Puerto Rico 2026

We recently flew down to Puerto Rico to spend 10 days exploring the Isle of Enchantment with our very good friends from Spain, Yvonne and Nigel. Yolie had planned out a great itinerary where we would circle the island. During our visit we: 1) Celebrated in the streets of Old San Juan; 2) Reconnected with friends; 3) Made new friends; 4) Spent some quality family time; 5) Had new experiences, and; 6) Drank with some super bartenders.

1. The San Sebastián Street Festival held in Old San Juan the third weekend in January was our first stop. This year’s festival, which ran 15-18 January, drew over 1.1 million visitors to the narrow streets of Old San Juan. We had a blast dancing to the beat of Puerto Rican music; slaking our thirsts with the local Medalla Beer, and; grazing on a variety of local cuisine…Yolie’s favorite being octopus salad! Meanwhile, me and our friends leaned towards the pinchos, both pork and chicken, slathered with barbecue sauce.

   

   

   

   

   

   

   

   

2. While in Old San Juan we had the great pleasure of reconnecting with friends, Brian and Tito. Besides bar hopping in Old San Juan, we also met up with then for a rousing Friday night in Santurce. Santurce had great music, good food, and cheap drinks. That bears repeating…really cheap drinks! The cold Medallas were flowing and the rum and cokes were plentiful. Remember, when in Puerto Rico, it is Don Q rum and NOT Bacardi for your Cuba Libre. Oddly, Bacardi is the largest rum distillery in the world and just spitting distance from San Juan, but Puerto Ricans won’t drink it as they still view it as “Cuban Rum”. In addition to Brian and Tito, we also caught up with Dave while in San Juan. We had a great time hanging with Dave, but one poor local had too great of a time. Apparently, she passed out in a locked bathroom, and had to be sprung from the loo and ultimately taken out on a stretcher with an IV bag attached. We’ve been to a lot of bars, but an EMT assisted exit was a first for us. We also caught up with a couple of friends, Gleniarys and Raul, in Ponce (my favorite town in Puerto Rico). We saw one of our favorite bartenders, Gleniarys at Papa Rupe Brewing Company. Also while in Ponce, we received a master class from expert animal trainer, Raul. We learned a lot from him making our trip truly funducational.

3. Besides carousing with our old friends, we also made some new friends. Nigel, a staunch Arsenal Football Club supporter (that’s a soccer team in England’s Premier League), REALLY wanted to see Arsenal’s match with Chelsea. Wouldn’t you know we came across the only Chelsea supporter in Old San Juan who was equally interested in seeing the game. We watched the first half in a bar on “Chelsea Guy’s” cell phone. While watching we received a gracious offer from Alan, our new friend, to see the second half on her television around the corner. Nigel and I quickly took her up on the generous offer. We had a great time cheering the Gunners on to victory. Meanwhile, Chelsea Guy, who was watching the game down the block, would periodically appear at Alan’s window after a Chelsea goal. Arsenal ultimately prevailed and we all celebrated heartily. While partying at La Sombrilla Rosa (The Pink Umbrella), which was directly across the street from Alan’s place, we met John. He was off one of the cruise ships docked nearby and he spends his time just going from one cruise to another. Basically, he’s living on cruise ships. A very interesting life, indeed!

4. Yolie still has family in Puerto Rico so naturally we spent a couple days in her old hometown of San German and visiting the family’s farm. San German is Puerto Rico’s second oldest city and its historic downtown is the site of the Porta Coeli church, one of the earliest Spanish churches built in the Americas. We had fun spending the evenings visiting San Germans watering holes, like the Sonic, Roosters, and Lupito’s. While during the days we spent precious quality time with family, eating homemade delicacies, and feeding the flock.

5. While circling the island we saw many of our favorite places: Old San Juan; Pinones; El Yunque National Forest; Luquillo Beach, Ponce; San German; La Parguera; and Rincón. However, we also had the opportunity to experience a number of new places. One new place was La Ruta del Lechon, also known as the Pork Highway. As the name suggests, the road is chock full of restaurants featuring pork! Pigs on spits are a common sight all along the way. We also visited the lovely waterfront town of Cabo Rojo, where we were treated to a lovely sunset along with our equally lovely cocktails. Last but not least, we got to experience Santurce on a Friday night. Santurce is ground zero for music, dancing, and partying in Puerto Rico. Even though Yolie has lived in Puerto Rico and has visited there many times, the island still held new and wonderful things to see and do.

6. If you’re a regular reader of our blog you know we enjoy nothing better than cool bars with great bartenders. There are lots of those in Puerto Rico, but two stood out for us. La Sombrilla Rosa in Old San Juan was our go to place before, during, and after the San Sebastián Street Festival. The fun atmosphere there was a blast, and the lovely Paloma behind the bar was a godsend. The festival brought in throngs of people, but her fetching smile, sparkling personality, and lightening fast delivery of Medallas and Gasolinas, kept everything and everyone under control. The second spot that stood out was Calle 13 in Luquillo Beach. The laid back bar was a perfect fit for the gorgeous beach scenery. Manning the bar was, Edgar. This was our last bar at Luquillo Beach and we only stopped in for a quick one for the road. However, Edgar’s cool entertaining style made us linger much longer. There are plenty of places to eat and drink at Luquillo beach, but you must go to Calle 13 and have a couple rounds with Edgar. You won’t be disappointed!

Well, that was just some of the highlights from our ten day tour of Puerto Rico with Yvonne and Nigel. We look forward to going back to the Isle of Enchantment to visit old friends and familiar places, and to make new friends and have unexpected adventures. Once again we praise God for safe travels!