A Day in Historic San Juan

During my recent Dinogo cruise, one of the stops was San Juan, Puerto Rico. It was my first visit to this beautiful island, and I was thrilled to spend an entire day discovering the charm of this historic city.

Although there were numerous exciting excursions available, my friend Suzie and I were particularly keen on exploring some restaurants recommended by friends on Facebook and Twitter. Using Dinogo’s wifi, we downloaded a map and a self-guided walking tour of San Juan and reached out to our social media friends for tips on sights and activities. Their fantastic suggestions allowed us to create a delightful day filled with delicious meals, beautiful views, and a little shopping.

Our planned activities for the day:

MORNING

Our first stop was for coffee at Cafe Cuatro Sombras, a recommendation from my friend Julie, who once lived in San Juan. Knowing my passion for quality coffee, she suggested this charming café that serves exquisite artisan coffee made from beans grown and roasted locally on the island.

As we stepped into the café, the rich, nutty aroma of freshly roasted coffee was invigorating, waking us up before we even took our first sip. With a microroaster in the center of the space, the relaxed farm-to-table atmosphere was the ideal way to kick off our morning. We savored a couple of cappuccinos and nibbled on guava sticks—tangy cookies reminiscent of shortbread but made with guava.

After enjoying our coffee, we set off on a walking tour through the charming cobblestone streets and vibrant historic buildings of Old San Juan. I was pleasantly surprised to discover the European ambiance of this quaint city, beautifully complemented by its lively Caribbean spirit.

One of our first picturesque stops was Parque de las Palomas, affectionately known as “pigeon park.” Once the main square of the city, it has become a favorite spot for locals to unwind with the morning newspaper, stroll with their dogs, or enjoy ice cream from nearby street vendors.

AFTERNOON

Not far from Parque de las Palomas is a restaurant called La Barrachina, where we decided to have lunch. We had seen numerous recommendations on social media to visit this iconic spot, renowned for being the birthplace of the piña colada, making it an essential stop on our itinerary.

Their specialty is authentic Puerto Rican cuisine, so we decided to order a sampler plate known as Puerto Rican Delights, which allowed us to savor a variety of dishes including surtidos de frituras (savory turnovers), sorullitos de maíz (corn fritters), and pastelillos de carne y pollo (croquettes filled with beef and chicken). Naturally, we couldn't resist trying one of their famous piña coladas as well.

We also enjoyed a side of fried plantains, which are quite similar to bananas. We chose two varieties: tostones and maduros. Tostones are unripe plantains that are smashed into chips and then pan-fried, offering a potato-like flavor and usually served with a garlic sauce or a creamy ketchup-mayo dip. Maduros, on the other hand, are ripe plantains that are also pan-fried, giving them a taste similar to sweet sautéed bananas. The key difference is one is savory while the other is sweet. Make sure to try both!

For dessert, we shared a coconut flan (a type of egg custard) and a tres leches cake (a rich, creamy cake), along with two more cups of coffee because I can never get enough of it!

After lunch, we resumed our self-guided exploration, heading to Paseo de la Princesa and following the city wall along a path called Paseo del Morro. The walk is approximately 3/4 of a mile long, but the stunning views and photo opportunities made it worthwhile (and a bit of exercise felt good after such a hearty meal). Here’s a glimpse of what we encountered along the trail:

Near the end of our walk, we encountered an ancient city gate that leads back into Old San Juan. Walking through it is quite an experience, as you can truly appreciate the impressive thickness and height of the city wall, which is made of 15 feet of solid stone.

Once we passed through the gate, we were delighted to discover a street vendor selling piragua, a delicious treat made of shaved ice topped with tropical-flavored syrups such as guava, guanabana, and coconut.

Naturally, we couldn’t resist getting one. Who can say no to a second dessert? Plus, it was a refreshing treat in the warm tropical climate.

As we enjoyed our piraguas, we strolled along a charming tree-lined street towards the San Juan Cathedral. On our way, we came across a delightful artist loft named Tres Mujeres, where three talented women craft vibrant handmade items featuring needlepoint designs that showcase scenes from Old San Juan. What I found particularly special about Tres Mujeres is how these local handicrafts vividly represent Puerto Rican life and history in a colorful manner.

As we reached the top of the hill and turned a corner, we were greeted by a breathtaking view of the old fort and graveyard with the ocean stretching out behind them.

With the day coming to a close, we retraced our steps through the cobblestone streets towards the port to board our Dinogo ship, pausing at several artisan shops along the way to collect some souvenirs.