I must admit, I love travelling — adventure getaways, relaxing weekends, staycations, and solo, couple or group trips! I learnt over the years that travelling with other women, especially your friends (commonly known as a “girls’ trip”), has becoming increasingly popular among those 25–60.
And as Caribbean Airlines started flying to Puerto Rico recently, four of us decided to go on a seven-day girls’ trip to Old San Juan. We wanted to explore the old city, see what it offered for a combination of fun, relaxation, and a little shopping (a favourite pastime of ours) — as well as what the rest of the island offered for the curious visitor.
Before departure, we diligently did our homework, looking up the best places to say, and what the city had by way of food, culture, and entertainment. We also realised that packing minimally was a real benefit, whether you are going to roam around the cobble stone streets of Old San Juan; venture into the beautiful interior of the island for hiking, ATV riding, or bungee jumping; or simply going to shop (because the shopping is fantastic!).
As we began our descent into Puerto Rico after our three-hour flight on Caribbean Airlines from Port of Spain, we marvelled at the island’s blue shimmering water, lush vegetation, and numerous high-rise buildings.
From the moment we landed at the Luis Muñoz Marín International Airport, we could feel the energy of the place as our excitement built. The people were warm, friendly and accommodating. Our adventure had begun.
Old San Juan — the oldest district of San Juan, Puerto Rico’s capital and largest city — did not disappoint. The drive in felt like we were entering downtown Miami, but with a more serene, alluring, island appeal.
The effervescent, historical city — with vibrant, distinctive buildings dating back to the 16th century — oozed old-world charm, and we were greeted by a lovely Atlantic breeze that provided a respite from the tropical heat.
We stayed at a hotel close to Plaza Colón — near many varied shops, restaurants, and bars, and a few minutes’ walk from the famous Castillo San Cristóbal. Of course, we ventured into as many shops as we could along our street, as well as the other nine or 10 parallel calles that made up this unique, walled city. Walking around, we often felt we were travelling back in time. And if you saw the Netflix series Outlander, you’ll understand what I mean!
Our rooms were nicely appointed, with views of the city rooftops, the castle, and the massive cruise ships that came into port several days we were there. Jacuzzis were available, plus stone bathtubs, where we spent a couple of luxurious evenings after our full days of gallivanting. After all, spoiling yourself is all part of a girls’ trip, isn’t it?
The effervescent, historical city — with vibrant, distinctive buildings dating back to the 16th century — oozed old-world charm
As we explored the city’s restaurants, cafes, and shops, we noticed many offered the typical American-style breakfast, but with some local breads — as most of the visitors appeared to be from the United States. There were also many American chains interspersed with numerous souvenir shops — many providing similar fare, but some showing off unique artisan specialties that tempted us shopaholics.
Each day, we had lunch and dinner at a different restaurant, and could easily have stayed a year without running out of options. Some of the most memorable included two Mexican restaurants on a popular strip called SOFO (south of Calle Fortaleza), Puerto Criollo, El Rincón de Paco (off Calle San Sebastián — a historical gem), and Barrachina (with a lovely courtyard feel and exceptional piña coladas … which is no surprise, given that San Juan is where this delicious drink originated).
A highlight for us was dinner at Triana restaurant, offering tapas and rumba flamenco. Juan Carlos García, the renowned guitarist who accompanied the dancers and who plays at the restaurant most weekends, was exceptional. At 84, his voice and guitar skills did not disappoint. Born in Barcelona, Spain, he grew up in San Juan, and has been featured on the Ed Sullivan Show, played with many famous musicians, and is back home in Puerto Rico having toured the world.
After dinner, we had to sample the late-night pump on the energetic Calle San Sebastián, where all the partying takes place nightly — especially during the annual San Sebastián Street Festival every January (so add that to your bucket list). A popular haunt is La Factoría, but we did not get in, as the line was wrapped around at least two quaint buildings.
So, we settled for a more mellow restaurant, El Tortuga, that offered live salsa, bachata, and other Latin styles of music. Some culinary favourites: Mafongo and everything, mango fish ceviche, spicy crab bowls, and shrimp tacos — but, just so you know, the shrimp comes in soft tacos, while all other offerings came in hard shells. Did not matter, it was delicious!
We delighted in a range of sightseeing across San Juan and beyond, including a visit to the Bacardi factory, where an entertaining tour guide provided the history of the products. Sampling the cocktails and the more expensive rums was a delight.
Of course, when girls get together, shopping is a must, and there are many malls to explore. Plaza Las Américas — the largest in the Caribbean and second largest in Latin America — was the first that we visited, featuring hundreds of popular American shops and brands alongside local ones. We also visited an outlet mall about a half hour away from Old San Juan that had some great bargains (we were lucky enough to be there on an American holiday weekend, which we hadn’t realised until we saw all the great discounts).
We were in awe of the magnificent murals on the walls and sides of huge buildings, all along Calle Cerra in Santurce — another San Juan neighbourhood 10 minutes from Old San Juan, and an unexpected surprise. Some consider it the “capital of art in the Caribbean”.
To cool down and chill, we also went to the nearest little beach in San Juan, Playa Puerta de Tierra — just over the bridge from Old San Juan. It was a lovely day, and we actually walked back to our hotel to take in some of the many sights along the route, despite it taking about an hour.
Old San Juan was wonderful, and we will definitely be back, as it is ideal for girls’ trips, family holidays, and romantic getaways. The only thing that was scarce in some smaller restaurants and even in our hotel was consistent Wi-Fi. But if you are having so much fun in such a beautiful city, who really needs it?