10 Must See & Do Activities When Visiting Old San Juan PR

The list of must see and do things while in Old San Juan, Puerto Rico is limited only by the length of time you have to spend in this exciting Caribbean city. To help you plan your visit we have put together a list of our top 10 favorites to get you started! Old San Juan is a colorful, vibrant Caribbean city full of life and activity. Stroll the streets, visit the forts, take a free trolley, shop, eat, drink and enjoy salsa music and dancing in this historic colonial city that is rich in old world European charm.


1) Stroll the Colorful Streets of Old San Juan



Brightly painted buildings Old San Juan PR

The brightly painted buildings along the streets of Old San Juan combined with the colorful tropical flowers are truly inspiring. Shopping and sightseeing are a great way to spend your day as you walk along these charming streets.



Tropical colors Old San Juan PR

Tropical colors can be seen everywhere in Old San Juan. There are over 400 restored 16th and 17th century Spanish colonial style buildings in the 7 square blocks of this historic area. A free trolley service runs 7 days a week and makes frequent stops. You can hop on and off at any of the trolley stops.



Colorful Steep streets Old San Juan PR

The colorful streets in Old San Juan can be steep. It’s a good idea to start your sightseeing early in the day and pace yourself as it can get very hot in the summer. Be sure to wear a hat, drink plenty of water and use sunscreen.



Narrow cobblestone paved street Old San Juan PR

The narrow streets in Old San Juan are paved with blue cobblestones. The cobblestones were originally used as ballast for the trade ships arriving from Spain. The blue building at the end of the street is La Fortaleza. It is the oldest governor’s mansion still in use in the Western Hemisphere and part of the old city’s World Heritage Site.


2) Explore the Historic Forts of San Juan


Castillo San Felipe del Morro



Castillo San Felipe del Morro Fort Old San Juan PR

The Castillo San Felipe del Morro Fort was built by Spain to protect the city against attacks along the coastline. Construction of El Morro began in 1539 with many of the walls being added from the 1760’s -1780’s. The fort rises 140 feet above the sea and is made up of 6 massive levels. The different levels include the barracks, dungeons, ramps, towers and tunnels. You can explore the fort on a self-guided tour at your own pace. The forts are part of the San Juan National Historic Site and are administered by the National Park Service.


Castillo de San Cristóbal



Castillo de San Cristóbal Fort Old San Juan PR

Castillo de San Cristóbal Fort was built by Spain to protect the city of San Juan against land attacks. It is the largest fortification built by Spain in the New World. When it was completed in 1771 it rose 150 feet and wrapped around the entire city of San Juan. The views from both forts are incredibly beautiful. With more than 400 years of history, the forts are the oldest European style fortifications within the territory of the United States. You can take the free trolley between the two forts.


3) Enter the City Gate of Old San Juan



City Gate Old San Juan PR

This city gate to Old San Juan still stands proud today. There were originally 6 gates in the wall that surrounded the city to protect it from attacks; this is the last remaining gate. Centuries ago the huge wooden doors would be closed at sundown to protect the residences of the city. The path along the water to the left outside the old city gate will lead you to the Paseo de la Princesa. This lovely tree lined promenade has gardens, a restaurant and usually some vendors. Walking through the gate will lead you to the heart of Old San Juan.


4) View the Sculptures & Statues of Old San Juan


La Rogativa Sculpture in Rogativa Plaza



Plazuela de la Rogativa sculpture Old San Juan PR

Plazuela de la Rogativa is a small plaza featuring a bronze sculpture overlooking the Bay of San Juan. According to legend, the bishop and the women of the town formed a procession and frighten away British troops during the 1797 attack on the city of San Juan. Carrying torches, singing and ringing bells as they walked through the streets the British mistook them for large troop reinforcements and decided to sail away. The view of San Juan Bay and the city wall from the plaza are outstanding.


Raices Fountain & Sculpture Along Paseo de la Princesa



Raices sculpture fountain Paseo de la Princesa PR

Raices is a dramatic fountain and bronze sculpture located at the western end of the Paseo de la Princesa. The sculpture represents the islands heritage and cultural roots. It is an excellent spot to sit, relax and watch the sunset in Old San Juan with a beautiful view of the harbor.


