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  • Home ยป Ultimate Travel Guide for a Trip to Old San Juan, Puerto Rico- What to do, where to stay and to eat

    Ultimate Travel Guide for a Trip to Old San Juan, Puerto Rico- What to do, where to stay and to eat

    Whether you are heading to Puerto Rico as a cruise ship stop or a full on trip to Puerto Rico, Old San Juan can not be missed! The historic district of Old San Juan is home to buildings as old as the 16th century. You might recognize Old San Juan for it’s brightly colored houses, cobbled streets, outdoor plazas, and fun nightlife. Keep on reading for the ultimate travel guide for a trip to Old San Juan.


    If you are on a cruise ship, obviously, this won’t apply to you. However, if you are planning on staying in Old San Juan for a few days then you definitely want to check out these options.


    • Sheraton Old San Juan Hotel– $194 per night- 4 stars hotel, waterfront hotel with a rooftop pool and a gym. The restaurant serves authentic Puerto Rican food which was highly recommended by the locals.
    • CasaBlanca Hotel– $159 per night- Absolute Old San Juan feels, Spanish-style hotel with a roof deck.
    • Hotel Milano– $93 per night- Located in the heart of Old San Juan, perfect to walk around town.


    • OSJ Ocean view for 6 people- $125 per night- Stayed at this one, excellent location, looks better in person compared to the pics.
    • Casa Moderna for 6 people- $59 per night- Fully renovated, another excellent option due to it’s location and best value for your money.
    • Colonial Old San Juan apartment for 2 guests- $99 per night- Love the colonial style, great reviews.

    Ultimate guide for Old San Juan, Puerto Rico. Everything about the town including where to eat, what to do, and where to stay. #travel #puertorico #oldsanjuan #oldsanjuanguide #whattodoinpuertorico


    So one thing you want to keep in mind, Old San Juan has lots and lots of cafes, restaurants, and bars. However, that does not mean they all are worth your time and money. Since it is a touristy area, I found some of the places not worth the money and the food was pretty blah. Avoid the tourist traps! Having said that, I have compiled a list of my favorite ones from my 2 trips to the island.


    • Mercado la Carreta– Excellent breakfast, they do offer brunch, lunch, a bar & tapas. A cute place and has a little market. Located in front of the La Barandilla Plaza.
    • Waffle-era Tea Room– If you are a waffle & tea fanatic, I recommend this place then.
    • Cafe Manolin– Inexpensive breakfast and lunch options offering local foods.


    • Raices– Open for lunch and dinner, the mofongo variations are to die for!
    • Cafe Puerto Rico– Another great lunch spot or dinner and has a full service bar.
    • Cayo Caribe– Heard really good reviews about their seafood.
    • Verde Mesa– Open for lunch and dinner, offers excellent Vegan friendly options. Caribbean & Mediterranean cuisine.


    • El Jibarito– If you are in search of authentic Puerto Rican food in Puerto Rico, then this is the place to be! The ambiance, the food, the service, everything is just amazing. If you take one recommendation from me, then go here! Expect wait times especially during dinner times.
    • La Princesa Gastrobar – Loved the ambiance, the only restaurant that has integrated in the menu recipes of a Puerto Rican cookbook published in 1879.
    • Pirilo Pizza Rustica– The most recommended pizza in town!
    • II Bacaro Venezia– Italian cuisine in a romantic atmosphere. Vegan options available.
    • La Madre– Modern Mexican restaurant with several margarita options and nightclub like decor.

    Dessert & Bars

    • Chocobar Cortes– Chocolate heaven! This place is about 2 blocks down from El Jibarito, I walked over in between my wait time for dinner, grabbed some chocolate and cake and made it back in time. Everything on their menu has chocolate, including drinks. I had the Chocolate Lovers Cake, probably inhaled it ๐Ÿ™‚
    • La Taberna Lupulo– Specializes in draft beer. 50 taps and 150 bottles of the finest Belgian, German, English, and American craft beers.
    • La Factoria– I was told it is one of the best bar on the island.
    • La Sombilla Rosa– Very happening place, great option for bar hopping.
    • Rivera Hermanas– Opens during lunch and stays open late till 2:00 AM.

    PRO TIP: I suggest taking it easy on the first day. I like to utilize this time to get familiar with the new place. I always find it challenging to find food the first day, so do some research before hand so you don’t starve then keep your itinerary open for the remaining days to explore and create your own unique experience.

