We stayed in an Airbnb on Calle San Francisco, right in the heart of Old San Juan, and it turned out to be an excellent base, especially for a first visit to Puerto Rico. Everything is close by. Beaches within walking distance, a wide selection of restaurants, bars, and cafés, and a neighborhood that’s easy to navigate on foot. Prices are generally higher here than elsewhere on the island, and the most popular restaurants often have long lines, which can make getting a table a challenge, but the location more than makes up for it.
Old San Juan is also the most compact part of the city. The neighborhood sits on a small peninsula, surrounded by the sea on three sides, and is made up of narrow cobblestone streets, colorful colonial buildings, and massive fortifications that reflect Spain’s early presence in the Caribbean.
Founded in the early 1500s, Old San Juan served for centuries as a strategic hub for trade and defense. That history is still clearly visible in the cityscape, where the large forts frame the town and overlook the ocean. Inside the walls, the pace shifts. Streets are narrow, buildings stand close together, and the area is best experienced on foot.
Today, Old San Juan is a mix of everyday life and tourism. Locals still live here, but many businesses cater to the cruise ship passengers who arrive daily at the port. As a result, the neighborhood changes character throughout the day. Early mornings and late afternoons are calmer, while midday can feel crowded and intense, especially when several large ships are in port at the same time.
The architecture is a big part of the appeal. Houses are painted in bold colors, balconies are narrow, and small plazas, churches, and hidden courtyards appear if you take the time to look for them. It’s a neighborhood that invites slow exploration, with breaks along the way for coffee, something cold to drink, or a bite to eat. Distances are short, the ocean is never far from view, and even when the streets are busy, the area still feels manageable. It’s the combination of history, scale, and setting that makes it easy to settle into life in Old San Juan.
