Select Page

It just so happens that our buddies on Nightingale Tune are drastically more sophisticated and posh than this country mouse and city mouse here on Selah. They are New York city folk and let me tell you – they can cook like none other. It helps that Lauren is a professional chef and also a sommelier…yeah, told you they were cooler than us.

Alas, they have looked past our mac n cheese eating ways and we have become quite the traveling pals. Hopping in a rental car and touring San Juan was a no brainer when we realized the weather was going to keep us hostage in Puerto Rico for a few extra days. We were eager to continue pressing east to the Virgin Islands, but also wanted to make sure we squeezed every ounce of fun out of Puerto Rico. We truly feel like we have seen this island and love it more and more.

We had zero expectations for Old San Juan except to sleep in a hotel bed and have a hot shower. Everything else was gravy. Bo and I have a history of failed city explorations, so we were more than happy to let someone else handle the tour planning. Bo is an incredible navigator and I am exceptional at having unfounded, crazy opinions, so we did bring something to the table – but not much. Lauren mentioned that they liked to eat and wander, and it sounded perfect to us.


A brief synopsis:

Cafe con leche with Mallorcas. Honestly – I am not totally sure what is all involved but sweet bread, jam and cheese and don’t EVER turn one down. A most delicious start to our day.

We literally chugged our coffee and walked directly into a wine shop, La Boutique Du Vin. They didn’t offer tastings, but would be happy to sell us a bottle of champagne and a cheese plate – how could we turn that down?  Did I mention it was 11am?

The only reasonable next step would be Paletas!  Paleta is the spanish word for fancy popsicle and after a few wrong turns we had earned ourselves a little treat. Bo and I shared a fancy oreo popsicle and were not disappointed; how they fit an entire oreo in there I will never know.


From there we vowed to walk a while to polish off a few calories. We had absolutely glorious weather with cloudy skies and breezy conditions – which made the walks totally doable and even fun.

No stop at a National Park is complete without shaved ice and Bo was happy to oblige. The rest of us took a pass. We wandered down hill to find a tapas spot and were not quite successful, so we ended up at Bootys. Probably not an official “foodie approved” stop, but we did have an incredible Mojito.

Have you ever seen someone so pleased with his snowcone purchase?

Have you ever seen someone so pleased with his snowcone purchase?

Naps were in order after all that eating and we agreed to rendezvous a few hours later for an epic dinner. Nearly everyone we ran into or asked or facebooked said we HAD to go to La Factoria for dinner.  We have learned that if you hear the same recommendation from multiple people you listen – and we are so glad we did.

I didn’t get any good pictures because it was dark, moody lighting, but we had an incredible meal in a fabulous stop. Well worth the hype if you are ever in San Juan. We stumbled back down the hill to our hotel in a full-blown mood coma and crashed into the cool, crisp hotel sheets.

But don’t worry, the food tour is not over just yet. Before we set out on an epic day of errand running we needed one last brunch. For me I think it was my most favorite meal of the trip. Bo and I woke early and had a pre-brunch coffee and a darling little spot, Cuatro Sombras. While we love our Aeropress on the boat, nothing beats a well-crafted cafe con leche.


We strolled on to brunch with Brian and Lauren at Caficultura.  I am not really a breakfast person and usually would prefer to spend my calories and cash on meals that include desert, but this is a place I would not miss. The menu genuinely had 10 items we all wanted and deciding what to order was nearly impossible. The table next to us leaned over and said they had been back 3 mornings in a row.



We left Old San Juan feeling like we had experienced a most glorious weekend away and anxious to return again. The food, people, and company were superb and we felt totally spoiled.

ps – Check out Seabiscuit’s run-down here. 







Facebook Comments