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Are you looking for a unique and exciting vacation destination? Look no further than Old San Juan, Puerto Rico!
From its stunning colonial architecture to its vibrant culture and lively nightlife, this Caribbean city is sure to provide you with an unforgettable experience.
San Juan is one of my all-time favorite cities and is sure to be one of your favorite stops if you are on a Southern Caribbean Cruise.
🇵🇷Wondering what to do in Old San Juan Puerto Rico?
With over 40 fun activities to choose from, there’s something for everyone in Old San Juan – whether you’re the type that loves exploring nature or prefers relaxing in luxury.
If you have a few days in Puerto Rico or just a few hours as a cruise stop, you can see and do so much right from Old San Juan!
if you’re ready for your next adventure, read on to learn more about what awaits you in Old San Juan!
Best Things to do in Old San Juan Puerto Rico on a Cruise
If your cruise begins or ends in San Juan, I suggest staying a few extra days before or after to really get immersed in the culture and history of San Juan.
But, if you only have one day, no worries, you can still see a lot, and it will make you want to come back for more!
1. Visit La Fortaleza
La Fortaleza, or Palacio de Santa Catalina, is one of the most iconic sites in Old San Juan. It is the oldest executive mansion in continuous use in the New World and is the official residence of the Governor of Puerto Rico.
La Fortaleza was built between 1533 and 1540 to defend the harbor of San Juan.
The fortress gives visitors a glimpse into Puerto Rican history and is now part of the San Juan National Historic Site and is a UNESCO World Heritage site.
Tours are available on the weekdays, and you will be asked for a monetary donation.
2. Take Photos with the Umbrellas on Fortaleza Street
Ahhh, this is the stuff Instagram dreams are made of! The brightly colored umbrellas overhead as you walk through the street will make you want to take hundreds of photos.
The umbrellas were initially hung after a big storm to bring color and hope to the city.
From time to time, the umbrellas are taken down. Sometimes they are replaced with white, sometimes with a large Puerto Rican Flag, and sometimes there are strings of lights.
I have not visited San Juan in 2023, so I’m not sure what it currently looks like, but since it leads to La Fortaleza, it is not out of the way to swing by and check it out.
Be sure to also check out the art galleries and shops in this area, known for its hip design stores and galleries.
3. Castillo San Cristóbal
Castillo San Cristóbal is a stunning and vast 18th-century fortification built by the Spanish to protect the city of San Juan from land-based attacks.
Named after the saint patron of land travelers, Saint Christopher, Castillo San Cristóbal. It is the largest fortification in the Americas, covering over 27 acres of land, and holds immense historical significance for Puerto Rico in particular, and for the Caribbean region as a whole.
Castillo San Cristóbal consists of 3 levels and took 150 years to build.
At the entrance to the fortification is a small building known as Garita del Diablo, or “Devil’s Sentry Box.”
One of the most remarkable characteristics of San Cristóbal is its dungeon, where you can find ancient drawings from an unidentified inmate that date back to the late 18th century.
It was in this very place where a monk had been shackled to a wall for more than two decades due to his murder conviction.
During World War II, the US Army added two coastal observation posts and a 1942 bunker, which now serves as our Visitors’ Center.
At the visitors center, you can watch an informative movie about this park’s history in both English and Spanish at the theater inside.
San Cristóbal is part of the San Juan National Historic Site, and entrance fees apply. The fee is the same as El Morro, and one fee gives you access to both sites within 24 hours.
The views from up top are great! You can even see El Morro in the distance!
4. Castillo San Felipe del Morro
Castillo San Felipe del Morro, also known as El Morro, is a powerful 16th-century citadel located in Old San Juan, Puerto Rico.
This fortress was constructed to protect the city from attacks made by sea, and it still stands today with its original cannons facing the ocean. The impressive construction of this fortification consists of six staggered levels with barracks, dungeons, and storerooms.
You can explore the grounds of El Morro or take part in a guided tour to learn more about its fascinating history.
El Morro is run by the US National Park Service. The fee for entry is $10 for each adult for a 24-hour pass. Children under 15 are free. This pass gives you access to El Morro and Castillo San Cristóbal.
