Hi friends! Welcome to Salted Cobblestone, to my first real post, and to a story I didn't quite see coming. I'm Sarah: 42, mom of three, twenty years in health tech, most recently leading a product team of 85 humans I genuinely adore. Last month, I made the hardest, clearest decision of my life and stepped away from my role. My life has never been busier or more complex. I recently lost my mom and I need to stop, breathe, and figure out what I actually want next.
And before I go any further, this. To my team — past and present — if you happen to read this, please know: you mean the world to me. Getting to build that team, and to watch each of you grow into the kind of leaders you are now, has been one of the great honors of my career. You are extraordinary, every single one of you. I'm cheering for you, loudly, forever with DAY ONE energy! 💜
And so: Salted Cobblestone. Travel has always been the thing that makes me feel most like myself, and I wanted to build something small and beautiful around it. This was my very first trip as a travel advisor. Totally normal first trip. 😅
So — I just got back from a few days in San Juan and I have a lot to say. Some of it is about the hotel (opinions: many) and the food (go to Kaffe Haus immediately, no questions). But some of it is about why this trip hit differently than I expected — so stay with me for a second before we get to the restaurant recs.
I traveled with my colleague Nikki. Technically I'm her boss's boss, which on paper sounds like a recipe for a very awkward trip. In reality: we are two women in our 40s, both mothers, both daughters of complicated parents, both trying to figure out how to hold the career and the motherhood and the ambition and the guilt and the love all at the same time. We looked at each other and said — why not? So we went.
It was one of the best decisions. We talked for four straight days — about our childhoods, the parts we don't usually say out loud. About what we're proudest of in our kids. About what it actually feels like to try to be the kind of mom you want to be while also having the career you've worked hard for. We cried a little. We laughed a lot. We also watched Dateline in the hotel room, which I will never apologize for and which is truly one of the great pleasures of any hotel stay.
Here's what I'll say about grief, because I want to be honest: it follows you. Even to paradise. Even when you're having a good time, there's this quiet hum underneath that you can't turn off. I'd been running since my mom died — managing the kids, wrapping up work, just getting through days. This was the first time I'd slowed down enough to actually feel it. That was both necessary and a little brutal. On the last night I had a dream about her — first one since she died. She was sitting right across from me, but there was a pane of glass between us. I could see her. I couldn't reach her. I woke up at 4am feeling wrecked and also weirdly relieved. I think that's what the beginning of healing looks like. It doesn't feel like healing yet. It just feels like less numbness.
She would have loved Puerto Rico, by the way. She was notoriously nervous about trying anything she deemed "exotic" — until someone (usually me) forced her, at which point she almost always decided she absolutely loved it. She texted me on her birthday this year thanking me again for "introducing her" to pad thai. Her favorite food. I would give anything to have taken her here and watched her nervously try mofongo and then ask for seconds. I'm glad I went anyway.
Okay. The hotel — I have thoughts.
Why Puerto Rico
Is More Accessible Than You Think
If you've been on the fence about Puerto Rico, let me remove a few mental barriers:
Hyatt Grand Reserve:
Beautiful — But Read This First
I booked on points — 20,000 Hyatt points per night, which is one of the best deals in the hotel points world right now (though slowly changing, so if you're sitting on Hyatt points: use them). Walking in, the space is open and airy in that exactly-right Caribbean way.
Lush tropical grounds, lizards absolutely everywhere — which Nikki went so far out of her way to avoid that she described it as "respecting their space." The fear in her eyes told a different story. I found this deeply funny every single time.
Three pools, a swim-up bar with surprisingly inventive, tasty — and very affordable for a resort — cocktails. They have all the classics (who doesn't live for a piña colada on vacation?) but also some fun new takes on the traditional pool drink. Plus a spa that delivers on massages (less so on facials).
Check-in was flawless — our room ready at early-noon! I hear it gets quite crowded, but when we arrived it was pretty quiet. The staff was warm and kind. One afternoon we returned to our freshly cleaned room to find a complimentary bottle of prosecco and a fruit plate waiting! It was a lovely gesture. We took it to the beach and watched the sunset on our second evening. That part was perfect.
The concierge does not exist in any functional sense. I asked for help getting a car and some off-property restaurant recommendations and was passed between three different people and got no useful answers. You will need to do your research and book everything before you arrive (or better yet, ask me to book for you!)
The beach was serviceable, but could benefit from a little more love — more chairs, cleaner sand, better service. My honest take: great for couples wanting quiet, good pools, and access to El Yunque rainforest. Not the right choice if you need concierge support, beach club energy, or are traveling with kids who need entertainment.
The Food:
Let Me Save You Some Time
Best meal of the trip, and I am not being dramatic when I say this was one of the best empanadas I have ever eaten in my entire life. The croquettes: extraordinary. The Cuban sandwich: phenomenal. It's buzzy, warm, welcoming, totally unpretentious — a 4.5 on Google and every star is earned. Take everyone you love here.
That room. All curves and soft light, like being inside a very beautiful clam. The food was excellent (no surprise there — it's a Michael White restaurant!): incredible Mediterranean spreads, superb crudo, a lobster risotto worth the flight. We were sadly a few minutes late for our reservation and we lost our spot! Luckily, we were able to grab a spot at the bar and they serve the full menu there!
Old San Juan:
It's As Good As Everyone Says
Yes, everyone says Old San Juan is amazing. They're right. The cobblestones, the painted buildings, the way the city tumbles downhill toward the ocean — it delivers. Give yourself a full unhurried day.
Señor Paleta for artisan popsicles is non-negotiable. Get one, find a spot on the street, sit in the sun, and just be there for a minute.
And then there's the list I didn't quite make it to this trip — which means I'm already half-planning the next one. Café Cuatro Sombras for coffee, roasted in-house with a beautiful courtyard. El Morro for sweeping Atlantic views from the old fort walls. La Factoría before 5pm for hidden rooms and excellent cocktails. And a special shoutout to Chef José Sánchez at Marcella — we heard incredible things and absolutely will not miss it next time.
Two women in their 40s, each other's unlikely travel companions, watching Dateline in a hotel room in Puerto Rico after a day of cobblestones and very good wine. Sometimes that's exactly what healing looks like.
Puerto Rico is wildly underrated — real history, real food, real culture, and logistically one of the easiest Caribbean trips you can take from the US. The Hyatt Grand Reserve is a strong choice on points for couples wanting a quiet beautiful base, as long as you know the location and plan around it. For families, beach clubs, or a more central home base — look at the Fairmont El San Juan or El Conquistador. I've now seen both sides and can give you an honest comparison. Just ask.
I came home with a little more peace than I left with. Not fixed. Not done. But something shifted — you only notice it afterward, when you realize the weight feels slightly different than it did before.
My mom would have nervously tried the mofongo because I made her, and then eaten the whole plate and texted me about it for years. I'm glad I went. I'm glad I slowed down long enough to feel all of it.
What's next? A trip out west to do some epic hikes with my nearly 11-year-old son. We'll both be doing a review — stay tuned. 🥾
Salted Cobblestone is officially open. If you want to go to Puerto Rico — or anywhere else — I'd love to help you plan it. 🧂🪨
— Sarah