Old San Juan, Puerto Rico – A Travel Guide

Living on a very small rock often requires a trip to somewhere slightly larger in order to maintain your sanity! As much as we love our little slice of paradise, occasionally you need to go to a place where nobody knows who you are… 


Only a 30 minute flight away is neighbouring Puerto Rico and a taste of the ‘big city’, with malls, highways, historical sites, museums, art galleries, cinemas and the occasional concert tour (even Madonna has toured here). 


I have visited Puerto Rico, in particular San Juan, a number of times during my years in the Caribbean – sometimes with the husband and often with my girls. 


After category 5 hurricane Irma hit us and then category 4 hurricane Maria pummeled Puerto Rico, life has been a little different and I was desperate to get over there and see how they were getting on! Finally I got the opportunity to visit this weekend and spent a happy couple of days getting my fix of Puerto Rican food, culture and hospitality. Sadly a few of my favourites have closed since the storms (physical damage and then a slow tourist season has made for really tough times in the hospitality industry) but I was thrilled to visit some of my old haunts and make new favourites on my trip this weekend! 


This post focuses purely on Old San Juan, you can read here for my suggestions on Condado, Isla Verde and other areas of San Juan and Puerto Rico… 

Featuring suggestions at a variety of price points, here are my top tips – my things to do, places to eat, where to go and what to see in Old San Juan, Puerto Rico:


The colourful buildings and cobbled streets –

One of my favourite things to do in Old San Juan is just to take a wander through the squares and streets. The colourful Colonial buildings are beautiful (I always like to pick favourites and imagine which one I would like to live in) and there are painted murals and bits of street art dotted around too. Stop for coffee, sit outside and people watch. There are lots of little coffee shops and bars where you can sit and pass the time, opportunities to rest your legs after lots of exploring, or ‘shopping breaks’ as I like to call them. 


El Morro and Castillo San Felipe del Morro –

Get up to the top of Old San Juan, take a stroll along the old fort walls and explore the castle ramparts. There are beautiful views of the ocean and locals ride their bikes and run along this stretch of the city – sometimes families will come up at the weekend to fly kites. 


Marmalade – 

My favourite restaurant in San Juan (if not the world) is Marmalade restaurant. Their tasting menus with wine pairings are a treat for the eyes and the tastebuds. Inventive, unusual and always with impeccable service. 

This is not a budget meal, but worth every cent – tasting menus start at $55 pp for three courses and go up to $85 pp for six courses. I recommend opting for four ($65) or five ($75) courses depending on your budget to give yourself the opportunity to sample lots of their dishes.  Save it for a special occasion, dress up and enjoy it.

Top tip – try the Global Warming cocktail pre-dinner, your margarita-based libation has a large ice cube made of chili water, the longer you take to drink it, the hotter it gets. 

Rosa de Triana

For a more budget-friendly meal, head to this delightful little tapas restaurant. Ask for a table outside in their little courtyard, lit with fairy lights for a really charming dinner experience. Most of the tapas dishes cost between $8-$12 so you can order a few to share. The tapas is traditionally Spanish, rather than Puerto Rican, and really delicious! 





La Taberna Lupolo – 

After your meal walk off your food with a climb up the hill to La Taberna Lupolo to avail yourself of their extensive beer menu – reading like a wine list there is a huge variety of lagers, bitters and IPAs all inventively named (yes, ‘Kilt Lifter’ I’m talking about you). This time I tried their rum punch, but even that was beer-related as it included hop oil! 

El Batey

A little hole in the wall dive bar – the interior of El Batey is completely covered in graffiti making for some interesting photos. More eclectic than the artwork are the regulars, stop a while and hear some stories. There’s a pool table and a jukebox and it’s right around the corner from Rosa de Triana, so if you went there for dinner this would be a natural spot for your post-dinner drink… 



El Convento

Not just a hotel but a piece of San Juan history, El Convento is known for its beautiful but quirky rooms. It also has a gorgeous tiled courtyard restaurant which serves excellent tapas for lunch and is well worth a visit, even if you decide to stay elsewhere. 