If you have the America The Beautiful Pass, the Lifetime Senior Pass, the active US Military Pass, Access Pass, or have a 4th grader, your entrance will be free.
You can spend hours wandering around here, I don’t think we ever did see it all! The grounds that surround it are beautiful and a great place to have a picnic lunch!
5. Try a Piña Colada
Did you know the Piña Colada was first made in Puerto Rico? This means it’s practically sinful to visit San Juan without trying one!
The piña colada is the official drink of Puerto Rico and is enjoyed by many all around the world. It was first made in 1963 by Don Ramon Portas Mingot, at his bar in old San Juan, La Barrachina.
The ingredients for this refreshing, creamy cocktail include white rum, pineapple juice, coconut cream, and crushed ice.
The piña colada is also said to have medicinal properties, which can help with digestion and give a boost of energy. (see, it’s healthy.)
So, if you are in need of some extra energy for your sightseeing adventures around the city, why not give it a try?
There’s no shortage of bars and restaurants serving up the delicious piña colada in San Juan, so don’t miss out on this iconic Puerto Rican experience!
6. Cobblestone Streets
Wandering aimlessly through the cobblestone streets of Old San Juan is completely free and fascinating enough to keep you busy for hours.
The old city is known for its brightly colored buildings, wrought-iron balconies, and ancient fortifications.
It’s also possible to get lost in picturesque streets full of lively restaurants, cafes, shops, and galleries. As you meander through the narrow lanes, you’ll come across small plazas overflowing with life.
The streets of Old San Juan tell the story of centuries of depth and history, making it a perfect place to simply explore and enjoy the city’s culture.
So grab your camera, comfortable shoes, and plenty of sunscreen, and get ready to wander! Oh! And bring water, its hot and humid out there!
7. Walking tour
Taking a walking tour in San Juan is a great way to explore the city. You can get up close and personal with the sights and sounds of the city, learn about its history, and meet new people.
As mentioned above, walking through the city is a wonderful experience, and having the opportunity to explore the city with a local can give you insights that you would not be able to get by touring San Juan on your own.
8. Walk through San Juan Gate
The San Juan Gate, also known as Puerta de Aguas or Puerta de San Juan, is a centuries-old entrance to Old San Juan that stands 16 feet tall and 20 feet thick.
Its walls are adorned with an inscription in Latin: “Benedictus Oui Venit In Nomine Domini” or “Welcome those who come in the name of God”, a testament to the island’s Catholic roots.
This is your chance to take in the beauty and history that this ancient entrance has to offer, as you make your way through Paseo La Princesa and into Old San Juan. It’s sure to be an unforgettable experience!
9. Plaza de Armas
The Plaza de Armas of San Juan is a stunning public square in the heart of the old city. It is located on San José Street and was designed to be the original main square of the city.
This plaza dates back to 1856 and features a beautiful round fountain with four marble statues representing the Four Seasons, originally placed in each corner of the square.
It’s an ideal spot for people-watching or taking photos.
10. Food trucks
Visiting Food Trucks is my favorite way to experience a new city. You’ll find food trucks throughout old San Juan that sell churros, drinks, Puerto Rican staples, and foods from all over the world.
In the Miramar Food Truck Park, you can eat from one of many food trucks, listen to music, and enjoy the bars too.
11. Calle del Cristo
Calle del Cristo is a charming and narrow street located in the center of Old San Juan. This street is lined with colorful colonial-style homes that have been preserved for centuries and are full of history.
It’s a great place to take a stroll through the city, as it provides stunning views of the surrounding architecture and nearby landmarks. From here you can visit the Church of Christ.
12. Soak up the Sun on Condado Beach
Condado Beach is only a 6-minute drive from the cruise port. This is one of the most popular destinations in San Juan, with a wide white sandy beach and stunning views of the Atlantic Ocean.
Here you can spend hours soaking up the sun, swimming in the clear waters, or just enjoying some relaxation time.
13. Cathedral of San Juan Bautista
The Cathedral of San Juan Bautista is a stunningly beautiful Roman Catholic church located in the heart of Old San Juan.
