Hola viajeros! My name is Alli Wren Martin. I’m a food, travel and wellness blogger based out of Austin, Texas. I will be sharing my experiences in the colorful Old San Juan which is one of the crown jewels of Puerto Rico.
My love for travel began in my early twenties, but for reasons you might not expect. I grew up in an abusive household where I lived in fear. Fast forward to adulthood, and my trauma-based anxiety and depression kicked into full gear. I knew I had to do something to change course, so I started traveling.
A Wonderful Trip to Puerto Rico
Puerto Rico is a beach paradise alive with a rich history and vibrant neighborhoods – what more could you want?! As we all know, COVID border closures limited travel during quarantine. Once I got vaccinated, that presented an opportunity to explore all of the amazing places the US and its territories had to offer. Puerto Rico was at the top of my list.
I wandered around Old San Juan’s blue-toned, cobblestone streets laced with beautifully-colored buildings. I hiked through the gorgeous, lush green El Yunque Forest and slid down its waterfalls. I laid out in the sun on their breathtaking beaches with clear, turquoise waters and white sand. All the while, I ate some fantastic local Puerto Rican food including alcapurrias, mofongo, carne frita, tostones and jibarito. It was a fantastic trip!
I spent a week in San Juan in various parts of town, three of which were spent in Old San Juan. The architecture of Old San Juan was awesome to learn about and the food was top notch! However, my absolute favorite part of Old San Juan was the locals. Everyone I came across was so genuinely open, friendly and helpful in their recommendations. I made a lot of new friends there that I’m still in touch with to this day.
The Rich History of Old San Juan
I was lucky to be shown around Old San Juan by an amazing guide who has lived in San Juan for his entire life (more about that experience and my recommendations below). There is so much rich history about the Old San Juan district that is tied to its architecture and to Puerto Rican culture.
Old San Juan is the oldest city in the US and its territories. Walking through the district, it’s evident that the architecture is a mix of various cultural and artistic influences, which reflects Puerto Rico’s dynamic and complex history. You will find different architectural styles around each new corner – from beautiful Baroque to Spanish Colonial, Gothic and Neoclassical styles.
The Spanish explorer Juan Ponce de Leon (known for searching for the fountain of youth) founded it in 1519. He resided in the oldest home in San Juan called Casa Blanca (more like a castle fort) built by his son-in-law.
San Juan eventually became a Spanish military outpost and thriving port city, after it was simply a frontier community. Spanish fleets would stop here to haul gold and resources back to Spain. Old San Juan was originally named “Puerto Rico”, which means “rich port” in Spanish.
Puerto Rico remained Spain’s province until the Spanish-American War, which subsequently led to it becoming a U.S. territory. As you stroll through the downtown area of Old San Juan, you can sense the level of history here – showcased in the historic sites, cobblestone streets and colorful buildings.
6 Best Things To Do in Old San Juan
1. Enjoy the Views at La Garita Yaz Restaurant & Bar
My favorite place in Old San Juan was the patio at La Garita Yaz, a local restaurant and bar. It overlooks La Perla’s colorful buildings and the crystal-clear ocean. I sat here for the longest time gazing out at this incredible view. It was wonderful to kick back with a beer and enjoy the ocean breeze and the beautiful landscapes. I highly recommend La Garita Yaz!
2. Walk around the Colorful Streets of Old San Juan
One of the best things to do in Old San Juan is walking around and taking in the sights! You will see all of the colorful buildings, blue cobblestone streets, promenades, colonial churches and other historic sites.
3. Try the Local Puerto Rican Food and Drinks
Puerto Ricans are really proud of their food (as they should be)! Here is your local food checklist of must-trys: mofongo, alcapurrias, tostones, carne frita, ceviche and jibarito. Out of all Puerto Rican restaurants in Old San Juan, most locals recommended El Jibarito in the center of Old San Juan. As one local said: “If you are looking for pure Puerto Rican food, this place is it”!
For drinks, Puerto Ricans love their rum. Try out locally made, small batch rum at Scryer Rum distillery – which is located in the heart of Old San Juan. Also, did you know that San Juan is the birthplace of the pina colada? It’s Puerto Rico’s national drink, so be sure to have a few while you are there.
4. Take a Guided Walking Tour of Old San Juan
Old San Juan is filled with history that sets it apart from other Caribbean destinations. Without a guided tour, it would be difficult to scratch the surface of the significance of its architecture and history. The Old San Juan Best Kept Secrets Tour uncovers the hidden details of this historic district.
Andy, the tour guide, was born and raised in San Juan and has lived there for over 60 years. This is a steal of a tour ($25 on Airbnb)! There are so many unique elements that I would have never noticed if it weren’t for this tour.
5. Explore Old San Juan’s Historic Fortresses
Seeing the old city walls of Castillo San Cristobal and El Morro is an absolute must. Travel back in time to the Spanish colonial era when these defensive structures were built to protect against land-based attacks. There is a small admission fee ($7 gets you into both Castillo San Cristobal and El Morro).
6. Watch the Sunset along the Paseo de la Princesa
Paseo de la Princesa is a gorgeous, tree-lined promenade in Old San Juan sprinkled with beautiful fountains and sculptures. It’s the perfect place to watch a Caribbean sunset while having some tasty Puerto Rican gelato!
My Best Experience in Old San Juan
My best memory from Old San Juan was mingling with locals at Scryer Rum. In addition to having masterfully made cocktails at their bar and patio balcony, I had some of the best conversations there. I got an inside look at what it was like to live in Puerto Rico. The locals in San Juan are so friendly, open and helpful. And I loved that this bar wasn’t a tourist trap!
Where to Stay in Old San Juan
Power outages are more common in Puerto Rico than you might see in the contiguous US. In fact, a blackout happened during my stay! I was lucky and it only lasted a few hours. However, according to locals, they can last for days at a time. Not to worry, hotels and airports have back-up generators. However, if you are in an Airbnb, you might be out of luck during a blackout. This is just something to consider when booking your stay.
As a solo traveler, I stayed in the CasaBlanca Hotel which was in the center of Old San Juan and was walking distance to everything. I found this hotel to be of great value. The lobby is gorgeous and it has good air conditioning throughout. It also had extra amenities like hot tubs and a rooftop terrace.
If you are looking for something more economical, I would suggest Fortel Hostel – a highly rated hostel in the Old San Juan district. It has everything you need and is well-designed and recently remodeled. Most importantly, it’s located in the heart of the old city. Prices there start at $35!
If you are all about luxury and unique experiences, I highly recommend Hotel El Convento. It’s a luxurious stay that is distinctively located in a former 16th century convent! This hotel is a landmark treasure, a member of Historic Hotels of America and Small Luxury Hotels of the World.
352 Guest House is another brilliant stay but this time for families! It’s a boutique bed & breakfast that has spacious family rooms. And it’s in a superb location, walking distance to everything in Old San Juan.
Need to Know Before you Go
- A lot of things are closed on Mondays and Tuesdays, so plan accordingly. In the words of one of my local friends: “We party Wednesday to Sunday, and do our chores on Mondays and Tuesdays.”
- La Perla travel advice: La Perla is a historic barrio that is not as safe as the rest of the city. If you go, be sure to follow the rules of the neighborhood, don’t take pictures of anything, don’t go at night and definitely bring a couple of friends or locals along with you.
- The blue cobblestone streets within the district can get slippery, especially when it rains. Wear good walking shoes with some traction!