    Ultimate guide for Old San Juan, Puerto Rico. Everything about the town including where to eat, what to do, and where to stay. #travel #puertorico #oldsanjuan #oldsanjuanguide #whattodoinpuertorico


    Old San Juan has a story to tell, a story that dates back to the 1500s! History is embedded in the city’s walls, and some of their traditions. While you enjoy strolling through this little city, take some time to learn about the significance of these historic buildings.

    • Castillo San Felipe del Morro– A $10 pass will give you access to this fort Castillo San Cristobal which is a few mins further. Castillo San Cristobal, is named in honor of King Philip II of Spain. The fort was designed to guard the entrance to the San Juan Bay, and defend the Spanish colonial port city of San Juan from seaborne enemies.
    • Capilla del Cristo is an 18th century chapel/museum located in the heart of Old San Juan. According to legend, the chapel was built to celebrate the miracle survival of a racer who leapt over the edge of the city wall, after he was unable to stop his horse. You will also find a pigeon park in front of the chapel.
    • Plaza de Armas– Historic town square located in Old San Juan. The square’s main feature is a round fountain with four marble statues representing “The Four Seasons”. There are some restaurants, cafes, a pharmacy, supermarket, and stores such as Marshalls.
    • La Fortaleza– Is the official residence of the Governor of Puerto Rico which was built between 1533 to 1540. Fortaleza street, which was also known as the Umbrella street, is located at Ca. de La Fortaleza, San Juan, 00901, Puerto Rico . Keep in mind, the umbrellas have now been replaced with the Puerto Rican flag which is still pretty cool for pictures.
    • Paseo la Princesa– This restored 19th-century esplanade is the place to begin your stroll through Old San Juan, because of its central location and its inexhaustible charm.
    • Cathedral San Juan Bautista– Is the oldest cathedral in the United States. A beautiful Cathedral is open to visitors. It is located on a busy street and can be missed easily.
    • Playa Peña Beach– My favorite beach around that area. There are several near by, however, they can get overcrowded especially if a cruise ship is in town.
    • La Placita de Santurce– This is where the party is! During the day, it is a market square where you can buy fresh fruits, vegetables, meats, etc., however, after 6:00 PM from Thursday to Fridays, the scene becomes fun and lively filled with locals and music. Several restaurants and bars are open late at night, and you can enjoy live music. Highly recommend visiting here.
    • Sunset cruise– Personally, I find that the best place for me to connect with people is during a cruise. Sounds weird I know, but this is when I am fully at peace, and relaxed. Whether you go to one during the day or sunset, I recommend checking this out. Click here.


    • Mar Chiquita beach– An excellent day trip option. I didn’t get to explore much of the area around, but it definitely seemed more locals accessed than tourists. You can spend hours watching the phenomenal waves hit the rock formation. I took an Uber from Old San Juan which cost me about $60 for a 45 mins ride, one way.
    • For another day trip option, I recommend renting a car via Thrifty and take a drive to the colorful town of Yaucromatic. Here you can explore town or head to Cana Gorda beach. It is about a 1 hour 40 mins drive from Old San Juan. The main beach entrance does close at 5:00 PM, however, if you keep driving further, you will find a private spot. Perfect to watch the sunset.
    • One of my recent trip to PR was during Thanksgiving break. Most of the businesses were closed on Thanksgiving day, however, several restaurants were still open that day. You might want to plan for a easy, walk around day.
    • Wear comfortable shoes in Old San Juan! The streets are made of cobblestones, the walkways can get bumpy. Not ideal for wearing heels.
    • Puerto Rico loves to party. There were fireworks in Old San Juan beginning Thanksgiving time and from what I heard they go on till then end of December. Parking is definitely a big challenge on the streets, use Uber if you plan to stay local.
    • Favorite parts of the trip: Puerto Rican food and Mar Chiquita beach.
    • Favorite parts- Mar chiquita beach and Puerto Ricon food. Least favorite: overspend in transportation.


    I have been to Puerto Rico a couple of times and have thoroughly enjoyed my trips. Old San Juan is a popular destination for the right reasons. I highly recommend visiting Old San Juan and exploring the remaining island. You will not regret it! There is so much history and culture waiting to be explored, oh and don’t forget the amazing food!


    Ultimate travel guide for a trip to Old San Juan, Puerto Rico. Everything about the town including where to eat, what to do, and where to stay. #travel #puertorico #oldsanjuan #oldsanjuanguide #whattodoinpuertorico



    1. November 6, 2022 / 10:10 am

      The houses by the beach are so cute! What a lovely lovely place with so much to see and do. You look great in these pictures! Awesome post!

    2. November 6, 2022 / 1:14 am

      Ok, you always have the CUTEST travel outfits! San Juan has been on my bucket list for ages, I definitely have to check out La Placita de Santurce!

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