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[Top] 91 15 Best Things to do in Old San Juan, Puerto Rico

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Old San Juan, Puerto Rico Walking Tour
Old San Juan, Puerto Rico Walking Tour

There are plenty of amazing things to do in Old San Juan. This guide looks at activities, places to eat and stay for those who are looking for an eco-conscious escape in one of the Caribbean’s most colorful and exciting towns.

It does get hot throughout the day, especially walking up and down the streets of Old San Juan. In general, the food and water standards of Puerto Rico are similar to mainland United States. Bring a reusable water bottle and fill up where you can, and for those who want a little extra precaution, try a Life Straw Bottle which has an inbuilt filter.

Here is our list of the best things to do in Old San Juan:

1. Wander the Colorful Streets

Old San Juan is filled with color. It’s easy to spend a day or two simply walking up and down the city grid.

Though it is hilly in some areas, it has sidewalks and the streets are generally pretty quiet, which makes it perfect for exploring on foot. Old San Juan is walkable in a day (if you move fast and don’t go up and down every street).

Whether you are interested in visiting the Catedral de San Juan Bautista, or the San Juan Gate, there is seemingly no end to the color and mystery.

It’s worth remembering that while the colorful streets of Old San Juan are a photographer’s dream, it is still a real place, and many of the colorful buildings are people’s homes. Be courteous when taking photos and avoid capturing people going about their daily lives (unless you specifically ask).

While most of the streets are colorful in their own right, there are a few particular streets that really stand out. Here are some to look out for:

Calle San Jose

This colorful street also has the iconic wall with the Puerto Rican Flag Door and people painted on the facade. Once in the traditional flag colors, the colors were changed in 2016 to emphasize the social and iconic struggle of the country.

Caleta De San Juan

This beautifully preserved street comes right off the Puerta de San Juan, which is the old gate that was the main entrance to the city during colonial times. Situated at the eastern end of town, this street has some amazing old trees in between the beautiful colored houses.

Fortaleza Street (The Umbrella Street)

One of the more famous streets in Old San Juan is Umbrella Street. Situated on Fortaleza street (Calle Fortaleza), towards La Fortaleza (the governor’s residence), is a colorful display of umbrellas in the sky. Installed after the hurricane, the Umbrella Sky Project is intended to bring color, fun, and joy into people’s lives.

Calle Sol

If you want to cross the city in the East/West direction, Calle Sol is a great one to do. It is relatively quiet (both in foot traffic and car traffic). Here the cobbled stone street is lined with all kinds of colorful buildings and churches. There are also some seriously old buildings under renovation that you can see inside.

Old San Juan walking tours

couple standing under the colourful sky umbrellas in old san juan puerto rico

With the guidance of David Rodriguez, author of ‘The Rise and Fall of the Great Barbate’ you can learn about the area’s main historic monuments and acquire fresh insights into Puerto Rican culture by exploring the streets of Old San Juan in this small group walking tour.

2. Snorkel with Turtles and Sealife

Looking for unique things to do in Old San Juan? Take a dive into the water! A variety of marine life may be seen in the waters near Old San Juan.

When snorkeling, you may often see sea turtles, octopuses, and tropical fish, among other things. If you don’t have your own snorkeling equipment or are a novice, it may be a good idea to join a snorkeling trip. Fortunately, there are a handful of options that are accessible in the area around Old San Juan.

Snorkeling in Puerto Rico is a great way to see the island’s underwater beauty. All of the necessary equipment is provided, and you can explore Guaynabo’s tropical seas. Spot sea turtles, tropical fish, and other marine life.

3. Explore Castillo San Cristobal and Castillo San Felipe del Morro

The town of Old San Juan is surrounded by walls and forts built by the Spanish during the colonial days.

While it is a stark reminder of the past, these forts do provide some breathtaking views of the town and coastlines. Inside the forts, there are information boards depicting life during colonial times. There are various tunnels and “dungeons” in which you can explore.

Exploring forts might not be one of the things to do in San Juan that you had in mind, but they really do have some amazing views!

Opening Hours: Open daily from 9:00am – 6:00pm

Entry Fee:

  • Children 15 and under: Free
  • Adults 16 and older: USD$5
  • Annual Passes: San Juan National Historic Site USD$25

There is a historical information video that shows every 15 minutes.

4. Join a Salsa Class

Have you ever wanted to learn how to salsa dance but didn’t know where to start? Puerto Rico is the ideal location to learn!

In San Juan, you can find a venue to dance any night of the week, regardless of whether you like salsa, reggaetón, house, plena, or bomba. Some establishments even offer free lessons on certain evenings of the week! Don’t forget to bring your dance shoes along with you.

5. Have a rooftop beer at sunset

When looking for a low-key, dive bar experience in Old San Juan, go no farther than La Vergüenza, a rooftop “chinchorro” with a welcoming and inviting ambiance. The bar has a beautiful view of the Atlantic Ocean and the San Cristóbal fort. The rooftop is the perfect spot to have a sunset cocktail. If you’re going to have a drink, be sure to bring your own reusable cup!

