I just returned from an epic 11-day trip through the country of Portugal with my best friend.

Ah, to travel.

It opens your heart, clears your head and provides a profound sense of space and a precious clarity like nothing in life can. During these past few weeks, I was able to physically, emotionally and spiritually step away from what has been an insanely magical but oh-so-overwhelming year of 2015.

As I mentioned, this year, I have manifested my dreams of traveling the world (this time, getting paid to do it) and while it’s been incredible, it’s definitely shifted everything else in my life. Namely, my marriage, my health, my friendships and family relationships and my overall sense of grounded-ness. This isn’t a positive or negative thing – it’s just the natural, inevitable order of massive life transitions and it’s a constant work in progress.

Portugal wasn’t a work trip. It was a personal trip, a decision that was born from a pact my best friend and I made to take an international trip together once a year.

Why Portugal? We both had been to Europe plenty of times and seen the usual suspects, but since neither one of us had been to Portugal, we decided to dedicate a week and a half exploring it in its entirety.

Portugal feels like a precious secret. There’s a quiet but palpable awareness amongst those that live and travel there, an unspoken knowingness of just how untapped, unpretentious and special it is.

We kicked off our trip in the colorful, San Francisco-esque capital of Lisbon, checked into our hotel and hit the town to uncover its spirited and musically progressive nightlife. After a few days of shopping independent designer boutiques and sipping rose, we hopped a train and headed north to Porto, an old-world Parisian look-alike and explored contemporary art museums, secret gardens and authentic Portuguese cafes.



From Porto, we rented a car and headed two hours due east to Portugal’s wine country, Douro Valley, perhaps one of the most aesthetically beautiful places I have ever, ever seen. Douro is a must-see if you’re headed to Portugal. Rolling hills are topped with boutique vineyards, most that double as intimate bed & breakfasts, all who specialize in Port wine. We toured vineyards, took a two-hour hike to the top of ours and caught a private sunset sailboat cruise down the Douro Valley River.



After a few days in Duoro, we jumped in our VW-automatic and drove seven hours south to the Algarve. We settled here in the small, sleepy, surf town of Sagres for four days, where we beached, biked, paddle-boarded, climbed ocean caves and cliff-jumped. The only word for it all was epic.

But what I wanted to share with you in this blog is not necessarily the details of the trip, but what I learned from it. As I said, travel disconnects you from your life and reconnects with you yourself in such a profound way and each trip leaves its own unique impact.. It’s been difficult to articulate the lessons I took away from Portugal, but per usual, I’ll try…

Just book it.

So many people have asked me – ‘How do you find time to travel?’ The truth is, I don’t. That’s why it’s critical to set your dates and book your plane ticket. Don’t worry about your itinerary: once your airfare is purchased, it all becomes real. Clicking the “purchase” button on an airline’s website has become one of the single most exhilarating parts of taking a trip.

Set an intention.

You can do this prior to jet-setting, or when you arrive – whatever calls to you. For me, it happened on our first day we set foot in Lisbon. After checking in, we went exploring in the Alfama neighborhood and stumbled into a church. As you might have already guessed, I’m a pretty spiritual chick and any house of God is a place I call home. I sat down on one of the pews, closed my eyes, took a deep breath and went within. After a few moments of quieting my mind, the word “unravel” emerged. Unravel, Jessica, it continued to say. You see, this past year, I have been going a million miles an hour. Planning three weddings, entering marriage, starting a new business, joining Corporate America and getting on 6-10 airplanes a month will have that effect on you I guess. I had been wound up so tight up until Portugal, I hadn’t been able to feel what I had been really feeling, let alone understand it. Unravel. And I did just that… (More on that in a minute.)

If you don’t gain a little weight, you did something wrong.

Girl, you’re in Europe, where the bread, cheese, prosciutto and gelato flow as easily as the wine does. Fucking eat it – and don’t feel guilty about it. Yes, travel is great for the soul, gets you out of your head and opens your heart. But let’s get real: food is one of the best and most exciting parts of traveling. The way I see it, food is a look inside a country’s soul, an opportunity for you to explore its landscape through its cuisine. And in Europe, even the simplest dish is prepared with so much attention to detail and care. Savor it. Enjoy it. Go for it. And when you get back from your trip, get right back to your routine, whatever that might be. It’s all good.

Put yourself in a wide-open space. 

Megan and I spent our first few days in Lisbon and Porto, big cities pulsing with the kinetic energy of people, trolleys and an abundance of architecture. And while Lisbon is now officially my favorite city in Europe, I also live in a big city (Chicago) and work in a big city (Dallas), where packed streets and busy roads are commonplace. Once we hit the countryside of Douro, laden with rolling hills, vineyard topped mountains and a gloriously grand river…something in me cracked wide open. On our first night there, I found myself sobbing into the arms of my friend. Like the kind of crying where you wake up the next morning and your eyes are nearly swollen shut. Yah. I hadn’t had that kind of cry in nearly a year… It was cleansing, cathartic and necessary. The half bottle of Port wine and a generous dose of compassion from my friend sure did help, but the true catalyst for the outpouring was Douro itself. Just being able to take a deep breath in fresh air on top of a mountain under a sky filled with stars was all it took. It was the single most healing moment of my trip. On your next trip, I highly recommend finding your Douro.

Just show up.

As tempting as it might be, don’t over plan it. There’s something really thrilling about arriving in an unknown place and having no idea where you’re going and what you’re about to uncover. Of course, know your route, secure your accommodations and establish the key experiences you want to incorporate into your adventure, but leave the rest up to fate. Be in the moment, let go and just say yes.



Never stop traveling with your friends.

One of my favorite quotes has always been: “It’s not where you are, but who you are with, that matters most.” Even though I got married this year, traveling with my closest friends is a non-negotiable. Megan and I are blessed. When we travel, we are totally in sync. We have the same desire for adventure, we love to be active, we never run out of things to talk about and we never stop laughing. Like all day, errr’day until it hurts and tears are in our eyes. Finding a travel buddy that matches your vibe is a gift. Hold onto them with all your heart.

jessicazweig_letslfy (1).jpeg