The 15 BEST Things to do in Old San Juan, Puerto Rico

Old San Juan has a rich history with colourful architecture, and vibrant streets (like the iconic umbrella street and Calle San Jose). There are plenty of amazing things to do in Old San Juan, we spent a week in this beautiful town and explored rooftop bars, nearby beaches, sustainable fashion stores and Puerto Rico landmarks. If you’re visiting soon and looking for the best things to do in Old San Juan, you’ve come to the right place. We’ve listed activities, places to eat and where to stay for those who are looking for an eco-conscious escape in one of the Caribbean’s most colourful and exciting towns.

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

1. Explore the Colorful Streets of Old San Juan

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. Joining a guided walking tour is one of the best things to do in Old San Juan, and is an excellent way to learn about the history and culture of this colorful town from someone local.

From iconic landmarks in Puerto Rico like the Catedral de San Juan Bautista to the historic San Juan Gate, every corner is filled with color and mystery. But always remember, behind the colorful facades are real 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 and you definitely should add to your list of things to do in Old San Juan:

• 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 Old San Juan Umbrella Street): One of the best things to do in Old San Juan, is visiting this iconic street. This street hosts a vibrant array of umbrellas suspended in mid-air. Situated on Fortaleza street (Calle Fortaleza) near La Fortaleza (the governor’s residence), the Umbrella Sky Project emerged post-hurricane as a beacon of hope, symbolizing resilience and joy.
• 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 restoration, revealing glimpses of their interiors.

2. Go for a Sunset Sail

Experience sunset sailing in Puerto Rico, on the calm, blue seas of San Juan Bay, is one of the most scenic things to do in Old San Juan.

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!

3. Snorkel with Turtles and Sea life

Looking for unique things to do in Old San Juan? Take a dive into the water! The waters surrounding Old San Juan have an abundance of marine life.

When snorkeling, you can often spot sea turtles, octopuses, and an array of tropical fish. If you’re not equipped with snorkeling gear or are new to the experience, consider joining a guided snorkeling trip. A number of tours operate in and around Old San Juan, making it convenient for travelers.

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 by joining a salsa class!

In Old 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 lessons on certain evenings of the week! Don’t forget to bring your dancing shoes along with you.

5. Have a rooftop beer at sunset

What better way to spend the afternoon and sunset, then at a rooftop bar in Old San Juan, overlooking the colourful streets below. Some of our favourites include:

• The Mezzanine – great cocktails and fish tacos
• Al Fresco – a wine bar with a view
• La Terazza – rooftop pool bar with views of the bay and city
• Atelier Rooftop Terrace – a modern luxe vibe with artisan cocktails
• Bar Catedral – a nice casual feel with views of the Catedral de San Juan Bautista
• La Vergüenza PR Chinchorro – a busy bar with views of the Atlantic Ocean

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, and hanging out there at sunset was one of our favourite things to do in Old San Juan.

6. 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 and there is a historical information video that shows every 15 minutes. You can navigate through the intricate tunnels and venture into the “dungeons” for an immersive experience.

Exploring forts might not be one of the things to do in Old San Juan that you had in mind, but they really do have some amazing views! You can explore the forts independently, or join a guided tour for an in depth experience.

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

7. Savor the Culinary Delights of Old San Juan

One of the best things to do in Old San Juan if you are a food lover, is going on one of the walking food tours! Old San Juan is a melting pot of diverse cultures and boasts a culinary scene as vibrant as its streets. From the fragrant aroma of traditional Puerto Rican dishes to the innovative fusion of international flavors, the city invites you to go on a gastronomic journey.

Start your morning with a delicious cup of locally roasted coffee at Café Don Ruiz or Caficultura. Then, venture into the streets and try the local dish “mofongo” – made of mashed plantains, broth and garlic, and pork (some places offer a vegetarian version too). For an afternoon sweet treat, stop by 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!

8. Discover Sustainable Shopping in Old San Juan

Another one of our favourite things to do in Old San Juan was checking out the sustainable shops in town. If you’re looking for eco and ethically sourced holiday gifts or sustainable fashion, several shops in the town prioritize sustainability and local craftsmanship:

• Pure Soul and Pure Soul Living: These twin boutiques are a must-visit. Offering a curated selection of handmade homewares, linen clothing, local art, and artisanal jewelry, they epitomize sustainability with style.
• Concalama: This gem of a shop celebrates local artisans by showcasing housewares crafted in Puerto Rico, bespoke jewelry, handpicked accessories, and a line-up of sustainable fashion brands that meld style with ethics.
• Luca: Located in the scenic Ocean Park area, Luca is the destination for fashion lovers. The store proudly features local Puerto Rican designers and champions the slow fashion movement, presenting a collection that’s both ethical and trendy.

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

This really is a unique experience and was one of our favourite 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!

