San Juan, Puerto Rico: History, Rum, and a Reason to Return
“Too much of anything is bad, but too much good rum is barely enough.” Mark Twain
4/6/20267 min read
We have been to San Juan, Puerto Rico twice, and we love it. It is one of those destinations that immediately pulls you in with its energy, history, and character, and then keeps you coming back for more.
San Juan is one of the oldest cities in the Americas, founded by the Spanish in 1521. Its strategic location made it a key military and shipping hub for Spain, which is why so much of its historic architecture is centered around defense. Today, Old San Juan is a UNESCO World Heritage Site, known for its colorful colonial buildings, blue cobblestone streets, and massive forts that overlook the Atlantic Ocean. Since Puerto Rico is a United States territory, there is no passport required for US travelers, and the US dollar is used, which makes visiting easy.
On our first trip, as we mentioned in our article Ports of Call on a Seven Day Celebrity Eclipse Cruise (Antigua, St Maarten, San Juan, Puerto Plata), we primarily focused on the old town, the history, and of course the food.
We started with a walking tour that included Castillo San Cristóbal and the nearby Cementerio Santa María Magdalena de Pazzis. The views along the coast are striking, and the sense of history is tangible as you walk through the grounds and along the old stone walls.
We also visited Castillo San Felipe del Morro, often referred to simply as El Morro. The lighthouse, Faro del Castillo San Felipe del Morro, is another worthwhile stop and helps round out the experience. If you have a Parks Pass that allows entry into US National Parks, be sure to bring it. Since these sites are part of the National Park system, you can enter for free with the pass. Each pass allows up to four guests, so if you do not have one, it is worth asking around. Admission is otherwise ten dollars per person and covers both forts.
On that first trip, we also visited and immediately fell in love with the restaurant Barrachina, which is known as the birthplace of the piña colada. Jorge, one of the bartenders, has been working there for over twenty five years and is someone you will want to talk to if you get the chance. A small piña colada costs $10, with larger versions just under $13.
Beyond the drinks, the food impressed us. The pork chop was outstanding, and the lobster tail was generously sized. Afterward, for a quick and very local experience, we stopped at Chichaitos, located on Calle del Cristo next door to Starbucks. They offer one dollar shots and a fun, laid back atmosphere. Jorge from Barrachina pointed us in that direction, and it ended up being a great recommendation.
On our second visit, we took a completely different approach. Instead of following a plan, we wandered the streets of Old San Juan with no real agenda. We explored local shops, admired the architecture, and just enjoyed the atmosphere of the city.
Eventually, we built up an appetite and, more importantly, a thirst, and made our way back to see our friend Jorge at Barrachina. With a little luck, we were able to grab seats at the bar, which we believe is the best way to experience the restaurant. Sitting there gives you the chance to interact with Jorge and the team and really enjoy the moment.
We ordered a few more piña coladas and the Can Can pork chop, which somehow only costs $24. It is massive. We split it and still could not finish it.
There is something about Puerto Rico that keeps pulling us back. It could be the rum in Jorge’s drinks, the history that surrounds you, or just the constant ocean breeze, but it is a place that feels easy, welcoming, and worth returning to.
San Juan is a destination that offers a perfect mix of history, culture, and great food, all within walking distance of the cruise port.
If you only have one day, focus on Old San Juan, explore the forts, and make time for a long lunch at Barrachina. If you have more time, this is absolutely a place worth coming back to and staying for a week.
We know we will.
We have been to San Juan, Puerto Rico twice, and we love it. It is one of those destinations that immediately pulls you in with its energy, history, and character, and then keeps you coming back for more.
San Juan is one of the oldest cities in the Americas, founded by the Spanish in 1521. Its strategic location made it a key military and shipping hub for Spain, which is why so much of its historic architecture is centered around defense. Today, Old San Juan is a UNESCO World Heritage Site, known for its colorful colonial buildings, blue cobblestone streets, and massive forts that overlook the Atlantic Ocean. Since Puerto Rico is a United States territory, there is no passport required for US travelers, and the US dollar is used, which makes visiting easy.
On our first trip, as we mentioned in our article Ports of Call on a Seven Day Celebrity Eclipse Cruise (Antigua, St Maarten, San Juan, Puerto Plata), we primarily focused on the old town, the history, and of course the food.
We started with a walking tour that included Castillo San Cristóbal and the nearby Cementerio Santa María Magdalena de Pazzis. The views along the coast are striking, and the sense of history is tangible as you walk through the grounds and along the old stone walls.
We also visited Castillo San Felipe del Morro, often referred to simply as El Morro. The lighthouse, Faro del Castillo San Felipe del Morro, is another worthwhile stop and helps round out the experience. If you have a Parks Pass that allows entry into US National Parks, be sure to bring it. Since these sites are part of the National Park system, you can enter for free with the pass. Each pass allows up to four guests, so if you do not have one, it is worth asking around. Admission is otherwise ten dollars per person and covers both forts.
On that first trip, we also visited and immediately fell in love with the restaurant Barrachina, which is known as the birthplace of the piña colada. Jorge, one of the bartenders, has been working there for over twenty five years and is someone you will want to talk to if you get the chance. A small piña colada costs $10, with larger versions just under $13.
Beyond the drinks, the food impressed us. The pork chop was outstanding, and the lobster tail was generously sized. Afterward, for a quick and very local experience, we stopped at Chichaitos, located on Calle del Cristo next door to Starbucks. They offer one dollar shots and a fun, laid back atmosphere. Jorge from Barrachina pointed us in that direction, and it ended up being a great recommendation.
On our second visit, we took a completely different approach. Instead of following a plan, we wandered the streets of Old San Juan with no real agenda. We explored local shops, admired the architecture, and just enjoyed the atmosphere of the city.
Eventually, we built up an appetite and, more importantly, a thirst, and made our way back to see our friend Jorge at Barrachina. With a little luck, we were able to grab seats at the bar, which we believe is the best way to experience the restaurant. Sitting there gives you the chance to interact with Jorge and the team and really enjoy the moment.
We ordered a few more piña coladas and the Can Can pork chop, which somehow only costs $24. It is massive. We split it and still could not finish it.
There is something about Puerto Rico that keeps pulling us back. It could be the rum in Jorge’s drinks, the history that surrounds you, or just the constant ocean breeze, but it is a place that feels easy, welcoming, and worth returning to.
San Juan is a destination that offers a perfect mix of history, culture, and great food, all within walking distance of the cruise port.
If you only have one day, focus on Old San Juan, explore the forts, and make time for a long lunch at Barrachina. If you have more time, this is absolutely a place worth coming back to and staying for a week.
We know we will.
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