A Two Day Girlfriend's Adventure in Puerto Rico — Fine Art Film Travel Photography

It was probably last summer when my best friend started strongly suggesting we get a trip on the books for my 40th Birthday in February. “We can’t just let it come and go without doing anything. You’re turning 40!” she’d say. We cleared our schedules for a long weekend adventure and then… I just couldn’t commit. Where to go? Who could come? Would I want to be away from my hubby and family on my actual 40th bday? I drug my feet and it wasn’t until the beginning of my birth month (and after my miscarriage) before I could get serious about getting something booked. I dreamed of lounging by a pool, a turquoise water view and some lovely R&R with yummy food. Florida was filled to the brim this time of year and all our favorite resorts were either booked or only available at an exorbitant price. Then we noticed that flights to Puerto Rico from Tampa were crazy affordable and resorts weren’t nearly as expensive. We could fly to PR and stay a few nights at a lovely resort for less than booking a place in Florida. And it checked all of my boxes. Plus we ended up doing a mid week trip that got us back on the Saturday of my actual birthday. Which mean’t I could celebrate the day with a bday dinner with the hubs and my family at our favorite hometown restaurant. We were in!

Two days and three nights in PR wasn’t nearly enough but it was what we had so we made our itinerary and adventure selections and factored in some good R&R by turquoise waters too. Below you’ll find a peek into the adventure through a fine art film photographers eyes. But first I’ll give you a quick rundown of our itinerary:

+ Wednesday night flight from Tampa, FL to San Juan Puerto Rico
+ An impromptu San Juan tour with Alberto, my sweet grad school friend and PR native who picked us up from the airport
+ Checked into our home base for the trip, The Condado Vanderbilt, a.k.a. heaven
+ Late night stroll and dinner at Cocina Abierta, a farm to table dream
+ Thursday: breakfast and coffee at ChocoBar in Old San Juan
+ A slow morning strolling and shopping through Old San Juan
+ Afternoon relaxing and snacking poolside at The Condado Vanderbilt
+ Dinner Eter Rooftop Lounge (although an even storm meant we couldn’t sit rooftop. Still yummy food and we finally tried Mofungo.)
+ Friday: early morning breakfast and coffee “to go” at Ola oceanside at the hotel
+ Morning pick up for our Catamaran Snorkel and Picnic Cruise to Icacos Island (insert the perfect turquoise waters here)
+ More afternoon poolside relaxing at The Condado
+ Bday celebration dinner at Oceano by the sea. More yum.
+ Saturday: last morning relaxing pool and oceanside with a beach stroll.
+ Packed up and caught an early afternoon flight back to Tampa
(+ Bonus: Saturday night Bday Dinner with Family and Friends at my fav hometown spot, Faded Bistro in Sebring, FL)

If I go back (and I truly hope I do) I’d definitely want to factor in some time to get to the El Yunque National Rainforest and some other spots around PR and the surrounding islands. You just would need a bit more than two days for all that. But for now I have my heart full of love for this island paradise with so much character and charm and my head full of so many gorgeous vistas and vignettes captured on film. Check it all out below…

xoxo, Caroline


We flew out of Tampa on a Wednesday night and landed in a sparkling San Juan, PR just after a rain storm in the dark. My sweet old grad school friend and Puerto Rico native, Alberto, scooped us up from the airport, gave us a quick and charming San Juan tour in the dark and left us with some great food recommendations, one of which we tried out right away. We dropped our bags off at our top floor, birds eye view room in our spectacular oceanfront resort, The Condado Vanderbilt, and walked down to our first yummy food stop, Cocina Abierta. Delish.

The next morning we woke up without alarms and took in the beauty of our lovely hotel. The Condado Vanderbilt was a gem through and through.

We spent Thursday morning and into the afternoon snacking, shopping and strolling the cobblestone streets of the charming, port side Old San Juan.

After relaxing poolside Thursday afternoon and a San Juan dinner at Eter Rooftop Lounge we woke up on Friday early, grabbed a quick breakfast oceanside at Ola at the hotel and were scooped up for our Catamaran Snorkeling and Picnic tour to Icacos Island. The tour was perfect with breathtaking turquoise water views, island strolls, snorkeling adventures and making lots of new friends along the way.

We finished the trip with more poolside relaxing, lots of life-giving conversations with the bestie and a lovely dinner at Oceana by the sea before flying out Saturday early afternoon. What a wonderful bday treat! And lastly here’s a little iPhone peek into the adventure (complete with a selfie here and there).

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