It was built in 1540 and is the oldest cathedral in the Americas. The facade and interior architecture are truly breathtaking, making it a must-see attraction for any traveler to the city.
The cathedral is also the final resting place of Juan Ponce de Leon the Spanish explorer who founded Puerto Rico in 1508.
14. Parque de las Palomas
Parque de las Palomas is a small park near Capilla del Cristo in Old San Juan. What makes this park unique is the hundreds of pigeons that are found here.
The birds expect to be fed, and will fly around you and even land on you with no fear. I’m not afraid of birds, but honestly, this was a bit much for me. There are SO many pigeons!
At the very least, you should walk by and check it out to see for yourself.
15. Stroll Along Paseo del Morro
Paseo del Morro is a scenic walkway located along the old city walls of San Juan. The path starts near the San Cristobal Fortress and follows the ramparts along the coast.
It offers stunning views of El Morro Castle, the blue waters of the Caribbean Sea, and the city skyline of Old San Juan.
Along the way, you’ll find many benches and alcoves to rest in while taking in the views.
This is an ideal spot for a romantic walk or some peaceful contemplation. No matter what your reason for coming here, Paseo del Morro will be sure to stay with you long after your visit.
16. Walk hand in hand on Paseo La Princesa
Paseo La Princesa is a stunningly beautiful promenade located in the historic city of San Juan, Puerto Rico.
Spanning along the walls of the ancient city and facing El Morro Castle, this walkway offers unparalleled views of the Caribbean Sea, as well as the vibrant skyline of Old San Juan.
The path is lined with trees and lamp posts, giving the walkway an even more romantic atmosphere. It’s the perfect spot to take a leisurely stroll with your significant other or to just sit and relax while admiring the stunning view.
Situated near the cruise ship harbor, Paseo de La Princesa stands as one of the world’s most picturesque city paths and is often sought out by tourists for sightseeing in Old San Juan.
17. Eat Mofongo
I know, food is taking up a few spaces in this list, but the food in Puerto Rico is yummy, and Mofongo deserves its own spot on a San Juan must-do list!
Mofongo is a traditional Puerto Rican dish that consists of a mashed plantain base and can be served with a variety of toppings. Plantains are similar to bananas but are firmer, starchier, and usually cooked before eating.
The mashed plantain base is known as “mofongo” and it is often served as an accompaniment to meat stews or seafood dishes.
It’s a must-try Puerto Rican dish, and you can find it in any restaurant in San Juan. So if you’re looking for an authentic taste of Puerto Rico, be sure to try some Mofongo!
18. Santa Maria Magdalena de Pazzis
Santa Maria Magdalena de Pazzis is a stunning and historic cemetery located in Old San Juan, Puerto Rico. It is home to the remains of many influential people, including Spanish governors and military personnel, as well as prominent locals from the island.
The cemetery itself has a long history that dates back to 1635 and is known for its beautiful and ornate architecture.
Visiting the cemetery is a great way to learn about Puerto Rico’s history and culture, as well as pay your respects to those who have passed away.
It has some of the most stunning views in Old San Juan and makes for an interesting day trip if you’re looking for something unique.
Explore the cemetery and you’ll quickly understand why it’s a favorite among locals and visitors alike.
To explore the cemetery you will need to walk or drive through the tunnel on Calle Tuburcio Reyes. Once in the cemetery, you will be right next to La Perla.
La Perla is a neighborhood that is known for its gang and drug activity. While the neighborhood became a point of interest to tourists after the “Despacito” video was filmed here, it is not recommended that tourists visit here.
If you do go, go during the daylight and be respectful of the residents. It is also recommended that you do not visit the cemetery at night.
If you don’t want to go down to the cemetery, you can get a great view of it from the walls of El Morro.
19. Visit San José Church
San José Church (Iglesia de San José) is a stunning and historic church located in Old San Juan, Puerto Rico.
Constructed on land given to the Church by the Ponce De León family in 1532, it was one of the first stone structures built in Puerto Rico and has survived for almost 500 years.
The church recently opened its doors to the public again after undergoing a massive 20-year restoration project. The beautiful architecture of the exterior and interior of the church make it a must-see in San Juan.