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 best things to do in Puerto Rico 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. Experience Authentic Puerto Rican Rum in Old San Juan

Puerto Rico’s intimate relationship with rum is as rich and profound as the flavors swirling in your glass. As you step onto the historic cobblestones of Old San Juan, you’re walking on centuries-old stories of rum crafters and connoisseurs. With the country crafting over 80 distinctive types of rum, each visit to a local rum shop is an adventure.

One of the best Old San Juan attractions is enjoying the cocktails at the incredible bars. An easy way to do this is by joining a tasting tour, or you can even partake in a mixology class! Some of our favourite bars in Old San Juan are:

• The Cannon Club
• La Factoria
• Deshistoria
• El Batey
• Anitguo 26
• La Taberna Lupolo
• El Adoquin Del Patio
• La Cubanita
• The Mezzanine
• La Terraza
• Bar Catedral

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

Heading to Paseo de la Princesa for dinner is one of the most popular things to do in Old San Juan for cruise shippers. This outdoor strip of dining options is right next to the cruise ship terminal area and has some great 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 great hangout and one of the most popular things to do 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 cocktail or two while you’re there. If you’re looking to experience Old San Juan’s nightlife and don’t know where to start, you can join a local bar crawl experience.

14. Check out the beach ruins at Playa Peña Beach

Tucked away adjacent to the Castillo San Cristobal Fort, Playa Peña Beach is a hidden gem that often remains undiscovered by the usual throng of tourists. Its quiet ambiance offers a serene respite, making it likely that you’ll have this secluded paradise to yourself.

A striking feature of this beach is the ancient fort ruins, slowly being reclaimed by the sea. These timeworn remnants of history serve as both a testament to the island’s storied past and a shady refuge for visitors. Imagine taking a refreshing dip in the crystal-clear waters, then resting beneath the protective arches of these ruins, feeling the cool breeze as you soak up the surrounding beauty – it was one of the most unique things to do in Old San Juan.

15. Have a drink at Old San Juan’s oldest bar

There are some amazing bars in Old San Juan to visit on your trip! Frequented by the likes of Hunter S. Thompson and the Rolling Stones in the 1960s, El Batey has become an icon in Old San Juan as the oldest, and one of the coolest dive bars. There’s graffiti and murals all over the walls, business cards hanging from lights, a pool table, and generous bar tenders. If you like checking out local bars, you definitely need to add this to your list of things to do in Old San Juan!

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

Villa Blanca | VRBO

Casa Sol

The Dream Catcher | Hotel

The Gallery Inn

FAQ

How do you spend a day in Old San Juan, Puerto Rico?

Begin with a locally roasted coffee at Café Don Ruiz, then take a walk to visit the historic forts, Castillo San Cristobal and Castillo San Felipe del Morro, for panoramic views of the city and coastline. Stroll through the vibrant, colorful streets, soaking in the culture and consider joining a walking tour to dive deeper into its history. Take a lunch break at one of the local eateries, sampling traditional Puerto Rican cuisine like Mofongo. In the afternoon, you can indulge in some shopping, exploring sustainable shops and local boutiques. As the sun sets, enjoy the nightlife with local rum-infused cocktails, and join a salsa class to dance the night away.

How long should you spend in Old San Juan?

While you can get a taste of Old San Juan in a day, spending three days allows you to immerse yourself deeper in its history, culture, and vibrant atmosphere. This gives you ample time to explore the landmarks, indulge in local cuisine, shop, and even relax on nearby beaches.

What is so special about Old San Juan?

Old San Juan, a UNESCO World Heritage Site, is a beautiful blend of Spanish colonial architecture, rich history, and vibrant Puerto Rican culture. Its cobblestone streets are lined with colorful buildings, historic sites, and bustling plazas. The city is also home to ancient forts, providing glimpses into its storied past, while its local shops and eateries offer a contemporary taste of Puerto Rican life.

Does Old San Juan have nightlife?

Absolutely! Old San Juan comes alive in the evenings. There are several bars, pubs, and lounges where you can enjoy local music, dance, and especially the island’s famed rum. Whether you’re looking to sip on handcrafted cocktails, dance to salsa beats, or simply soak in the nighttime ambiance of this historic town, Old San Juan has something for every nocturnal adventurer.

Can you walk to the beach from Old San Juan?

Yes, you can. While Old San Juan itself is more known for its history and architecture, there are nearby beaches accessible by a short walk or drive. We walked to Escambron beach, which is approximately a 25-minute walk from town along the ocean esplanade. This palm tree-lined beach is a local favorite and a great spot to watch the sunset.

Where is the Old San Juan Umbrella Street?

The Old San Juan Umbrella Street, commonly known as “Umbrella Sky Project,” is located on Fortaleza Street (Calle Fortaleza) and visiting it is one of the most popular instragrammable things to do in Old San Juan, Puerto Rico. This vibrant display features a canopy of colorful umbrellas suspended overhead, creating a picturesque and shaded pathway. It’s become a popular spot for both locals and tourists, offering a delightful backdrop for photos and a unique urban experience amidst the historic charm of the town.

Eco Travel Tips

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)

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.

Vegan-Friendly Restaurants in 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)

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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