Hotel Casablanca – 

If you’re a fan of a cheap and cheerful, unique boutique hotel, this one is for you. Moroccan inspired decor with silver walls, four poster beds, lots of mirrors and tiled sinks can be found in the rooms – while downstairs in the lobby is decorated with giant chandeliers, huge orchids, original artwork and the film ‘Casablanca’ playing on a loop. Located right in the thick of it on Calle Fortaleza, street noise can be an issue. If you’re planning on any early nights keep this in mind and opt for an internal room (no windows means not street noise).  


Old San Juan is full of little boutiques and galleries, all of which are well worth exploring, but here are a couple of my personal faves. 

El Galpon

Selling genuine Panama hats, cigars and local artwork and with some of the best and friendliest customer service in the whole of Puerto Rico, stop in here if you want a quality sun hat that will last. 

(My El Galpon panama hat)

Pure Soul Boutique –  

Great fashion, jewelry, accessories and even some bath and body products can be found in this pretty little store, at Pure Soul Boutique. 


Salsa – 

When I think Puerto Rico, I think Salsa and nowhere is better to dance the night away than the Nuyorican Café just off Calle Fortaleza. Featuring live salsa music and a host of local dance partners just waiting to teach you the moves… 

Visit the art galleries – 

Old San Juan has a host of galleries and boutiques showcasing local art – but my favourite is Galeria Botello. Featuring sculptures and other artwork by Angel Botello alongside various international artists. 

Rent a bicycle –

For when you want to do more, see more, explore more and cram more into your day! What better way to get around the old city, but with a bicycle. There are a few bike rental places around, either rent the bicycle for the day or even take one of the guided bicycle tours – find out more here.

Have you been to Old San Juan? Do you have any tips or suggestions for me to try out next time I visit…?



    • thebarefootangel
      May 25, 2018 / 9:11 pm

      Thank you! Yes, so lucky! So beautiful and so much fun to visit!

  1. June 1, 2018 / 12:58 pm

    When I was last in Puerto Rico It did NOT look this nice! I will surely take these tips with me next time I go! Beautiful Pictures! And that Top Tip Global Warming Cocktail sounds AMAZING!

    • thebarefootangel
      June 1, 2018 / 1:00 pm

      Sorry to hear that Lacy, when did you visit? Was it right after the hurricane? That storm definitely messed things up! Glad you liked the post! X

  2. June 20, 2018 / 9:53 pm

    Puerto Rico looks amazing! Your photos are beautiful! I have never been to Puerto Rico but I’d love to go! Thanks for sharing!

  3. June 20, 2018 / 9:56 pm

    Wow! The sights are amazing and the food looks so so good! Great guide 🙂

  4. June 20, 2018 / 10:25 pm

    It has been years since I have been to San Juan it is a cool place. A bit on the expensive side but worth the visit. Your pictures and tips have really inspired me to go back =)

  5. Priyadarshini Rajendran
    June 21, 2018 / 4:46 am

    Very useful guide, saving this for my upcoming Puerto Rico trip.

    • thebarefootangel
      June 21, 2018 / 10:42 am

      Oh my goodness, you are going to have such a fantastic trip!! I’m jealous as I want to go back!

  6. June 21, 2018 / 9:39 pm

    What a beautiful city! I love all the architecture!

  7. Josie
    June 22, 2018 / 6:37 am

    Oh gosh it looks stunning! I’ve always wanted to visit purto Rico

  8. July 21, 2018 / 1:20 am

    Such a beautiful and cool place. I would love to visit Puerto Rico. I think I would need to get one of those hats, and I would love to salsa!

  9. July 22, 2018 / 4:18 pm

    I LOVE THIS! Your pictures are great. Funny, I have some of the same images from our trip. The black door, I stumbled upon and stood there for the longest time snapping pictures. My family met me for lunch and I took them back for more images. That façade was stunning! I love it there.

    • thebarefootangel
      July 22, 2018 / 4:55 pm

      Yes, we found it by accident too! Such an iconic building though, now that we’ve found it we’ll be sure to go back! 🙂

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