Four Seasons Fountain at Plaza de Armas



Plaza de Armas City Hall Old San Juan PR

Plaza de Armas, located on San Jose Street, was designed to be the main square of Old San Juan. The fountain in the center of the square features four 100 year old statues known as The Four Seasons, each statue representing a different season. City Hall can be seen in the background. Plaza de Armas remains today as a central gathering place. Children love feeding the pigeons there.


5) Visit Capilla del Cristo



Capilla del Cristo chapel Old San Juan PR

Capilla del Cristo, located at the end of Calle Cristo, is a small chapel built in 1753. Inside the chapel is a small silver altar which was dedicated to the Christ of Miracles. The wrought-iron gates are usually closed but you can view inside the chapel through the gates. There are many versions to the legend that led to the construction of the chapel. One version states in 1753 a young horseman raced down Calle Crsto and fell to his death plunging over the steep cliff. Another declares that he miraculously survived the fall and yet another version tells that the horse amazingly stopped just before tumbling over the cliff. Maybe we’ll never know the true story behind this legendary chapel.

To the right of the chapel is Parque de las Palomas (Pigeon Park). You can purchase food to feed the pigeons there or just sit and enjoy the magnificent view of the harbor and mountains in the distance.


6) Enjoy the Food of Puerto Rico



Food Dinner San Juan PR


Pastry Dessert San Juan PR

Food in Puerto Rico is a treat and good food can usually be found in small cafes and street vendors for a very reasonable price. Some of the more traditional foods are roast pork, mofongo, plantains, yucca, rice and beans. Try them all if you have the opportunity…I bet you will walk away happy! Don’t forget to try some of the amazing bakery treats you will find in almost any restaurant in Old San Juan.


“SOFO” Culinary Fest on South Fortaleza Street



Culinary Fest Old San Juan PR

The Culinary Fest held on South Fortaleza Street in Old San Juan is an event not to be missed! We try to plan our trips to Puerto Rico around the announced date for this event although it can be hard to get an exact date well in advance.



Culinary Fest South Fortaleza Street Old San Juan PR

During the Culinary Fest Fortaleza and nearby streets are closed to traffic so dining and dancing in the streets can be enjoyed. It’s a culinary street party that’s hard to beat.



Culinary Fest Parrot Club Fortaleza Street Old San Juan PR

The Parrot Club along with approximately 40 other participating restaurants set up booths offering their specialty dishes and drinks. Drinks are made to order and food can be sampled sitting down or taken with you to enjoy as you walk along checking out the next booth! This is a great way to taste the food from some of Old San Juan’s trendiest restaurants. There’s live music, dancing in the streets, lots of eating and an all around good time during the “SoFo” Culinary Fest.


7) Visit Cathedral of San Juan Bautista – San Juan Cathedral



Cathedral of San Juan Bautista Old San Juan PR

Cathedral of San Juan Bautista in Old San Juan is the second oldest Cathedral in the Western Hemisphere. Built in1540, it is over 450 years old. The medieval architecture and exquisite artwork on the ceilings are outstanding. Ponce de Leon, the Spanish explorer, which we referred to in our post St. Augustine Florida Celebrates 500 Years of History, was the first Governor of Puerto Rico and is entombed here. The Cathedral is open daily and Mass is still held here.


8) Visit Santa Maria Magdalena Cemetery



Santa Maria Magdalena Cemetery Old San Juan PR

Santa Maria Magdalena Cemetery in Old San Juan is the most beautiful cemetery we have ever seen. It is located just outside the walls of Fort San Felipe del Morro fort directly on the Atlantic Ocean. Constructed in 1863, it is the final resting place of many of Puerto Rico’s most prominent natives and residents. The headstones and sculptures in this cemetery are exquisite works of art. It’s amazing to see the way the artisans were able to convey emotions in their sculptures. The cemetery is open to the public although we have found the gate to the entrance sometimes closed. You can still view the statues through the fencing.


9) Try a Hand Made Cigar



Hand made cigars Old San Juan PR

Try a hand made cigar while you are in Old San Juan, Puerto Rico and be sure to bring some home to share! This vendor sells hand made cigars made from Puerto Rican and Dominican tobacco leaves.


10) Enjoy Local Music & Dancing


Salsa Dancing at Nuyorican Café



Nuyorican Cafe Old San Juan PR

The Nuyorican Café is the place to go in Old San Juan for live music, salsa dancing and a true taste of Puerto Rican culture. Popular with locals and tourist alike the atmosphere here is lively and fun! The café is tucked away in an alleyway off San Francisco Street just below Da House hotel which adjoins the cafe. Da House hotel is where we always stay when we are in Old San Juan.