The ornate decorations, stained glass windows, and religious artifacts all add to its charm.
Visiting here is a great way to learn about Puerto Rico’s rich history and culture. Be sure to take the time to stop in and admire this stunning piece of architecture while you’re in San Juan.
Surfers, rejoice! San Juan is home to one of the most popular spots for surfing in Puerto Rico—La Ocho.
Located in San Juan and accessible from Escambrón beach, this area is ideal for experienced surfers looking to catch some waves.
Not too far from here lies La 8 Surf Shop, a great spot for board rentals and even surf lessons!
Whether you’re just starting out or an experienced surfer, La Ocho will provide some of the best conditions in the area for you to enjoy your time in the water. So grab a board and get ready for an unforgettable experience!
If you’re looking for an underwater adventure, Escambrón Beach is the place to go. This San Juan beach is home to an amazing artificial reef that was created back in 2009.
It features statues, caverns, caves, and elkhorn corals that have turned this area into one of the best snorkeling spots in Puerto Rico.
Visitors can explore the reef and enjoy a variety of colorful fish, coral formations, corals, and sea stars. Grab your Go-Pro and hit the water for an unforgettable day.
22. Kayaking and Paddleboarding
Kayaking and paddleboarding on the Laguna del Condado in San Juan is a great way to relax and enjoy some peace.
Choose from a variety of kayaks or stand-up paddle boards and take in the beautiful views of Old San Juan. There are also plenty of places to stop along the way so you can explore the mangroves and get a better look at the wildlife.
It’s an excellent activity for families or friends, as well as a great way to explore Puerto Rico’s history and culture.
23. Kite Surfing
You can learn to kite surf or show off your skills, at San Juan’s Balneario de Carolina beach. This spot is perfect for kite surfers of any level and even has two schools that offer lessons, rentals, and storage.
The warm waters and consistent winds make this a great spot to practice your skills or just get out on the water.
24. Resort for a Day
If you want to have the ultimate chill day, while visiting San Juan on a cruise, consider booking a resort pass for the day, where you can enjoy all of the amenities of the resort without having to book an overnight stay.
25. Find the Narrow House
If you’re looking for something off the beaten path, make sure to visit La Casa Estrecha (The Narrow House). This yellow two-story house is wedged between two standard-size buildings and measures 5 feet wide from wall to wall.
Originally just a narrow alley running into the center of its neighboring buildings, this pathway was eventually adorned with an elaborately designed ceiling and façade that enabled it to be transformed into a living space.
This unique building has become an icon in San Juan and is definitely worth a visit!
26. Watch the Sunset
Take in the stunning views of the city and ocean as you admire its architecture and watch the sunset over San Juan. It’s a fantastic way to end your day and experience the beauty of this city.
Things to do in Old San Juan Puerto Rico if you have more time in the City
If you have a few extra days in San Juan you can dig a little deeper into the city and experience things that are a bit further away too.
27. Dance in the Street to Live Music
Plenty of bars in San Juan have live music that you can enjoy on an evening out on the town.
While we were there, we were thrilled to hear live music on the street and to see people of all ages spontaneously start dancing and singing. It was so much fun!
28. Enjoy San Juan Bay
San Juan Bay is a stunning and historically important body of water located adjacent to Old San Juan, the capital city of Puerto Rico.
Spanning approximately 3.5 miles in length with an estuary of around 97 square miles, it is the largest bay in the region and serves as the home to Puerto Rico’s busiest harbor.
Its history dates back to at least 1508 and its stunning beauty can be taken in with a leisurely stroll along the bay or a tour onboard a boat.
29. Visit Isla Verde
Located just about 15 minutes drive from San Juan, Isla Verde is a popular place to spend the day enjoying the sun and sea.
Isla Verde is home to some of Puerto Rico’s best beaches, including Balneario de Carolina beach, which offers a host of activities such as snorkeling, kayaking, paddle boarding, and more.
With its crystal clear waters and gentle waves, it’s the perfect spot to spend a day at the beach.
30. Take a guided Food Tour
I love taking Food Tours! It’s such a fun and yummy way to get to know the city you are in and try new food, you may not order otherwise.
