Feature, Journeys
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One Weekend in Old San Juan

A weekend in Old San Juan is a weekend well spent. I never realized what a culturally rich and historic city Old San Juan was until I spent Labor Day wandering around the forts and photographing all of the colorful homes that fill the city streets. The days were warmer and more humid then I imagined, but as the sun set cool breezes swept over the city, brining everyone into the streets. In Puerto Rico they flaunt their curves, dress uniquely, eat hearty meals … and they are happy. The people are smiling, dancing, laughing. There is no stigma, no staring eyes, no expectations – and why should there be? As long as you have family, friends and cheap beer there really should be no worries. There were many lessons I learned from their hospitality, and that it’s ok to break out in a salsa dance anywhere and everywhere, but I also wanted to share my quick guide on what to do for a weekend in Old San Juan.

Airport: SJU
Currency: American $

Where to Stay: Airbnb

There are of course many hotels surrounding Old San Juan, but I am going to suggest staying at an Airbnb in the heart of town. Our accommodation was set up for guests and very clean, but the best part is we were 5 – 10 minutes walking distance from anywhere we wanted to go. There is a central square with a wonderful grocery store in town, which made it easy for us to stock up on beer, water and a few meals to cook for ourselves. Plus, how fun to have your own vibrant and colorful home in the heart of the city!
*Tip: Bring a portable blue tooth speaker and download Latin playlists from Spotify’s browse feature for local flavor.



DAY ONE: Sightseeing around Old San Juan

Discovering the history of Old San Juan was the highlight of my trip, possibly because I wasn’t expecting it! The Forts that protect the city are beautiful ruins, with endless nooks and crannies to explore. Expect to spend at least an hour at each fort.


  • As they are a part of the National Park system, there is an entrance fee of $5 per person. Make sure and ask for your receipt as it grants you access to the other forts/parks for five days!
  • Make sure to bring some bottle water – it’s hot out there! 

Start at Fort Castillo de San Cristobal. This Fort is on the North shore of Old San Juan, in the middle of the city with breathtaking views to the East and West of the city. It is the largest fortification built by the Spanish in the New World, covering about 27 acres of land – so there is more than enough to explore!

From here you can walk West on the path along Calle San Miguel / Calle Tiburcio Reyes road to arrive at your next destination.

Castillo San Filipe del Morro, which lays on the northwestern-most point of the island. The fortification was designed to guard the entrance to the San Juan Bay, and defend the Spanish colonial port city of San Juan from seaborne enemies. Like Fort Castillo, this old nostalgic Spanish fort is full of history and breathtaking views across the bay and the ocean.


By now you should be running up an appetite, from Castillo San Felipe del Morro, you can walk South into Old San Juan and wander through the cobblestone streets where you will see many places to stop by and grab a bite to eat paired with the local beer – Medalla.

From lunch, continue on to the south end of the city towards the West side of the island. There is a large Red gate at Puerta De San Juan, where you can enter a trail that runs along the water. This trail is called the Paseo de la Princesa, and was once used as a walkway for the Princess of Spain. It’s a beautiful walk on the water with statues and trees that hang over the waters edge. The south end of the path will loop back into the city where you can peruse trinkets being sold in the local markets.


Head to Calle Tanca (st.) to experience a magical street, where you have the option to pick up a drink from one of the bars surrounding the street or to bring your own and sit on the grassy nole across the street. Calle Tanca is alive with salsa music, and everyone is in a joyous mood, ready to watch the sunset over Castillo San Filipe del Morro.

For dinner check out El Jibarito. It’s not the fanciest food, but it’s wholesome, affordable and truly Puerto Rican. The line at the door can get quite long so plan an additional 30 minutes into your schedule. You will soon forget about the wait with a pitcher of Sangria!

Join the crowds around Plaza del Mercado for an evening with the locals and tourists alike. The bars reflect the vibe of the Brooklyn, NYC scene – cool cocktails and full beer menus, a bit of grunge paired with high octane spice. Some of our favorites include:
La Factoria – A neat spot with specialty cocktails – but don’t stop at the front of the bar – make sure and head to the back where you will find a door that opens up to two other bars in the back. Be ready for a night of salsa dancing!
La Taverna Lupul0 – A little more laid back, with an open air facade and a comprehensive beer menu – there is something for everyone.


DAY TWO: Get out on the water!

Start your day on the water with WOW Surf School. Your first day was spent touring the Forts inside and out, and with the jet ski tour you will have the opportunity to ride around the outside of Castillo San Filipe del Morro for an epic photo opportunity. The tour will also stop outside of Puerta De San Juan where you will have an opportunity to swim and learn more about the history from your tour guide. Of course there is plenty of time to thrash around the water on your jet ski – the trip lasts about an hour.
*Tips –

  • If you have trouble getting ahold of the school, shoot them a text. They do most of their business this way!
  • Don’t worry about missing the perfect photo opp if you don’t have a waterproof camera, they will take photos for you


Take the rest of the afternoon to enjoy a day at the beach, There are plenty to choose from that are near the city, including:

  • Ocean Park
  • Escambrom
  • Isla Verde

If you are there on a weekend, the beaches are packed with families – this isn’t your typical bring a chair and cooler type beach trip you might be used to. The locals set up grills, picnic tables, beach games, full course meals … we even saw one group with a generator, a laptop DJ station, and four huge speakers. The families will spend sunrise to sunset enjoying the beach and each other’s company. As it seems everyone brings their own food, we also discovered that most of the beach shacks only bring beer, so if you are planning on staying all day pack a snack – then grab a local beer and float the day away.


Make sure you plan enough time to head home and shower before sunset, where you will want to go down to the Paseo de la Princesa (Princess Walk) for an unforgettable view. The Princess Walk faces directly West and you will be able to watch the sunset behind the Bacardi Factory, as it lights up the bay with the brightest hues of oranges and red.
Walking back into town you will most likely come across a few street performers, and there is a wonderful Jazz Restaurant – Carl’s – where you can find the best Mojito in town. Take it outside to sit, sip and soak in the post sunset glow.

From here head up to Punto de Vista on the top of Hotel Milano. The restaurant is catered a little more to tourists, but the food is wonderful and the drinks are better. Grab a seat on the outside terrace, and stay as long as you like. Puerto Rico is known for their local dish Mofongo, and Punto de Vista’s is a must order. I suggest getting a shot of the Pitorro Rum (rum moon shine) – it’s a kick but the Tamarind flavor compliments the livelihood of the city and is great for sipping.





  1. Patsy Loveland says

    Sounded like fun on the go trip for the young at heart. I can see you in the travel Industry making a high splash. Love you. Aunt Patsy



  2. Victoria says

    Amazing post just moved here a year ago from New York. OSJ is my favorite place on the island and have not been to half these places. Thanks for sharing your fantastic weekend getaway!


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