Live Music and Dancing Along Paseo de la Princesa



Paseo de la Princesa music singing dancing Old San Juan PR

Paseo de la Princesa near the cruise ship docks is where you can find live music on most weekend nights and holidays. The band plays local music, singers entertain and couples enjoy dancing. The street is lined with vendors selling food, drinks and souvenirs. It’s a great way to end your day in beautiful Old San Juan.


Puerto Rico day trips from San Juan:

Arecibo Observatory in Puerto Rico Celebrates 50 Years
Rio Camuy Cave Park
Guavate, Home of the Lechon
Culebra Island – Puerto Rico’s Little Paradise


We’d like to hear from you!

Have you visited Old San Juan? What gets your vote for the best things to see and do while there? Let us know in the comments below.


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  1. sarah chambers

    Is there any special fest or celebrations go on 1/25 and 1/26/2016

  2. sarah chambers

    Staying at Sheridan,old sanjuan 1/25/2016 and 1/26/ leaving on a cruise on the 27 tbhey said there are trolly by the hotel where do they take you what is the furthest place they go. Thank you

    • Hi Sarah, the trolley service in Old San Juan is free and makes frequent stops so you will be able to enjoy the sights, shopping and restaurants in Old San Juan pretty much as you please. I have provided the link below to a website that will give you all the details about the trolley service and a map to the stops that the trolley makes. Have a great trip!


  3. Lisa

    These look like great ideas. Are most of these places within walking distance of where the cruise ships dock? We will be there on a Saturday from 3 PM until 11 PM. We’ll have our 12 year old with us, so we probably won’t stay that late if he gets tired with all the walking. Thanks!

    • Hi Lisa,
      For the time frame you mentioned, I would recommend sightseeing the streets of Old San Juan and the historic forts. This makes for a great historic visit of Puerto Rico and you can hop on the free trolley for easy transportation between the forts and Old San Juan. Our 12 year old loved the forts! Enjoy and let us know how your trip went!

  4. kesha mcelhaney

    Hello what is there to do with kids any suggestions planning a trip there

    • Depending on their ages, I think the historic forts in Old San Juan would be of interest to children. Younger children may not enjoy the forts as much as the older ones would. The beaches are fun for children of all ages. Luquillo Beach is particularly well suited for families with children with all the amenities for enjoying a great day at the beach. I would check out Puerto Rico Day Trips website at http://www.puertoricodaytrips.com/ for suggestions on planning your trip, they have tons of useful info on Puerto Rico. Have a great trip!

  5. Devon Anderson

    Hi Barbara,
    My boyfriend and I will be travelling to San Juan during our spring break, which is the end of February/beginning of March. We are both college students, and I was wondering if you have any good ideas/places to see/tips for younger travelers like us. We already have plans to go on a tour of the Bacardi Factory and visit El Morro and El Yunque. We will be staying for 6 days, so we have plenty of time to fit in a ton of things!
    Interested to hear what you might recommend!

    • Sounds like you have already made some good plans for your trip to Puerto Rico. If your plans are for spending time in Old San Juan a visit to the historic area with all its beautiful and colorful buildings, food to sample and local music can be fun. Around the cruise ship docks on some nights you can find many vendors with food, drinks and plenty of local music to enjoy. The Nuyorican Café located in an alleyway off San Francisco St. in Old San Juan can also be a fun place to spend an evening salsa dancing with the locals. The café is located next to Da House Hotel which makes a nice place to stay after an evening of partying. You can read our review of Da House Hotel here. Hope this helps…have fun!

  6. We were fortunate enough to visit and experience Old San Juan with some friends of ours that had already been there a few times before. It is an absolutely wonderful town and community with so much beauty (I love the colorful houses) and so rich in history! We were only there for 2 days before we set sail on our carribbean cruise which was also great but I’d like to come back to just take in more of Old San Juan. It was back in Oct.’14 when we we there but I’m just now finding this particular site. And ohh yes,DELICIOUS FOOD!!!! :-)

    • What a great account of your first visit to Old San Juan. And so nice that you were able to visit with friends that had already been there. I totally agree…wonderful town, community and food!! Like you, we find ourselves planning our next trip to Old San Juan right after we return from our trip there.

