Marriage, Travel, Uncategorized

Puerto Rico – Skip the Resorts to Find the Culture

Lessons Learned while Traveling – 5 Year Anniversary Edition

Typically, my husband and I choose to stay in any town’s historic center when traveling, so that we can explore what makes the place stand apart from every other village and city in the world. On this particular trip, we wanted to go the lounging-by-the-pool, drink-in-hand route, instead.

photo 2That was our first mistake.

But first a bit of back-story. Labor Day will always be preceded by weekend getaway for Jeremy and me. Our anniversary falls at the end of August, making it the perfect time to use that extra day to find a new spot on the map to explore. This year we decided we needed a chance to recharge our batteries, as it were. With only 4 days to make that happen, we jetted off to Puerto Rico since it only takes a minimal amount of points with a Southwest credit card.

Waking the next morning, it didn’t take long to realize we just aren’t long-term lounging-by-the-pool, drink-in-hand people.

photo 5 copyWe had already come to terms with the fact that we aren’t laid-back. Not in that sense, anyway. That first morning in Puerto Rico, we walked along the beach as far as we could go, swam up to the bar and sat in the water with a beachy cocktail, and then finally settled into some lounge chairs and kicked back to read while simply enjoying our time together. But after only a little while of being in the intense Caribbean heat (of which we were mostly in the shade), we had to either get another drink or risk melting right into tropical landscaping that surrounded us.

We did wind up having that second drink, then decided to get all dressed up and go into the Old City for the evening. A $25 dollar cab ride later, we were walking along cobblestone streets and reveling in what we knew we were missing.

photo 5Like every other historic town we visit, our first stop was the cathedral. A truly picturesque wedding was taking place that evening, so we weren’t able to see inside. However, right across the street was an ancient building that had at one time been the cathedral’s convent, but had since been turned into a boutique hotel.

photo 4In fact, after our mega resort, the Hotel El Convento felt like a corner of heaven. Before our trip, I had looked into this hotel – it had even made it to our short list. But without direct beach access and only Queen beds outfitting their adorable guest rooms, I passed them up. What a huge mistake! We promptly asked the front desk attendant if there was any room in the inn for the remainder of our stay, but this hotel – along with each and every other place we checked – was sold out for the weekend.

photo 4 copyBut we explored the hotel’s nooks and crannies anyway, and soon wandered throughout the city looking for the other hotels the helpful attendant had recommended. That’s when we came upon The Gallery Inn. Being familiar with this eclectic hotel due to rave reviews online and in magazines like Travel and Leisure, I knew it was highly sought after. But I didn’t expect to come face-to-face with the hotel owner, an imacumlant woman I took to be hovering in her mid-60s.

She was, in fact, in her early 80s. With silvery blonde hair and a Cockatoo perched upon her right shoulder, she graciously welcomed us into the lobby. She left as quickly as she had appeared, but the lobby attendant let us in on the fact that the sculptures which filled every crevice of the courtyard and lobby were the creation of the owner, who was quite celebrated in Puerto Rico.

photo 1 copyWe both fell in love with Old San Juan, and succumbed to the exorbitant cab fees in order to get there each day. Local unions have not only ensured that cab drivers are paid handsomely for their services, but also that the hotels and resorts will not be implementing shuttle services any time soon.

photo 1That’s not to say we didn’t sit by the pool again during our trip. On the contrary, we enjoyed a few more frozen drinks at the swim-up bar and took many more walks in the sand. The resort next door even had an amazing Airstream that sold nothing but Clicquot – so decadent! But our credit card bill can attest to what really entertained us.

I guess you could say we’re explorers at heart. But sometimes we do fall victim to the touristy cliches!


Where to Stay in Puerto Rico

Hotel El Convento

The Gallery Inn

Villa Herencia Hotel

Da House Hotel

What to Eat in Puerto Rico


El Picoteo in the Hotel El Convento

Casa Cortes Chocobar

Caficultura Coffee Shop





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