I can’t believe I’ve only been on this trip for a week. It feels like I’ve been gone for months…and like I left just yesterday, all at once.
Even with all the planning we did, it’s the unexpected turns that have led to some of our favorite moments. I’m still learning to go with the flow, and travel always seems to help with that (just one of the many reasons I love it so).
Lisbon welcomed us with pastel-colored buildings, warm, smiling faces, and leisurely mornings spent people-watching and sipping one (okay, often two) iced coffees at sunny, open-air cafés.
I’m currently traveling with my friend Martha, who is equally independent, which has been such a gift. We’re finding a rhythm that gives us plenty of time together, while still carving out space to wander and experience parts of this trip solo.
Over the coming month or so abroad, I’ll mostly be sharing weekly reflections, travel stories, and coffee shop musings. Starting with this one.
scenes from a lisbon café
It’s 12:03 p.m. in Lisbon, Portugal. I’m on hour two at Comoba, the vibiest of coffee shops—an open-air space off a semi-quiet street. Exposed brick walls peek through old plaster in shades of off-white and cream. Cool marble and round tables fill the room. Black and white tiled floors are covered in millions of tiny dots. Cinnamon buns and pastries rest on display. The whirring sound of the espresso machine blends with everything from upbeat pop music to mellow jazz.



A fan overhead sends a breeze across my neck, much needed on a day this hot. I sip an iced matcha with homemade almond milk, writing and reflecting on what I want from this time away.
on holding multiple truths
I am someone who can hold multiple truths at once.
I can want adventure and still crave a sense of stability.
I can be deeply in love and still choose this time for myself.
I can miss home and my people and still honor why I’m here.
I can wonder if the grass is always greener, and still trust it’s okay to not know.
lisbon favorites so far
A few Lisbon favorites I’m still dreaming about: Wel Well for the loveliest arrival meal—homemade everything, the kindest service, and a little NA wine shop tucked next door (Portugal’s only!). Jesus e Goes for post-massage samosas and daal, food made with real love. A solo dinner at Bar Alimentar was a definite highlight—crudo, orange wine, spring arancini, and Estelle playing overhead. For coffee and breakfast, Comoba, The Folks, and Neighbourhood all hit the spot. Cerâmicas na Linha is a must for beautifully affordable ceramics in every shade and shape, and Hoiko is a tiny handmade jewelry shop run by the sweetest woman—I left with a stone necklace I can’t wait to wear.
from city to island life
We were originally supposed to land in the Azores by 5 p.m. (a quick two-hour flight from Lisbon). Instead, our flight was delayed by 4+ hours, and we arrived closer to midnight. And after all of that, we accidentally got locked out of our Airbnb.
We considered sleeping in the rental car (it was late and we were exhausted), but instead rolled the dice on a last-minute reservation at the only open hotel nearby. It turned out to be a five-star resort & spa.
We took a chance, explained the situation, and technically got to stay for free—our original booking was refunded (with a little cash to spare). We woke up to sea views, yellow wildflowers blooming along the cliffs, salty morning air, and a hearty hotel breakfast. We spent the late morning dipping between the infinity pool and sauna.
It was the kind of magic you don’t expect, but can fully appreciate as it’s unfolding.
Over the next few days, we drove along winding roads through fields of hydrangeas in robin’s egg blue and lime green. We stocked up on olives, dark chocolate, and fresh produce, popped into a few local restaurants, and bounced between hot springs and scenic lookouts. The past 72 hours have been a total dream.

notes from são miguel
Some favorite spots on São Miguel island so far: Miradouro da Vista do Rei, where we walked through an abandoned hotel rooftop for the most cinematic view of Sete Cidades; Poça da Dona Beija, dreamy natural hot springs in Furnas (book ahead—go early or at night for the best experience); and Miradouro de São Brás, a surprise sunset lookout we stumbled on by accident. Another serendipitous mistake.
On our first night, we enjoyed a very late meal in the buzzy town center at A Tasca. We ordered patatas bravas, veggie soup, a Greek salad, and (of course) more olives.
Next up: we’re visiting a few more coastal towns in Portugal before making our way to Barcelona. I’ve also got a week or two open between Barcelona and Paris—if you have any recs, I’d love to hear them.
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I’ve been sharing real-time updates here and here, but I’ll also continue to publish new posts every Tuesday, so be on the lookout for more travel diaries like this.
Ciao for now,
Jess
So dreamy! I sent clients to the azores last year and it’s been high on my list ever since!
Why does it feel like a year?! Looks so beautiful :)