A couple of weeks ago, I went to Old San Juan, Puerto Rico. It had been a while since I flew somewhere for more than a long weekend. I didn’t have the bandwidth to do tons of research and wanted to go where I could walk around and explore easily, with options to go further afield while remaining relaxed and happy with a “home base” close by.

There aren’t too many things I like more than exploring… Wandering the nooks and crannies of a neighborhood I know little about, scoping out the local vibe, turning the corner of a colorful street and being surprised by what I see on the other side… Inhaling salty ocean breezes and feeling sunshine radiate the skin… Getting lost, feeling carefree about it and making wonderful discoveries… Jumping off a catamaran and swimming ashore to explore a little island where the only inhabitants are the local fauna… Finding shells I have never seen in such an intense pink hue…

The first thing that stands out in Old San Juan is the palette of vibrant and pastel colors that give the blue cobblestone streets a joyful, healing vibration—all the way up to the rooftop terraces, festooned with Bougainvillea. It arouses the senses and I found myself continually pausing to take it in—to burn memories, whether in my mind or on camera—to absorb the sounds and sites and smells of little corners and stretching vistas, all picturesque.

On this trip, I didn’t want to squeeze too much in and, at the very least, needed a couple of beach days to do little more than listen to waves breaking and birds calling. We decided to stay in the city to absorb more art and culture, but our beautiful hotel gave us access to a beach resort with a swim-up pool bar. Not my typical scene but colossal rum and fresh pineapple juice in hand, it was lovely. And funny. The pool bar seems to attract a menagerie of personalities.

My dear friend, Amy, was the consummate travel partner—she did have the headspace to plan, and plan she did, making sure we had a balanced mix of activities. Lucky me.

I love a good walkabout. In addition to some quintessential spots for historical reference, amazing sunsets and delicious food, we explored places off the beaten path, like a colorful dive bar Anthony Bourdain had chronicled and a well-curated vintage shop, where I bought a pair of very groovy 1970’s jeans and Amy found fabulous snake-print flare leggings to wear on stage—when she’s not planning a girlfriend getaway, she’s performing as a singer-songwriter in the Boston area.

Side note: I was happy with the shoe choices I packed, trail runners and Birkenstocks. If you plan to visit Old San Juan, all you need are good sneakers and sturdy, comfortable sandals. Please do not attempt heels on hilly cobblestone! It’s not a good look.

Speaking of packing well, I was excited to give Amy her first pair of Iconic Stretch Jeans and managed to fit them in my well-curated carry-on…

I knew she would love them, not just because they are the comfiest jeans on earth and they would look great on her (they look great on everyone), but because they are beautiful! Indeed, she loves them and wants to wear her new black floral Iconic Jeans on stage, too, as they are shimmery and will catch the light perfectly.

We wore our Iconics when visiting El Convento, a landmark monument to the Conquistador Age and one of the most historic hotels in Old San Juan. It has a timeless aura of old world charm, befitting its origins as a Carmelite convent more than 350 years ago. It was hard to resist taking photos there; the Spanish Colonial architecture and design has been so lovingly restored. The hotel has such an interesting story…

  • 1646: Construction began on the Carmelite convent, through a petition by King Phillip IV of Spain.
  • 1651: The convent was inaugurated as the Monastery of Our Lady Carmen of San José—and was situated across the street from San Juan Cathedral, the Western Hemisphere’s oldest cathedral.
  • 1903: The convent was closed by the Archbishop of San Juan.
  • 1959: Under the auspices of Operation Bootstrap, Robert Frederic Woolworth, heir to the Woolworth fortune, began converting the convent into the El Convento Hotel.
  • 1962: El Convento Hotel opened.
  • 1990s and 2000s: The property was renovated again and rechristened Hotel El Convento.

I won’t push more history but suffice to say it was a well-rounded getaway—well-needed for self care and perspective, particularly after the pandemic. Now I have the travel bug again. It’s been a while since I felt this wanderlust and I cannot wait to plan my next trip.

How about you? I want to hear about your travel plans. Do you have any bucket list destinations? Where will you go next? Where will you wander?

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