WATCH: Old San Juan — the Best Quick (and Cheap!) Weekend Getaway

Old San Juan Puerto Rico Weekend Getaway

Just a few hours away from New York City is a history lover’s dream: Old San Juan, Puerto Rico. Founded by the Spanish over 500 years ago, it’s a perfectly preserved time portal. Walk around Castillo San Felipe del Morro, the ancient Spanish fort that surrounds the old city. Inside the walls, ramble through narrow cobblestone streets and past the cathedral (where Dayanara Torres married Marc Anthony) and pick up a piragua — a Puerto Rican snow cone that comes in flavors like passion fruit, mango, and tangerine.

Half the price of Miami and without the club music booming through the streets, Old San Juan is the perfect place to get away from it all — no passport required.

Just watch out for the pigeons. One of the most popular spots in the old city is Plaza de Armas, located up the hill from where the cruise ships park, it is the main point of entry to the old city for many tourists. It is also a pigeon mecca. Thousands of the birds flock there and, despite Puerto Rico having a large cat population, they waddle, sit, and roost unmolested. This would be fine if they also hadn’t gotten into the habit of hanging out, sitting and roosting on people. On any given day, tourists will throw breadcrumbs and turn into living pigeon trees. This is problematic for so, so many reasons, least of which is THEY ARE BASICALLY FLYING RATS! Do you know how many diseased pigeons carry? (answer: LOTS!). That and they have no sphincter muscles so the poop just flies at will. Enter that park at your own risk.


Old San Juan has absolutely everything you need for the perfect getaway. (Photo: ABA Staff)

Here’s everything you need to know to do the city properly.

Warning: From 11 a.m. to 3 p.m., the cruise ships hit and certain areas of the old city are packed with cruisers. Hit the shops before or after this time to avoid a massive headache.

Stay: Hotel El Convento, the Chateau Marmont of the Caribbean. Housed in a former convent, the rooms surround an inner terrace with huge trees. The rooftop pool offers some of the best views in the city, and the restaurant is legendary.

Shop: Ole Curiosidades. This famous hat store lets you get measured, pick your ribbon color, and walk out with a personally fitted, handmade Panama-style hat for around $70 — three times less than almost anywhere else in the world.


This was not the first hat that Paula tried on.

Eat: Café Don Ruiz. Serving some of the best café con leche and Pan de Mallorca, a specialty sandwich with ham and cheese, this café grows its own coffee and roasts it in the back. These baristas are artists.

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Drink: La Factoria. The bartenders here elevate mixology to a high art. Each drink is mixed to perfection and includes syrups, mixes, and extracts made in-house. Hungry? The bar snacks are just as good as the drinks. Try the fried goat cheese with lavender-infused honey. Bonus: Across the street is a dance studio, so you get live entertainment.

Food tour: Spoon Food Tours. Make sure to ask for Carolina Johnson. These people know Old San Juan like the back of their hands and will tell you everything there is to know about street food and local restaurants, bars, and culture.

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