Out Of Town Trips Travel

Puerto Rico Travel Guide // Old San Juan // Part 1

Puerto Rico is a gorgeous Caribbean island southeast of Miami, FL. Some don’t know that it is actually a U.S. territory. Also known as “La Isla del Encanto,” Puerto Rico has a long and rich history, a vibrant culture, a diverse people, and a flavorful cuisine. I’m proud to be 100% Puerto Rican, and I take every chance I can to visit this beautiful island and my family who live there.

This trip was special because it was our first couple’s trip! Lol We went with my husband’s sister and her husband (all of whom are also Puerto Rican). What made this trip extra special was that, aside from myself, none of them had ever really had the chance to explore Old San Juan, visit Casa Bacardí, or hike throughout the Rainforest of El Yunque, etc. We did all that and MORE on this trip and I can’t wait to tell you all about it! For this first part of the travel blog, I’ll focus on exploring Old San Juan.

P.s. Outfit details can be found at the end of the post. 🙂

Everything about Old San Juan (also known as Viejo San Juan) is colorful! From the buildings and landscaping to the culinary experiences and artisan shops. It’s absolutely beautiful! It’s also incredibly charming with its narrow streets paved with cobblestones. Many of these cobblestones that you see and walk on were laid down by early Spanish colonizers and they are a unique shade of blue (note: heels are tough to work with on these just FYI. Hah!) It felt like every little corner we took brought us to a new, wonderful street full of color, Puerto Rican flags, pretty florals, and a sense of history.

On our first day in Old San Juan, we woke up ready to go and explore! But first, food. We visited the Waffle-Era Tea Room and had such a good experience. This little restaurant offers both sweet and savory gourmet waffles that are so tasty. I got the 1/2 waffle serving of the Caneloide (cream cheese, pecans, cinnamon and maple syrup) with a cup of freshly squeezed orange juice and it was insanely good! I don’t drink coffee *gasp*, but they do have a super cool way they make their coffee to replicate traditional Puerto Rican flavor – they brew via fire. Such a unique little spot to try!

After our yummy breakfast, we walked to Parque de las Palomas (Pigeon Park) where you have a beautiful view of the ocean whilst being surrounded by hundreds of friendly pigeons. Lol! You can feed them because there’s always a local selling seeds for a few dollars. Right next to the park is Capilla del Cristo (Chapel of Christ), a historic site and uncommon attraction. This quaint little chapel dates back to the 18th century! Why it was built is a bit mysterious, but it’s lovely to experience none the less.

When you’re in Old San Juan, be sure to stop by Fortaleza Street to see the beautiful umbrella art installation! When we went, all the umbrellas were pink (I think for Women’s History Month), previously they were colorful. Either way, this visual spectacle is a treat to see and gives the street a festive air. Also, it makes for an Instagram worthy shot with the colorful buildings and cobblestone street in the background!  (Note: Unless you get there bright and early, you’ll have to share your shot with others, but that’s ok – it’s still a fun memory!)

Next, we explored San Juan’s famous fort, El Castillo de San Felipe del Morro (aka El Morro). This historical site is a must! From the beautiful architecture to the ingenuity of design, El Morro truly is a fascinating military structure. It was designed to guard and defend the city of San Juan, which was at one time an important port city for the Spaniards. Today, this colonial fortress is an actual piece of history that you are encouraged to admire and explore. Here, you are privy to the most glorious ocean breeze (not necessarily ideal for sunhats and free-flowing hair lol) and the most picturesque view of the ocean. In front of the fort, there is a large green field where you’ll see people picnicking, flying kites, and a few iguanas sunbathing!

After exploring El Morro, we were all starting to get hungry and a bit tired (it’s a lot of walking), so we headed off to find someplace to eat and get re-caffeinated. We decided to stop by Café Cuatro Sombras. What a treat this café was! The atmosphere is really laid back and it was the perfect place to relax a bit and cool off from the sun. My husband and brother-in-law thoroughly enjoyed the coffee and the sweet pastries (they offer savory sandwiches too). The coffee beans used are of high-quality. They use 100% Arabica coffee and it comes from the mountains of Yauco, a city in Puerto Rico – so cool! The aroma in this place was delightful and the service was great. There’s a charming little covered outdoor space where you can enjoy your coffee as well. For the coffee lovers out there, you simply must try this coffeehouse out!

Once we had rested a bit and finished re-caffeinating, we spent some time checking out local artisan shops and souvenir stores – always a fun time – until we came to the last part of our day, which we dedicated to Restaurant Barrachina. This restaurant is the actual birthplace of the piña colada!! Yes, it’s true. And let me tell you, the piña coladas are incredible! I opted for a flank steak sandwich and fries which was so good, but they have a plethora of delicious Spanish and Puerto Rican food options! My hubby opted for a seafood dish that he quite enjoyed. The ambience and atmosphere of Restaurant Barrachina, with the surrounding colonial building and the Spanish-style courtyard adorned with tropical foliage, is such a pleasure, and the culinary experience has always been top notch when I’ve visited. A definite must on your list of places to eat in Puerto Rico.

Phew! Ok that was a glimpse into our first day on the island. It was so much fun exploring and eating our way through Old San Juan! The next day we adventured up to El Yunque Rainforest and then down to Luquillo Beach before having quite an eventful night. More on Day 2 in my next blog post. Stay tuned!! 🙂

Have you ever been to Old San Juan, Puerto Rico? If so, what was your favorite thing to do?? Let me know in the comments below!

Outfit Details: My top is from Loft last season, shorts are Old Navy from Goodwill. My woven sandals are from Discovery. My purse is from Amazon. And my hat is from Amazon too.

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  1. Mirian Mendez says:

    These pictures are beautiful!!!!
    The picture of you and Kiki at “El Morro” brings back lots of our own memories.
    Can’t wait to hear more, lol…

    1. Thank you!! That picture at El Morro is iconic that’s for sure! 😉 Lol

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