There are plenty of reasons to visit San Juan, Puerto Rico. Inviting blue waters on tropical beaches, ziplines, rum distilleries, casinos, bustling nightlife, amazing food, and a bioluminescent bay are enough to fill just about any travel itinerary to Puerto Rico. But perhaps the most memorable part of our entire visit was a self-guided walking tour of Old San Juan.

We could have easily spent the entire week at the San Juan Marriott Resort and Stellaris Casino and considered the trip a colossal success. However, we wanted to get out and explore the local culture. So we called for a cab and ventured into Old San Juan, which is located on a narrow island approximately two miles long.

The traffic was miserably slow and we were getting hungry. As we crossed the bridge, we asked the cab driver for suggestions of places to experience authentic Puerto Rican cuisine. He said that his favorite place, La Bombonera (one of the oldest restaurants in Puerto Rico), was rumored to be closing after 110 years of continuous operation. He told us that he could drive us there in about ten minutes, or we could walk and be there in three. Needless to say, we opted to walk.

Viewfinder Tip: Wear a white shirt if you plan on eating mallorcas. It will hide the powdered sugar that you are destined to get all over it.

La Bombonera has the retro feel of an old school diner with a long narrow row of counter seats and tables on a ceramic tile floor. At our cabbie’s suggestion, we each ordered a mallorca, which is a ham, egg, and cheese sandwich served on a flakey pastry and topped with powdered sugar. It was amazingly delicious and now sits firmly among the top 10 sandwiches encountered in our travels.

After brunch, we meandered along the blue-gray cobblestone streets towards the far end of the island without any real agenda. It wasn’t long before we happened upon Parque de las Palomas (Pigeon Park). We could actually hear the pigeons before we arrived. The park is located near the Cristo Chapel and features some spectacular pigeon-filled trees with intertwined and twisted trunks and limbs. The backside of the park is bordered by a large rock wall with a number of square cubby holes that the pigeons have claimed as their homes. Though the park offers breathtaking views of San Juan Bay, we didn’t linger long for fear of being pelted with pigeon poop.

Next we headed to Castillo San Felipe del Morro, one of the most popular tourist attractions in San Juan. Located on the Northwest corner of the island at the intersection of the Atlantic Ocean and San Juan Bay, this 16th century fort is a photographer’s dream, offering some of the most phenomenal views in all of Puerto Rico. With tide waters crashing against the sea walls, the fort looked like something right out of a Hollywood set. We were fortunate enough to witness a reenactment of a military unit in period costumes loading and firing a cannon. They weren’t kidding when they told us to cover our ears!

From the fort we saw the magnificent Santa María Magdalena de Pazzis Cemetery and decided to make that the next stop on our walking tour. Our walk took us past scores of kite-flying locals enjoying their afternoon in the long grassy field that is adjacent to the fort and the cemetery which serves as the final resting place of some of Puerto Rico’s most prominent residents. Cemeteries can sometimes be creepy, but not this one. With magnificent statues, ornate grave markers, and the coastline as a backdrop, it is easily the most beautiful cemetery we’ve ever visited.


After about 30 minutes of wandering around the cemetery, it was once again time to eat. We headed back towards the center of Old San Juan, via a maze of narrow streets past local residences, giving us a nice glimpse of how some of the locals live. When we got back into a more commercial area, we checked out the menus and prices of several restaurants before deciding on Toro Salao. While we had to wait a few minutes for a table, the paella and empanadas were well worth it.

Having eaten perhaps a bit more than we should, we felt it best to walk back to the resort to burn some calories. We were probably no more than three blocks away from the restaurant when it began pouring down rain. So we ducked into a nearby casino where we made a donation while waiting for the rain to pass. The rain lasted longer than we had hoped so with lighter wallets and heavier waists, we ended up taking a cab back to the resort.

What’s your favorite way to explore a destination?