Old San Juan, Puerto Rico: An Amazing Discovery

We now realize why Christopher Columbus was in such a hurry to leave the Virgin Islands and continue west. As our "island-hopping" travels continued, a short flight brought us to the other United States Caribbean territory ... Puerto Rico.

For those who don't remember this part of American History class ... Puerto Rico became a U.S. territory through the Treaty of Paris after the Spanish-American War in 1898. 

And that makes another "capital" conquest for me!

We didn't have high expectations when we first decided to spend a week in the capital city of San Juan ... hopefully just enjoy some beautiful weather and eat some delicious seafood while being able to practice our Spanish.

Well, like Columbus, we were about to make an amazing discovery.

Old San Juan's colorful history,

delicious cuisine,

and unique architecture

makes this a "treasure" of a vacation destination!

Discovering Old San Juan's Intriguing History

Christopher Columbus landed on the island of Puerto Rico in November of 1493 and claimed the "rich port" for Spain. The land was settled by the Spanish in 1521, making it the second oldest city in the New World. Because of its strategic location and rich natural resources, San Juan became an important military outpost for Spain during the next 400 years. Castillo San Felipe del Morro and Castillo San Cristobal were built between 1539 and 1790 along with a three mile long wall to surround and protect the entrance of this important island from enemy attacks.

These stone fortresses along with the many historic buildings within the walled city are all a part of the San Juan National Historic Site.

While walking through these two forts,

and around the city that was protected by the wall,

we couldn't help but be amazed at the amount of engineering ingenuity and hard work that went into fortifying this strategically important piece of land.

Discovering Old San Juan's Historic Roots

We took one of the Old San Juan walking tours early in our visit in order to get an insider's perspective on this unique city. As we walked past government buildings, hotels, restaurants, shops, and private homes, I was pleasantly surprised at how the owners have meticulously maintained their residence's historical beauty.

Blue cobble stones dating back to the 17th century still line the streets, although their uneven shifting over time sometimes makes them a challenge to walk or drive on.

These pavers are a result of one of the earliest "recycling" programs. The bricks served as ballast on Spanish ships to help stabilize the vessels, and when they arrived in San Juan, the bricks were re-purposed to pave the streets of the growing city.

Some of my favorite sites while walking along the cobblestone streets of Old San Juan included:

... One of the oldest buildings in the city, the Catedral de San Juan Bautista, which was built in 1521.

... Bright and intimate central gardens/restaurants.

... Whimsical city parks like El Parque de Las Palomas (Pigeon Park) where visitors are actually encouraged to feed the birds. Since they receive plenty of free food here, there are surprisingly very few annoying pigeons hanging out at the many outdoor cafes.

... The Princess Pathway outside of the city walls that was lined with lively outdoor vendors but also provided tranquil views of the harbor.

... Calle de la Fortaleza that leads to the Fortaleza, the stately residence built in the 16th century that now houses the island's governor. According to our tour guide, this street used to be decorated with hundreds of umbrellas, but the city recently changed the decor to glittering lights, much to the dismay of a few locals.

... Paseo del Morro, a two mile path that lies between the ocean and San Juan's historic city walls. Weather, vegetation, and the passage of time continue to chip away at this piece of history even as the National Park Service works to preserve it.

... Fuente Raices, or Fountain of Our Roots, which celebrates Puerto Rico's Indigenous, Spanish, and African heritages that work together for the good of all.

Discovering Old San Juan's Delicious Food

The food scene is bursting with flavor in Old San Juan. The #1 most traditional Puerto Rican dish that every visitor needs to try is the mofongo, which is mashed fried plantains with various fillings such as pork, shrimp, and other seafood.

Tacos are all the rage, and these "crazy shrimp" tacos from Cayo Caribe Restaurant were our favorite. Also popular are the Puerto Rican version of empanadas called empanadillas or pastelillos. They are baked turnovers filled with various meat fillings. And, of course, a meal is not complete without the traditional white rice and bean side dish.

No need to travel to Italy for gelato when Anita's Gelato is just down the street from our Airbnb.  Yes, this was dinner for us one night because after dinner, the line is just too long. 

The closer we get to the equator, the better the coffee. But this peppermint mocha was a bit over the top with sweetness for even Doug's taste ... who would have thought that was possible???

Like other Caribbean islands, food costs are high in Puerto Rico. But we found a bargain on local jumbo shrimp at the neighborhood market. After adding a little garlic, sauteing in butter and serving over rice, for just $6 we enjoyed an easy and delicious restaurant-quality dinner from the comfort of our apartment that overlooked the water.

 Anyone for some classical "crashing waves" dinner music??!!

Discover Old San Juan's Walkability

Puerto Rico suffered devastating damage from Hurricane Maria in 2017, and it was encouraging to see how San Juan's urban and coastal beauty has re-emerged. Our Airbnb apartment was located in the Condado area of San Juan about five miles from Old Town. It, along with many other hotels and condos, was near the sandy beach allowing us to enjoy sunset beach walks and beautiful sounds of waves as they lulled us to sleep. 

We didn't rent a car but were happy to see that, unlike Charlotte Amalie in the Virgin Islands, San Juan is a very pedestrian-friendly city. A wonderful variety of nice beaches, restaurants, and shops were within walking distance of our Airbnb. Ubers are easily available for transport to the airport and into Old San Juan. And as we discovered ... San Juan's bus service is even easier to use, and it's FREE!

Discovering Old San Juan's Gateway to More Adventures

As you can probably tell, we have thoroughly enjoyed all our amazing discoveries during our week in San Juan, Puerto Rico. Its rich history and vibrant culture makes it a fun winter get-away.

 And it is also a convenient gateway to more adventures as we head to the famous "rich port" of San Juan to board a cruise ship headed to the southern Caribbean.

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