Portugal was supposed to be my “slow down” trip.

Gary planned it to celebrate my 65th birthday—which was actually in March… along with his birthday and our anniversary (because March always ends up feeling like one long celebration in our house).

But April?

April felt like the right time to actually go. To celebrate it properly. To stretch it out a little. To make a whole experience out of it.

And that’s exactly what we did.

Planning the Trip

This entire trip was planned by my travel agent—and longtime friend—Lisa (@travel4fun247), who also happens to be my sorority sister.

She handled everything from start to finish and truly made the whole experience feel seamless.

From the itinerary to the transitions between cities, everything just worked—which, as you know, is not always the case when traveling.

If you’re planning a trip like this, she’s someone I absolutely trust.

Where We Stayed

We started in Lisbon at the Lisbon Wine Hotel—fun, charming, and perfectly located for walking.

In Porto, we stayed at Torel Palace Porto, which felt tucked away in the best possible way—quiet, elegant, and exactly what we didn’t even know we needed.

Lisbon Highlights

Our first two days in Lisbon were spent with our guide, Luis, who took incredible care of us and made sure we experienced the city in a way that felt both comprehensive and personal.

We explored the major sites, but also moved through the city in a way that didn’t feel rushed—which made all the difference.

By the time we had our full leisure day, we already had a sense of the city… which made it that much more enjoyable to just wander.

No real agenda.

Just walking.
Exploring.
Shopping.
Stopping when something caught our eye.

One of those days, I threw on white jeans, a light sweater, and a scarf—nothing special, but somehow it felt like the perfect outfit for wandering through Lisbon.

Those are the moments that don’t sound like much, but somehow stay with you the longest.

Day Trips from Lisbon

We also explored a few places just outside the city, and each one felt completely different.

Sintra

Felt like stepping into a storybook—lush, misty, and filled with incredible palaces.

Cascais

Relaxed, coastal, and easy in the best way.

Cabo da Roca

The westernmost point of mainland Europe—dramatic and breathtaking.

Óbidos

A charming medieval town that felt like stepping back in time.

Porto & The Douro Valley

One of my favorite parts of the trip unfolded between Porto and the Douro Valley.

While we were in Porto, we spent a half day with Lucia, who took us through the city and to Real Companhia Velha—one of the oldest wine houses in the region, owned by her husband’s family.

She took us through the Jewish Quarter, brought us to one of the most incredible city markets—where I tried sardines (which I don’t typically like)… and somehow, the way they were prepared, they were actually delicious.

She also managed to get us seated at a lovely restaurant for lunch overlooking the river—one of those moments that feels completely effortless, but you know isn’t. It was one of those experiences that felt incredibly personal… the kind where you’re not just seeing something—you’re understanding it.

The next day, we set out early with Joax, who took great care of us for a full day as we made our way through the countryside toward the Douro Valley. It was a long day—but in the best way. Winding roads, incredible views, and just enough time to take it all in without feeling rushed.

And by the time we arrived at Quinta das Carvalhas, it truly felt like a full-circle moment—having already visited Real Companhia Velha with Lucia the day before.

A vineyard that felt like stepping into history, surrounded by rolling hills and views that didn’t quite feel real.

Because in Porto, you’re seeing where the wine is aged and preserved… And in the Douro Valley, you’re seeing where it all begins.

And knowing it’s all part of the same family made it feel even more connected.

Not just tasting wine—but understanding it.

Where We Ate

Portugal just does food beautifully.

Lisbon Restaurants

• Bonjardim — unexpectedly the best chicken I’ve ever had
• Sud Lisboa — sunset dinner overlooking the Tagus River

Porto Restaurants

• Blind — a multi-course experience inside Torel Palace Porto
• Taberna dos Mercadores — small, intimate, and incredible
• Vinum — elevated, warm, and unforgettable

What I Wore (and What Actually Worked)

I packed pretty simply for this trip—white jeans, a couple of pairs of denim (cropped and longer), and a mix of easy tops and sweaters.

I also brought a few khaki separates from Aritzia that I ended up wearing constantly.

Portugal in April was colder than I expected—especially at night—which led to a Zara stop in Lisbon where I picked up a few sweaters, a suede coat, and a knit blazer.

Shoes were key—Easy Spirit sneakers, Gucci sneakers, and Frankie sandals for walking.

And yes… I brought my Inez heels—and on those nights, we Ubered.

Final Thoughts

Somewhere between Lisbon, Porto, and the Douro Valley… the wine, the walking, the long dinners…

I felt it. That shift.

Portugal reminded me that even when life is full, you can still pause in the moment.

You can stay a little longer. Walk a little slower. Say yes to one more glass.

Not a full slow-down…but a reset.

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Do you prefer to see everything when you travel… Or are you better at slowing down?

Let me know in the comments.