  7. vanessa Wright

    love your site – my 4 adult children and i have decided on san juan for a 2015 vacation destination we have never been so really looking forward to it. id like to go in june during the sofo culinary week, i’d prefer to rent a house or condo for the 5 possibly 6 of us. im a single mom paying so cant go super expensive ive spent 1200.00 for a week on the beach in clearwater so somewhere around that price or maybe a little more would work- any ideas. hopefully we can rent bikes to get around. thanks so much

    • Hi Vanessa, and thank you – we’re happy to know you’re enjoying out site. The sofo culinary fest is so much fun. If you’re lucky enough to be in Old San Juan during the culinary fest you and your family are sure to enjoy the authentic Puerto Rican food, drinks and music. It can all be sampled on the designated streets in Old San Juan. As far as accommodations, we always travel from place to place after a day or two not really staying longer than that. Because of that I don’t have any first-hand experience with renting a house or condo in Puerto Rico. I hope you have a great trip!

  8. Tracee

    Hi Barbara,

    Thanks so much for your post! My boyfriend and I are headed to PR on 4/20/15 for our ten year anniversary. Do you have any suggestions for romantic activities/restaurants? Also, are there any nightlife strips that you would recommend?

    Thanks again!

    • Hi, Tracee and congratulations on your 10 year anniversary! In Old San Juan the Nuyorican Café, tucked away in an alleyway off San Francisco Street, is a fun place at night. The cafe has a lively atmosphere with great music and salsa dancing. It adjoins Da House Hotel on San Francisco Street which is a nice place to stay if you book a room away from the noise!! Just ask the staff before you book which rooms they would recommend for less party noise and they can advise. Have fun!

  9. thanks for the post… very lovely and useful.
    we will be in port for 1 day. is there a self-guided walking tour that you can recommend? or, alternatively, can you recommend how to plan our day?

    • Thank you, Peter. There are many options for spending your 1 day in port; all of which should prove to be enjoyable. I would start at the Visitor Center of the Puerto Rico Tourism Company in Old San Juan. They have recently moved to a new location which is on the first floor of the Ochoa building located just across the street from Pier 1. It’s just a short walk from the cruise ship piers and they will provide you with helpful information as well as maps for the self-guided walking tours of Old San Juan and of course other options you may enjoy for your day. If this is your first time to Puerto Rico I think I would start with a visit to the forts and also the walking tour of colorful Old San Juan if time permits. Don’t forget you can hop on the free trolley service that will take you from one location to another without spending so much time walking from sight to sight. Have a great trip and remember – we would love to hear about your experience when you return.

      • Thanks for your quick reply, Barbara.
        A couple of questions, if you don’t mind…
        – Do you recommend to visit BOTH forts, or “you’ve seem one, you’ve seen them all”? and if one, which would you recommend?
        – Is there enough time in 1 “day in port” to cover your list of 10 must see sites? and is your list in order of priority?

        I think that’s more than a couple :)

        many thx


        • You’re welcome, Pete. Although both forts are amazingly beautiful and rich in history I think I would pick one because of the size of the forts and the amount of walking you will be doing in just one day. My favorite is Castillo de San Cristóbal because of the underground tunnels you can walk through and the ancient graffiti still visible on the dungeon walls. Most of the sights on my list are within the walking tours of Old San Juan, so yes, you should be able to cover most of the list. That is with the exception of the activities that are only available during certain times of the year such as the Culinary Fest and the evening activities such as the salsa dancing and the live music near the port. My list is pretty much in order of what I would call priority – but all are absolutely worth seeing. Keep in mind that this will take a lot of walking and time even when using the free trolley service. I would recommend wearing sunscreen, a hat, comfortable shoes, and taking water with you. Be sure to plan your day according to the amount of time you have in port. I hope this helps plan your trip. Have fun!

  10. Israel Tutson

    I am surprising my wife with a birthday trip to San Juan on 04/17/14. I am planning our itinerary and am interested in the day trip to the caves. Is there transportation from San Juan to the Caves? or do we have to rent a car?

    • Happy Birthday to your wife, what a great surprise you have planned for her! As far as transportation to the caves goes I know there are tour guide companies in San Juan which will provide complimentary pickup and drop off from most San Juan hotels. Check with your hotel on their recommendations. I don’t have any first hand info on any of them for you because we always rent a car while in Puerto Rico. We like to travel all over the island and having a car is the best option for us. Have a great trip!