We were lucky enough to have an amazing rooftop overlooking the sea and old fort areas at our accommodation, La Capitana. The apartment was also managed by the owners of the La Terazza Hotel (only a few minutes walk down Calle Sol). As guests, we were allowed to use the facilities at the hotel, including the rooftop pool.

6. Go for a Sunset Sail

Take a relaxing sailing tour on the calm, blue seas of San Juan Bay, which happens to be one of the most beautiful things to do in Puerto Rico.

What better way to enjoy the sunset than on a catamaran or yacht? While sipping on some delectable beverages, take in a fresh view of Old San Juan. If you’re fortunate, you may be able to sight some dolphins while sailing!

During this cocktail cruise, you can enjoy the tranquil, turquoise waters of San Juan Bay around sunset. From the ocean, you can see Castillo San Felipe del Morro and Palacio de Santa Catalina up close.

7. Eat Delicious Food

Old San Juan is an amazing blend of cultures and food options. For those looking for a delicious meal, this city has got plenty to choose from! One of the best things to do in San Juan is to walk and eat. Then walk and eat some more!

Take a 3-hour eating and walking tour of Old San Juan’s cobblestone streets and sample some of the city’s specialties. Your guide will tell you everything about this colonial city’s rich history, and you’ll have time to stop at local coffee shops and cafés. Enjoy a rum cocktail and traditional Puerto Rican cuisine at four points.

Senor Paleta

Get a popsicle at Senor Paleta. This bustling popsicle shop gets busy from about midday onwards, and for a good reason. The cool, fresh fruit popsicles on wooden sticks are a great option for tropical walking days!

Vegetarian and Vegan Restaurants in Old San Juan

There are a couple of great options for vegetarians and vegans in Old San Juan. If you want something local, try the Mofongo (mashed plantain). The plantains (a kind of hearty banana) are picked green and fried, then mashed with salt, garlic, broth, and olive oil. This is often severed as a base with vegetables or some kind of sauce. You will need to ensure it’s vegan/vegetarian though, by asking whether it was cooked with any pork as this can often happen.

Vegan-Friendly Restaurants in Old San Juan

  • Cafe Berlin specialises in Puerto Rico cuisine and offers a vegan menu. Try the bbq guava loaf, vegan burger, spicy vegan tacos, or gluten-free pizza.
  • St Germain is a great little cafe that has some nice lunch options (salads, paninis, fresh bread, and hummus). Be sure to ask for no straw in your drink.
  • Verde Mesa is worth going to just for the eclectic interior. This intimate restaurant has some vegetarian and vegan options on its menu.

Ocean Park

  • Berlingeri has vegan burgers, stuffed avocado, plant-based bowls, and more.
  • Cocina Abierta has vegetarian meals on the menu with gluten-free and celiac options.
  • Cocobana has veggie burgers, juices and vegan alternatives to the traditional Puerto Rican meals (rice and bean-based)

Pack Reusables

There are some cafes that have converted to paper straws and cardboard takeaway containers. However, many of the street food vendors are using single use plastic.

It’s best to carry a small set of eco travel (reusable) items on your exploration. This is just one of the things to do in Old San Juan to make your trip a little bit greener!

>> Click here for reusable container options (alternatives to plastic bags)

8. Browse the Sustainable Shops

There are a few amazing shops in Old San Juan with sustainable fashion at their core. Be sure to check these places out if you’re in the market for holiday purchases.

  • Pure Soul and Pure Soul Living have a great collection of handmade homewares, linen clothing, local art, and handmade jewelry.
  • Concalama has some locally made housewares, jewelry, accessories, and some sustainable fashion brands.
  • Luca stocks local Puerto Rican designers and ethical slow fashion in the Ocean Park area.

9. Listen to a performance at the Gallery Inn Cannon Club

This really is a unique experience and should be on your list of things to do in Old San Juan! The Gallery Inn is a kind of kooky old building filled with labyrinth-style passages and fascinating pieces of art and sculptures everywhere.

But what makes it really special is its connection to the musical world. Specifically, pianos. The property has seven Steinway pianos scattered around in various rooms. The pianos are reserved for those who can actually play (for the longevity of the keys and the consideration of guests staying at the property).

You don’t have to be staying at the Gallery Inn to watch the live music in the funky downstairs bar, called the Cannon Club. This eclectic venue attracts a range of interesting characters to watch some of the most amazing pianists from around the world. If you’re looking for something different to do a night, check out this bar for a happy hour cocktail and a show!

The Cannon Club Old San Juan
The Gallery Inn Old San Juan

10. Visit Escambron beach

This palm tree-lined beach is a local favorite and is just a short walk from the historic district of Old San Juan (approximately a 25-minute walk from town along the ocean esplanade).

