hour features half off the food menu, plus discounted beer and wine. List serves Italian food with a focus on seafood, and it’s an excellent value at happy hour. We loved the gnocchi with black truffle cream, spicy meatballs, and cannelloni with spinach and ricotta. Unsurprisingly, List fills up quickly on the weekends, but if you stop by early, you can settle in, admire the modern decor and striking red chandeliers, and watch the plates pile up with delicious deals. Their happy hour is all day Sunday and Monday, and 4 to 6:30 p.m. Tuesday through Saturday (with a late happy hour Tuesday through Thursday from 9 to midnight).