      • Israel Tutson

        Hello Again,
        With that being said, I think we will rent a car! Can you refer us to the best place for a car rental once we get to Puerto Rico? Our hotel is in Isla Verde. Any car rental tips? Thank you! :)

        • We rent from the Budget or Dollar and just take the shuttle bus from the airport to the car lot that is provided free by the rental car company. Driving can be a little tricky in Puerto Rico and the rental cars are not always in the best of shape. Directions will be by landmarks rather than street names. Be sure you’re ok with this before rented a car. Another option is your hotel, they may have cars available to rent on site, check with them. Or you still have the option of tour companies for the day trips you chose. We are very adventurous and like to venture out on our own so we have a great time exploring in Puerto Rico. I hope this helps.

          • Israel Tutson

            Thank you so much! I appreciate it… I’ll come back in a couple weeks and leave a comment about how it went! :)

          • You’re very welcome and I look forward to hearing about your trip!

          • Yari

            Hi Barbara! When you are staying at da house hotel where do you park your rental car?

          • If you don’t find parking on the street near the hotel (and you usually won’t) there is a large multi-level covered public parking garage near Da House Hotel. We pull in the front of the hotel to unload our luggage first which the staff will help you with then we continue to the garage, it’s a fairly short walk back. The staff can give you directions to the garage, they are very helpful.

  11. Deborah

    Beautiful photo’s Barbara and such interesting places to visit. Thank you for your suggestions; I can’t wait to visit!

    • Your welcome, Deborah! Old San Juan is full of beautiful and interesting things to see and do. I’m sure you will love all of the tropical beauty there when you visit!

  12. Eye pleasing and amazing photos of wonderful places. Glad to know and read this informative post. Surely will like to plan to visit. Many thanks for sharing.
    Angela – Wine Tours Napa recently posted…Whale-Watching Along the Northern California CoastMy Profile

    • Old San Juan is full of interesting sites, I hope you get to visit this historic city and enjoy it the way we have.

  13. We were just in Puerto Rico for the holidays. I love walking thru Old San Juan and admiring all the buildings. Did you go to the Pigeon Park (Parque de las Palomas)? Great post..

    • Hi Carmen, and welcome to our site! Old San Juan must have been a great place to spend the holidays. Yes, we did go to Pigeon Park next to Capilla del Cristo chapel. I was shocked at how many pigeon were at the park. They really look comfortable though the way some of them huddle down in the holes in the block walls there.

  14. Good tips! I would love to visit one day:)

    • Ciki, I hope you are able to visit Old San Juan, I think you would enjoy all things that are there to see and do!

  15. Color, history, beaches, bars and full of culture, San Juan is now on my bucket list. Thank you for the post.

  16. Stunning photos, Barbara. Old San Juan, Puerto Rico is such a colorful city. I bet it’s easy to soak up the Caribbean vibe, even without a lot of sightseeing! (Although I’d be hard-pressed to stay in one place for long. Too many great ideas on this lis!)
    Carrie Kellenberger recently posted…Photo Essay: Where I Traveled to in 2013My Profile

    • Thanks, Carrie! That’s so true, just being surrounded by the sights and sounds of Old San Juan can put you in the Caribbean frame of mind!

  17. Looks both beautiful and interesting! :-)
    Becky Padmore recently posted…Top 10 cool and unusual hotels in Cape TownMy Profile

    • Hi, Becky! Old San Juan is indeed both beautiful and interesting, we always enjoy exploring while we are there!

  18. I adore all the colorful streets. I’m pretty sure I would be content getting lost amongst them.
    Annette | Bucket List Journey recently posted…Visit a Maasai Tribe in Tanzania, AfricaMy Profile

    • My thoughts exactly, Annette! I think we have gotten happily lost a time or two strolling the streets of Old San Juan.

  19. Sounds like I need to plan a visit for Culinary Fest!! Great article…
    Val Dawson recently posted…My book is out!! Dream Catcher: The Magic Of Living Your Dream LifeMy Profile

    • Hi Val, I think you would really enjoy the food and fun atmosphere at the Culinary Fest. If it meets with your schedule it is definitely a must do when in Old San Juan!

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