Exploring Old San Juan, Puerto Rico

Whether you’re heading over for just a long weekend or a few weeks you’ll want to include exploring Old San Juan on your itinerary. Just a two and a half hour flight from Orlando you’ll step into another world, without even having the leave the country. Puerto Rico is a beautiful getaway filled with culture, history, delicious food, beautiful beaches, rainforest, and so much more.

Just a two and a half hour flight from Orlando you’ll step into another world, without even having the leave the country. Puerto Rico is a beautiful getaway filled with culture, history, delicious food, beautiful beaches, rainforest, and so much more.

Visiting Old San Juan allows you to wander the historic cobblestone streets of the colonial days while enjoying a lively city today.Top things to do when exploring Old San Juan. Where to stay, what to eat, exploring the nightlife, history, and more.

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Stay in the city center

While there are great places to stay along the beaches of San Juan and in the bigger city, there is nothing like saying right in Old San Juan. Leave the car and take a taxi in from the airport. You’ll be able to walk to everything you need as you’re exploring Old San Juan.

If you’re looking for a little luxury check out the Sheraton Old San Juan that has a beautiful view right on the harbor and is easy to explore from. Or stay a night in Hotel El Convento, which combines the historical feel of Old San Juan and luxury of a four-star hotel.

If you’re sticking to a budget you’ll want to reserve a room at Posada San Francisco. If you’re up for a dorm room you can stay for as little as $13 a night. Private rooms, where I stayed, are a perfect budget option costing only $50 a night. I like to describe Posada San Francisco as a hostel for adults, simple accommodations but a quiet and relaxing spot in the best part of town.

Enjoy local & international cuisines

Like so many major cities you’ll find twists on local favorites and international cuisines. While I stuck to Puerto Rican food as I explored the rest of the island in Old San Juan I took advantage of the variety of cuisine that they had perfect in the city.

Start your morning with a great little coffee shop, Caficultura, filled with locals and tourists just next to our Posado (guest house). I stopped in both mornings I stayed in Old San Juan, once for a grab and go coffee and the next day we sat down and enjoyed their eggs, Benedict. Order a cortadito and a quesito for a quick start to the morning, two of favorites as well. The cortadito, an espresso with a dollop of steamed milk and the quesito, a puff pastry with a sweet glaze filled with cream cheese.

One part of exploring Old San Juan is exploring the food. Consider starting with cocktails and appetizers in one spot, then head off to dinners in another. A perfect spot to start is the Mezzanine at the St. Germain. The cocktails had a nice twist and happy hour ran until 8. The environment was a low-key lounge but with décor that fit perfectly with the Old San Juan building. Ornate chairs and mirrors and the walls of the building showing their age. The whole place was a perfect balance of the old and the new.Top things to do when exploring Old San Juan. Where to stay, what to eat, exploring the nightlife, history, and more.

For dinner consider Pirilo, which had a great feel of a homey New York pizza shop with some island flair. Start with some of the best empanadas and a nice bottle of tempranillo. And follow it with one of their delicious pizzas, with choices ranging from a traditional margarita to Puerto Rican flavors.

Take in the history of Old San Juan

Wander in the general direction of Castillo San Felipe del Morro (El Morro), the 16th Century fortress on the bay, in the mean time you’ll wander by a variety of shops and enjoyed the beauty of the brightly painted buildings and the almost glowing blue stone streets if you happen to catch it in the rain.Top things to do when exploring Old San Juan. Where to stay, what to eat, exploring the nightlife, history, and more.

To escape the rain or the heat you’ll want to pop into one of the museums like the Mueso del Americas. The museum focused on both Puerto Rico and the greater Americas including the native tribes, colonial history and the impact of the slave trades. The permanent exhibits were very similar to ones you’d find in California but the temporary exhibits were three different Puerto Rican artists and breathtaking.

These included the modern art of Luis Maisonet Ramos and David Rodriguez, the traditional altarpieces of Edwin Baez Carrasquillo, and a Puerto Rican twist to Venetian masks by Hiram Montalvo. These exhibits were well worth the $3 ticket and staying dry for a little while.

Then make your way up the hill to El Morro. I don’t think this is a memory I will ever forget, exploring a 16th-century fort on the edge of the Caribbean while running around trying not to get soaked int he rain. The fort was beautiful, grand, epic and full of stories, plus it had magnificent views.

Find some shopping & sightseeing

If you’re looking to rest your feet, hop on the free trolley that runs throughout Old San Juan. It provides a good feel for the city including driving by the Capitol building, both of the forts and enjoying more stunning streets and building.

Hop off near Calle Cristo and walk along past the outlet stores and window shopped. As you move back toward Calle San Francisco you’ll find local shops full of crafts and art. If you’re looking to bring home more than just trinkets I recommend doing your shopping in Old San Juan.

Experience the night life

After dinner wander along Calle San Sebastian, which is lined with a range of nightlife. From local eateries with the game on to “discotecas”. There are so many places to explore but you’ll want to at least pop into La Factoria. A world famous club that truly had a spot for everyone with four distinct rooms.

First you had a bar/pub styled room, the next was more of a cocktail/wine lounge, then a quiet wine room and finally a nightclub. We plopped down in the cocktail room and enjoyed a drink. The place was busy with a good vibe without getting too loud or packed.Top things to do when exploring Old San Juan. Where to stay, what to eat, exploring the nightlife, history, and more.

Head to the beach

If you’re exploring more of Puerto Rico, odds are you’ll be heading to a beach during your trip. But if not, another great thing about Old San Juan is how close it is to the San Juan Beaches of Ocean Park and  Isla Verde. You can relax at a resort or a great boutique hotel even just for the day.Top things to do when exploring Old San Juan. Where to stay, what to eat, exploring the nightlife, history, and more.

Get the Most of Exploring Old San Juan

Old San Juan finds a beautiful balance of history and liveliness. It’s a city that offers enough to explore for more than just a few days. If you pop down for just a weekend you’ll get a taste of it, or if you stay longer it can make a great launchpad for exploring more of what Puerto Rico has to offer.

Heading to Puerto Rico anytime soon? Don’t forget to check out my To Do List for the island.

For more information about exploring Old San Juan and Puerto Rico check out these great books on Amazon including Fodor Travel’s Puerto Rico, Lonely Planet’s Puerto Rico, and Frommer’s Easy Guide to Puerto Rico.


Traveling to Puerto Rico Soon?

You’ll need a place or two to stay as you spend your time exploring Old San Juan, Puerto Rico.
Learn more about and book more fantastic hotels in Puerto Rico on Priceline and TripAdvisor.


Top things to do when exploring Old San Juan. Where to stay, what to eat, exploring the nightlife, history, and more.Top things to do when exploring Old San Juan. Where to stay, what to eat, exploring the nightlife, history, and more.

About Megan

Megan MacNee is the founder of Traveling Nine to Fiver. From nine to five she works in the political world in California, but on evening and weekends spends time exploring the West Coast and more. All while encouraging others to join in on the adventures.