There are changing rooms, plenty of palm trees to get your tropical vibe fix, a sheltered swimming area, and even some waves for surfing.

If you need a respite from the hustle and bustle of the city streets, this is one among the things to do in Old San Juan that is well worth a sunset visit. Please keep in mind that sunset is one of the most peaceful times of the day since many of the beachgoers begin packing up and leaving the beach before the sun has even set.

11. Have a coffee at Caficultura

At Caficultura, you will find some of the finest coffee in the city. Located in the town square, it has a wide-open feel if you sit on one of the outside tables. This also makes for some great people watching to start your day.

The food is “farm to table,” and it is every bit as excellent as the coffee. This place has a fantastic ambiance, with enormous black chandeliers hanging from large wooden beams. It is also in close proximity to another highly colored street, Calle De O’Donnell.

12. Enjoy live music and outdoor dining along Paseo de la Princesa

This outdoor strip of dining options is right next to the cruise ship terminal area. However, it does have some good live music.

As a destination geared mainly toward cruise ship guests, it lacks some of the “grit” that you would find farther up the road (north of the city). However, there are some fantastic local tours available in the region that will take you to nightlife venues with live music that are off the main route, where you can also try local beer and street cuisine as well.

13. Party at La Factoria

This is a popular hangout in Old San Juan. The crumbling walls and dim lighting establish the tone, and the drinks that come over the bar are genuinely world-class in quality.
A fantastic mix of young, local artists, musicians, working professionals, and ex-pats can be found in the venue’s numerous rooms and bars. Make sure to have a mojito or two while you’re there.

14. Check out the beach ruins at Playa Peña Beach

Playa Pena Beach is located just beside the Castillo San Cristobal Fort. It is normally rather quiet, so you may be able to enjoy it all to yourself.

Old fort ruins that are crumbling into the ocean provide a pleasant spot to grab some shelter and cool down in the summer sun while enjoying a swim.

15. Get out of town and explore

Want to see more than Old San Juan? For those seeking new adventures, Puerto Rico provides a wide range of thrilling activities to choose from. Mineral holes, forests, and waterfalls can be found in abundance around the island, all of which are breathtakingly beautiful. Hiking, zip-lining, surfing, and other activities are offered for those who want to be active during their vacation.

Where to stay in Old San Juan:

With lots of accommodation types in Old San Juan (on various budgets), one of our recommendations is to rent a home.

There are some great apartments in Old San Juan, with beautiful terraces and patios. We love to rent homes when we travel, as they generally produce less waste and use less energy (and water) than hotels and resorts. It also provides the opportunity to cook your own meals, so you can cut costs.

Old San Juan Penthouse | VRBO

old san juan penthouse

This apartment welcomes you with a bright, open loft room with hardwood flooring. Relax in the living area, which has two fold-out futons and well-stocked wall unit bookshelves. The stunning patio, though, is the highlight of this penthouse. Sit back on the outside sectional couch and take in the breathtaking view of Old San Juan Bay.

Villa Blanca | VRBO

old san juan accommodation

This lovely Spanish-style villa features a high ceiling and arched windows. Attractions such as vibrant paintings and beautiful decor await you inside. Air conditioning and ceiling fans in the living and sleeping areas provide a comfortable night’s sleep.

Casa Sol

cafe sol

Casa Sol is a wonderful bed & breakfast that is able to accommodate vegetarians, vegans, and gluten-free diners! They are conscious of their environmental impact and have installed solar panels, collect rainwater, use energy-efficient equipment, and recycle waste materials.

The Dream Catcher | Hotel

Situated in Ocean Park, the Dream Catcher is a little way from the center of Old San Juan. However, it is a beautiful, boutique hotel that offers yoga, great vegetarian food, and close proximity to the beach. Each room is light and air-conditioned, and it is equipped with a Dreamcatcher. Suites also have a private bathroom as well as a balcony or patio.

The Gallery Inn

The Gallery Inn Old San Juan

There are amazing pieces of art and sculptures all around the Gallery Inn, which is a quirky old structure with labyrinth-style tunnels and fascinating pieces of art and sculptures everywhere.

This unique hotel in Old San Juan is known for its eccentric furnishings, piano rooms, and terrace pool, all making for an unforgettable visit.

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Traveling around the Caribbean?

There are some beautiful islands to visit in the Caribbean. Some of our favourites are:

  • Grenada: Luscious rainforests, beautiful beaches, jungle waterfalls
  • US Virgin Islands: Amazing snorkeling and picture-perfect beaches
  • British Virgin Islands
  • Carriacou
  • Jamaica: unique accommodation, hidden beaches, amazing waterfalls

Aaron Salyer writer

Aaron is one of the co-founders of The Dharma Trails. His background in marine eco tourism and writing have blended together to create the eco travel platform read by users around the world.

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