It’s also fun to take a cooking class and sometimes you can combine a market trip to see fresh foods and then cook, and eat them.
You could also make up your own food tour. We went to various food trucks and just asked them to make us whatever they recommended, and we had a blast! We also found a little hole-in-the-wall bar that made us a hamburger with mac and cheese on it, it was so yummy!
31. Relax on Beautiful beaches
There are plenty of beautiful beaches near San Juan that you can enjoy. If you have more than one day, you can choose multiple beaches to explore.
Some of the best beaches near San Juan are Playa Peña Escambrón Beach and Ocean Park.
Each beach offers something unique from clear blue waters to calm waters perfect for swimming. So you can find the perfect one that meets your needs!
32. Catamaran Trip
Taking a Catamaran Trip in Puerto Rico is a great way to spend the day. You can watch the sunset, or enjoy the warm Caribbean sun.
You’ll find tons of options ranging from group sailings to private charters. You can read more about Catamaran Trips in Puerto Rico by clicking here.
32. Take a Salsa Dancing Class
When traveling to Puerto Rico, one of the best ways to immerse yourself in its vibrant culture is by taking a salsa class.
Whether you are a beginner or an experienced dancer, learning how to dance salsa is an unforgettable experience that will help you connect with the local people and their traditions.
Not only is it fun and energetic, but it also provides an opportunity for self-expression and connection with your partner as you learn new steps together.
With its upbeat music and passionate movements, dancing salsa in Puerto Rico can be a truly transformative experience!
33. Stroll the Botanical Gardens
The Botanical Gardens of San Juan Puerto Rico are located in the heart of the city and offer a stunning display of exotic plants, flowers, and trees.
With over 289 acres of land to explore, the gardens feature lush rainforest-like vegetation and vibrant displays of color from flowers and plants.
There is no fee to visit the garden and it is open 7 days a week from 6 am to 6 pm.
34. Museo Las Americas
Museo Las Americas is an incredible place for visitors to explore the culture and history of Puerto Rico and other nations in the Americas.
Located inside the historic Cuartel de Ballajá, which served as a Spanish colonial military barracks, the museum features three permanent exhibitions that focus on the conservation and promotion of the cultural heritage of Puerto Rico
35. Museum of Contemporary Art
For those looking to explore the cultural heritage of Puerto Rico through its art, a visit to the Museo de Arte Contemporáneo de Puerto Rico (MAC) is well worth it.
Founded in 1984 in Santurce, the MAC is the only institution on the island devoted to exhibiting and promoting contemporary art and its issues. Here you can explore pieces produced since the mid-20th century in Puerto Rico and the Caribbean and Latin America.
The museum offers an engaging environment to learn about art through lectures, workshops, guided tours, and other events that promote dialogue between local artists, visitors, and other members of the cultural community.
36. See El Velorio at the Museum of History, Anthropology, and Art
If you’re looking for something truly unique, consider visiting El Velorio at the Museum of History, Anthropology, and Art.
This museum is considered one of Puerto Rico’s best-kept secrets and features a permanent exhibit with life-size mannequins dressed in traditional costumes representing the “Velorio” or funeral tradition that has been practiced in Puerto Rico for centuries.
Visitors to the museum can learn about this practice and its influences on the culture of the island, as well as how it has evolved over time.
There are also interactive elements throughout the exhibit that allow guests to participate and explore more deeply into this important cultural tradition.
37. Bar hopping
Old San Juan is a vibrant and colorful place to explore, with its cobblestone streets, picturesque plazas, and pastel-painted facades. And what better way to experience the city than bar hopping around town?
From traditional taverns that offer local craft beer and homemade food to modern rooftop cocktail bars with panoramic views, there’s something for everyone in Old San Juan.
Don’t miss out on the chance to experience all of the nightlife that Puerto Rico has to offer, and be sure to try some of the local specialties!
Things to do Near San Juan
If you have more than one day in Puerto Rico, you can venture outside of San Juan a bit and discover some new areas and experiences.
San Juan makes a great starting point for many tours.
38. Visit a Bioluminescent Bay
One of the best things to do in Puerto Rico is to visit a Bioluminescent Bay. While these bays arent in San Juan, if you have some extra time, you can take a tour that begins and ends in San Juan.
