Old San Juan is a town you WANT to get lost in. You can wander the cobblestone streets among the bright, colorful houses for hours without getting bored. There are historical landmarks, amazing restaurants, and great shopping around every corner. Animal lovers can’t help but notice the hundreds of healthy stray cats that roam the city adding to its charming ambiance. Old San Juan is an incredibly romantic place and a trip to Puerto Rico isn’t complete without a visit to this historical city.
We first visited Old San Juan four months ago with our cruising buddies, Will and Cat from Monday Never. We were blown away by its beauty and historical importance. Now that we live only a few miles away, we have visited the city many times since. Each time we discover something new and uncover more of Old San Juan’s history.
Founded in 1509, Old San Juan is the oldest city in the US and its territories. Many of the historical landmarks and buildings in Old San Juan are more than a hundred years older than any historical building found in the United States. Walking the blue cobblestone streets, you feel as though you have been transported back in time. Much of the stunning colonial architecture is still preserved in this walled city. Here are just a few of our favorite things in Old San Juan.
1. La Muralla (City Wall)
One of the first things you’ll notice about Old San Juan is the massive protective wall that surrounds the city. The wall was first constructed in the early 1600’s and was extended as the city continued to grow. It is 3.4 miles long and up to 25 feet thick in some places.
2. Blue Cobblestone Streets
The blue cobblestone streets add to Old San Juan’s romantic ambiance, but these stones are not just decorative. They were used as ballast to stabilize trade ships. The stones were unloaded before the ships were filled with sugar cane that was produced in Puerto Rico.
3. Paseo del Morro Trail
Paseo del Morro is a ¾ mile trail outside of the city wall from the city gate to El Morro Fort. The trail offers stunning views of the city wall, El Morro Fort, and the shoreline. There’s very little shade on this trail, so be sure to wear sunscreen.
4. Castillo San Felipe del Morro (El Morro Fort)
Construction of the fort began in 1539 and it survived many attacks while the island was under Spanish rule. From its first battle against Sir Francis Drake in 1595 to being used by the US military during War World II, there’s a lot of history to discover inside the fort’s walls.
5. The Old San Juan Cats
Cats, cats, and more cats. There are hundreds of cats that roam the streets of Old San Juan. Walking down Paseo del Morro Trail, you’ll see at least a dozen hiding in the bushes or sunning themselves on the rocks. It is said that some of these cats are descendants of the original cats that arrived on Spanish ships. Regardless of their heritage, they are certainly a part of the Old San Juan experience. These cat colonies are controlled, fed, and cared for by the Save-A-Gato volunteer organization. You can learn more about the organization and how you can help the cause here.
6. Santa Maria Magdalena de Pazzis Cemetery
Above ground cemeteries usually give me this heebie-jeebies, but this one sure is beautiful. It’s located outside the El Morro Fort walls on the coast. With a nice ocean breeze and the crashing sound of the waves hitting the rocks below, this is a very peaceful resting place for some of Puerto Rico’s most prominent figures.
7. Brightly Colored Homes and Buildings
Everywhere you turn, you’ll see bright, vibrant colors in Old San Juan. It’s nearly impossible to not smile as you walk down the narrow streets, surrounded by brilliantly colored buildings and homes. It’s crazy to think that this charming city and huge tourist attraction was nearly destroyed. By the late 1940’s, Old San Juan was rundown and dangerous. Anthropologist Ricardo Alegria convinced local authorities to preserve the colonial architecture instead of paving it for new modern designs. The hard work paid off, because today the brightly colored homes and buildings of Old San Juan are admired by all that visit.
8. Capilla del Cristo (Cristo Chapel)
Capilla del Cristo can be found at the end of Cristo Street on top of the wall. From the outside, it’s a small humble chapel, but inside you’ll find a stunning alter made of silver. Legend has it that during a festival celebrating Saint John the Baptist, a young horse racer was unable to stop his horse and went tumbling over the edge of the city wall. He miraculously survived and the chapel was built to celebrate the miracle.
9. Castillo de San Cristobal (San Cristobal Fort)
Built between the years of 1765 and 1783, the San Cristobal Fort is the younger of the two forts in Old San Juan. After its completion, the old city was completely walled-in. In 1897, after nearly a hundred years of peace, about a third of the fortification was removed in order to let traffic in and out of the city. Like El Morro, the San Cristobal Fort saw its last battle during the Spanish-American war in 1898. A few months later, the Treaty of Paris was signed and Puerto Rico became a US territory.
10. Window Shopping on Fortaleza Street
You’ll find art galleries, souvenir shops, restaurants, and high end retail stores lining Fortaleza Street. As cruisers on a budget, most of the shopping we do here is window shopping. However, we love wandering in and out of the art galleries, admiring the work of local artists.
11. The Restaurants
If you are in the mood for a nice dinner, you’ll have a lot of great options in Old San Juan. One of our favorites, La Factoria, is a tapas restaurant. You can get your fill of small plates and fancy cocktails in this multi-bar speak easy.
12. Bahia de San Juan (San Juan Bay)
There’s always something interesting to spot in the San Juan Bay. Massive cruise ships dock here a couple of times a week. When the cruise ships are in town, expect to see outdoor markets and vendors catering to the tourists. Several Fishing and Sailing Charters also work out of the Bay. For us, we just like admiring the different boats.
Even though it lacks beautiful beaches like most of Puerto Rico’s coastal towns (they’re only about 2 miles away), Old San Juan’s history and charm make it a must see destination that shouldn’t be skipped.
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