LP Local Melissa Alvarado Sierra was born and raised in Puerto Rico. After traveling to different countries, mostly aboard a sailboat, she decided to settle in Borinquen and write about its wonders. Now you can find her driving through dirt roads that lead to hidden swathes of sand in Vieques, eating alcapurrias in a beach shack in Loíza, or hiking the impossibly lush El Yunque rainforest in Rio Grande.

She likes to carry a moleskin notebook with her while she explores and tends to stop abruptly to record her impressions. Those walking behind her usually bump into her – it’s a good conversation starter.

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The view of San Juan from the water is spectacular © John and Tina Reid / Getty Images

When I have friends in town… we go sailing in the San Juan Bay. This unique vantage point highlights the colonial buildings of the old city, the people roaming the streets and the almost 500-year-old fort. Seeing everything from the water gives a wonderful sense of place and helps people enjoy the town even more when they discover it on foot. These sailing trips are easy to come by – several touring companies, like Sail San Juan Bay, offer excursions into the waters surrounding the city. I also like to take friends on a food tour of my own design in Old San Juan, always stopping at Casa Cortés for hot chocolate with rum, at Princesa Gastro Bar for shark bites and coconut rice, and at Pirilo for ground beef and plantain pizza.

When I’m up for a big night out… we head to Calle Loíza and drink our way through all the cool and quirky bars in this area, like Bar Bero, where you can get a drink and a haircut, or La Junta, where you can dance salsa gorda all night long. Bonus: this popular street is also home to some of the best eateries in San Juan. When hunger strikes, we usually stop at Loiza 2050 for coconut crusted pizza or at Tresbé for some killer veggie sliders.

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LP Local Melissa Alvarado Sierra takes a stroll down Calle Loíza in San Juan © Melissa Alvarado Sierra

A typical weekend involves… getting mayorcas and a cup of café con leche in the morning at La Bombonera on San Francisco street, walking to Caleta de Las Monjas to watch the ships come into the bay, and later grabbing ice cream at Señor Paleta. Afternoons are usually spent drinking wine and listening to jazz at Carli’s Fine Bistro on Tetuán street, the restaurant of former Beach Boys pianist Carli Muñoz.

Talk a walk down Caleta de las Monjas to watch ships come in to San Juan ©

I have a dog… and I take him to Ocean Park beach to play with other pups in the sand, or we run from Old San Juan to Condado via the new oceanfront pathway for pedestrians. For pet-friendly restaurants, we go to Kamoli in Calle Loíza, the Miramar Food Truck Park in Miramar, or Freshmart in Condado.

For cheap eats… I go to Piñones in Loíza, an area with dozens of food kiosks and restaurants serving delicious fried food and seafood by the ocean. I usually grab a bite and then walk by the beach for a little while; it’s a great way to disconnect from the city’s hullabaloo. Another favorite of mine is La Casita Blanca in Santurce, where they whip up truly authentic Puerto Rican food in an atmospheric space at very affordable prices.

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Alcapurrias are a Puerto Rican specialty ©

One thing I hate about San Juan is… the driving, which can get a little difficult because of heavy traffic during late afternoons.

For my 30th birthday I celebrated at… a beach in Condado. We had a late night picnic by the ocean, sang birthday tunes, and laid back to watch and count the stars. Nothing fancy, but definitely unforgettable.

When I want to go out alone, I visit… museums. San Juan has many amazing museums focused on different themes, from contemporary arts to maritime history, and all are quite accessible and affordable. I also love going to Fine Arts Cinema and ordering a glass of pinot grigio to drink while I watch a foreign or independent film – to me it’s one of the most luxurious and self-loving things to do in San Juan, besides doing paddle yoga and meditation in the Condado lagoon, of course.

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Enjoy a sunset paddle on San Juan's Condado Lagoon © Dennisvdw / Getty Images

When I want to get out of the city… I go to the west side of the island. My siblings live close to Rincón, and I love staying with them and hitting the beach. It's a surfer’s paradise, but also a great place to unwind. The food truck frenzy made its way into Rincón and now there are many healthy options available, and the spirit scene is similarly alive and well. A little wine bar called Tinto, run by sommelier Nassine Campos, carries a wonderful array of wines – I especially love their Portuguese reds. If you're more of a beer lover, head to Rincón Beer Company, where you can play Connect Four with your friends while sipping on hand-crafted brews, including their delicious mango beer.

I know I’m a San Juanera because… I enjoy every corner of this wonderful city, be it the posh side of Condado or the up-and-coming sector of Santurce. I believe in the youths who are stepping up to the plate by starting their own businesses and offering quality products and services that are making San Juan one of the most exciting cities to visit in the world. It’s a great time to be in San Juan!

Need more city travel inspiration? Check out The Cities Book, a celebration of 200 of the world’s great cities, beautifully photographed and packed with trip advice and recommendations.

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