A few notes about Old San Juan:
You can take a free trolley around town if you’re tired of walking.
It gets really (annoyingly) crowded when multiple cruise ships dock. It’s like a quiet little city then BAM, ten thousand people disembark and flood the tiny little streets.
The weather is pretty consistently 85 degrees or so.
It’s safe and walkable and tiny enough to walk the entire city rather quickly. Though your feet might hurt because cobblestone.
Where to stay in Old San Juan:
Sheraton Old San Juan – We stayed in Old San Juan this time because last time we stayed a few miles away at an Airbnb apartment and ended up taking the bus there every day. This was way more convenient (except for parking). It’s not big or fancy but it is super close to everything. We stayed here because the location and because I got a discount on one of the travel sites, making it the only hotel I could find under $200 a night. Done.
What to eat in Old San Juan:
EVERYTHING. EAT IT ALL. We use Yelp to find good food (and Fodors). (My personal travel eating rules are: eat something you can’t get at home. If they have a guava option – or whatever is local to where I’m traveling, get it. Drink coffee at as many different places as possible. Get a cocktail when I’m eating out even though I’m always too cheap to at home.) (And specifically in Puerto Rico – sit outside! It’s winter at home!)
La B de Burro – This was our first and last stop on the island. We got our car, drove here, then drove out to our resort. Then, on the last day, we left our hotel in Old San Juan, drove here, and drove to the airport. Caramelized plantains in the veggie quesadilla = my last meal .
La Madre – Fancy Mexican food. The queso and vegetarian burrito was were both superb. I didn’t care for my coconut margarita, but Mike’s guava margarita and Gabe’s watermelon juice were both fantastic! And then we had guava cheesecake in tortillas for dessert and it sealed the deal – a great restaurant. (And the only meal we had in peace as Theo slept in his carrier the entire time. Hallelujah)
Casa Cortes ChocoBar – we went here, um, three times. THREE TIMES. It was all amazing and excellent and full of chocolate-laced everything. From chocolate grilled cheese to a strawberry frozen hot chocolate to croquettes you dip in dark chocolate and Sriracha, I just could not get enough of this! I felt like I died and was living in Chocolat.
Cafe Berlin – our favorite sit down restaurant in OSJ – amazing food and tons of vegetarian options. They were also beyond kind to us even when our baby started shrieking loudly. We felt bad, so we moved outside to the (loud!) dining area on the street. They kept assuring us we didn’t have to and were bothering no one, though.
Cafe Cuatro Sombras – Get a latte (iced or hot!) and guava jam toast. Very good breakfast and you can watch them roast coffee beans on site.
Caficultura – the best cafe con leche we had! Oh, it was so good. (We also had coconut french toast.) And our server made us speak Spanish, which I appreciated! (She spoke English, but was kind of like our teacher and made us use what little we had to communicate.)
What to Do in Old San Juan
Castillo de San Cristobal and Castillo del Morro – Aside from eating and just walking around (soaking up SUN! and WARMTH!),
Walking tour of OSJ – We used the Fodor’s book we got from the library as a guide, but this or this looks pretty similar. It did get super hot walking around the wall that protected the city in colonial times, so be sure to bring water!
Balneario de Carolina [Carolina Beach in Isla Verde] – (This is not really in Old San Juan, but the closest nice beach!) Like I mentioned, we’re not huge hang-out-at-the-beach people, but we did enjoy a few hours on the way from our resort to Old San Juan on a public beach that we had all to ourselves. It was gorgeous! Parking was $4, which was not much for the great amenities and having so much space to enjoy the ocean and beach. The Ocean Park and Condado beaches are great – but they were much more crowded. (Also, we went the beginning of February – a generally less crowded time, I think.)
Whew. And that’s our trip! I hope this sharing is helpful to someone. If only myself in 2 years when we plan to go back… :)
