Exploring Old San Juan Before or After Your Caribbean Cruise

Welcome sign from cruise port

Puerto Rico, in particular San Juan, has so many different things to offer that when one only has a few days, it can be difficult to narrow it down! My grandmother and I decided to go on a Caribbean cruise that was set to depart from San Juan, and so we decided to go a few days ahead of time in order to experience this charming place as neither of us had been there before.

Of course, we had to stay near Old San Juan as it is one of the most well-known parts of Puerto Rico. We found that it was easily walkable to be able to get around that area of town. Make sure to wear good shoes though, as the blue cobblestones brought from England by the Spanish were used to pave some of the streets and tend to be uneven and a bit slippery, especially when it rains. The brightly colored buildings (done because they found it increased visitors and tourism to the island) help to highlight some of the beautiful architecture that can be found and vivid colors blend together to create postcard worthy moments.

Examples of some buildings' vibrancy

Things to do

If you have a short amount of time to visit this beautiful city, there are so many options to choose from, so it depends on what appeals to you the most! I recommend to try and make the most of it by exploring one of the beautiful beaches, taking a walking tour to learn more about the history of this melting pot of an island with its various cultures, checking out the Castillo San Felipe del Morro, sampling mofongo (mashed fried plantains with savory spices and stuffed with some kind of meat or seafood), drinking rum, or even going to a baseball game!

And for the coffee lovers out there, make sure to stop by Cuatros Sombras for a cup of single-origin Puerto Rican-grown coffee. This place is not just for tourists or visitors; I met many locals who recommended it and it is a neighborhood favorite.

Famous coffee shop in San Juan

Some fun little things you can find when you explore Old San Juan are if you can find one of the narrowest buildings in the world (La Casa Estrecha) or (one of the places) where the pina colada was claimed to first be created (Barrachina Restaurant or Caribe Hilton).

If you decided that you wanted to do a walking tour and find out more about the history of this town, I highly recommend Patria Tours. Our guide Melanie was fantastic and you could tell how passionate she was about sharing her knowledge of the history, the Puerto Rican people, and their highs and lows while giving you the facts, stops for photos, and answering any questions that anyone in the group may have had. I learned so much and it truly made me appreciate what I was looking at, where I was, and what happened to have Puerto Rico and in particular, San Juan, be the way that it is today. Be prepared for a lot of walking, but I believe it is one of the best ways to see someplace new.

Lookout point at Castillo San Felipe del Morro

Baseball

If walking around or history isn’t your thing, why not think outside the box and go to a baseball game? Puerto Rico alone has six baseball teams in its league (Liga de Béisbol Profesional Roberto Clemente (LBPRC) running from around November to around February. The stadium closest to those staying in Old San Juan is the Hiram Bithorn Stadium, which is set to host the World Baseball Classic in March 2026.

If you decide last minute that you wanted to go to a game like I did, you do not even have to buy a ticket ahead of time! You can take an Uber or taxi to the stadium and go to the box office to purchase a general admission ticket. It is very affordable and then you can sit wherever there's a seat available within the general admission area, which is a good portion of the stadium seating. It's a fun atmosphere with everyone getting into the game and you do not have to worry about going hungry or thirsty as there are plenty of concessions stands around!

Gorgeous florals

Dinner in the sky

Another option might be to see San Juan from a very different perspective, such as almost 150 feet up in the sky while enjoying drinks or dinner?! This unique concept (albeit I admit, may be a bit touristy) offers different times throughout the day of being suspended up in the air and enjoying happy hour with drinks or a four-course dining experience through Fly Dining Puerto Rico. The sunset dinner experience was fabulous, offering stunning views of Old San Juan, the harbor, and the sea. You’re safely strapped in and can spin around to capture the perfect shots of the city. The food was great, the servers were awesome, and the experience was certainly once in a lifetime.

Oh, and this was my grandma's idea, not mine! But we saw it from the balcony of our lovely hotel (Hotel Puerto Valdes) and we decided to just go for it!

View of harbor from Fly Dining

Accommodation

The hotel we stayed at was in a charming building that had some more recent renovations done, and it was perfect for our needs. The staff are warm, welcoming, and eager to help assist you in any way possible. They knew that we were going on a cruise and gave us late checkout so we didn't have to feel rushed when it was time to head to the cruise terminal.

Around the corner from this hotel was the perfect place for coffee, breakfast, or brunch, and it was giving us vibes of being back in Santa Monica or Venice Beach in California. Tostado Puerto de Tierra is where locals and tourists alike come to sit, enjoy a leisurely meal or coffee, and then meander back outside to walk along the beach or through one of the various neighborhoods.

Brunch at Tostado

In sum

When it was time to leave for our cruise, we both agreed that we had only touched upon a bit of what San Juan has to offer and that we cannot wait to come back! The warmth, the hospitality, the scenery, the food, and the location was incredible and there are more places on my list to come back to experience such as the El Yunque rainforest (where James Cameron was inspired to create Avatar), horseback riding on the beach, the Bacardi Rum distillery, and kayak one of the bioluminescent bays that this territory is famously known for.

The author in front of La Casa Estrecha

• Remember that you’re going to be in the tropics, so make sure to pack an umbrella! Even rain showers of 10 minutes would come pouring down and soak you if you weren’t prepared, so have that added to your packing list.

• Make sure to keep your phone or camera out. You never know what picture-worthy shot is around the next corner!

• The one final caveat I will say is to keep in mind when the holidays are. They celebrate both US holidays and their own, and when that happens, the majority of places (restaurants, bars, shops, etc) will be closed! So either be prepared or be flexible with adjusting your dates as needed if you want to avoid this!

For more inspiration and insider recommendations, visit our San Juan page.