39. Take a Tour of El Yunique
El Yunique is a tropical rainforest located within the El Yunque National Forest. It is one of the most biologically diverse areas in Puerto Rico and offers stunning views, crystal-clear rivers, and plenty of outdoor recreation activities to explore.
Take a guided tour to learn more about its ecology and wildlife, take an independent hike along one of its many trails, or swim in one of the waterfalls you come across.
If you aren’t on a tour, you will need to make a reservation prior to your park visit.
40. Bacardi Tour
Finally, no trip to Puerto Rico is complete without a visit to the Bacardi Factory. Take this tour and learn the famous story of how Don Facundo Bacardí Massó created his own rum that would become one of the most recognized beverages in the world.
The tour includes a guided walk through the factory’s museum, a tasting of the different variations of Bacardi rum, and a visit to the gift shop.
Old San Juan History
Old San Juan is the oldest city in Puerto Rico and has a rich and vibrant history. It was founded in 1521 by Spanish explorer Ponce de Leon, who named it ‘Ciudad de Puerto Rico’.
The city was established as a major port of entry for Spanish ships and eventually grew to become an important military stronghold and trade center.
The city was attacked by the British twice during the 18th century and eventually captured in 1798. After Puerto Rico became a US territory in 1898, Old San Juan saw an influx of American influence, becoming home to many government buildings as well as universities and cultural centers.
The city also experienced an economic decline in the early 20th century, as it was no longer the main port of entry for goods to Puerto Rico.
Nevertheless, Old San Juan has persevered and today is a popular tourist destination thanks to its colonial architecture, vibrant culture, and numerous attractions.
Visitors from around the world come to experience the unique history and atmosphere of this historic city.
If you ever find yourself in Puerto Rico, Old San Juan is a great place to explore and experience the Caribbean’s rich history.
Where to Stay in Old San Juan
In San Juan, you can find modern upscale resorts, classic historical hotels, and private vacation rentals.
We stayed at Decanter Hotel and absolutely loved it. The hotel and rooms were gorgeous, our shower was wonderful (especially after a hot humid day of exploring), we had a balcony overlooking the streets, and the views from the rooftop were spectacular.
Hotel El Convento is also a popular choice. More than 350 years ago, this was a convent. Today, it is a beautifully appointed, romantic boutique hotel in the heart of Old San Juan.
If you are looking for an all-inclusive option, Caribe Hilton is a great choice.
Best Time to Visit Old San Juan
The best time to visit Old San Juan is from November to May, which offers the highest chance of sunny days and minimal rainfall.
June through October are the wetter months in Puerto Rico, and you can expect more frequent rain showers during this time.
Hurricane season is from June-November, so always keep that in mind. As you probably know from recent years, Puerto Rico is directly in the hurricane zone and has been devastated by storms numerous times.
Old San Juan has a tropical climate and temperatures remain relatively constant all year round, with average highs of around 86°F and lows of around 72°F.
Final Thoughts: Things to do in Puerto Rico
There are plenty of things to do and see in this captivating city. Take a stroll through its cobbled streets, admire the colorful buildings, visit museums that house works from local and international artists, and explore the vibrant nightlife.
Whether you’re a history buff or just looking for a good time, Old San Juan has something to offer everyone.
Do you need help planning your cruise, or land-based vacation? I can help you! I offer travel planning packages, and can help do the leg work so that you can enjoy your vacation!
Trip Planning Resources
These are companies I use and trust when planning all of our trips. I only recommend companies I personally use and trust.
⭐️Flight Deals: Expedia or WayAway
⭐️Airport Parking: Airport Parking Reservations
⭐️Rental Cars: Discover Cars
⭐️ Ferry Services: Direct Ferries
⭐️Hotel Booking: Hotels.com, Trivago
⭐️Things to do: Viator, or Get your Guide,
⭐️⭐️Travel Insurance: Travel Insurance Master
⭐️Theme Park Tickets: Getaway Today (use code FlipFlops10 for a discount)
⭐️⭐️Free Travel Planning Services: Flannels or FlipFlops Travel
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