We did it. We packed up our life (plus diapers, snacks, board books, and loveys) and boarded a plane for Portugal with our 1-year-old daughter and 3-year-old son in tow. Ambitious? Absolutely. But also… unforgettable.

Let me start at the beginning—because this trip didn’t exactly roll out like a Pinterest-perfect vacation but was also perfect in every way.

Day 1: Planes, Delays & Playground Therapy

Our journey kicked off with a delayed overnight flight from Denver to Munich. Overnight flights with two young kids are a bit like parenting on hard mode—you’re crossing time zones while navigating toddler sleep cycles, airplane meals, and the occasional in-flight meltdown. (Ours included one from the baby… and maybe a mini one from me.) I will say that we flew Lufthansa and they are one of the best airlines in my opinion. Overall I think they have some of the best planes, the food is pretty good, and the flight attendants are always sweet.

After a quick layover in Munich where we had just enough time to jog between terminals, we finally landed in Lisbon in the early afternoon. We were running on fumes, goldfish crackers, and the dream of an early hotel check-in. And then came the real kicker: my suitcase and the baby’s bag didn’t make it.

No clothes. No pajamas. No baby formula, diapers, or pacifiers. Just happy with the fact that we made it to Europe.

We headed to our hotel—Lisbon Marriott—which thankfully had a great family-friendly atmosphere and super helpful staff who commiserated with our lost luggage saga. After settling in and taking a few deep breaths, we decided not to let the missing bags ruin our momentum. We freshened up as best we could and headed into the city for a much-needed reset.

Lisbon immediately charmed us. Cobblestone streets, vibrant tile walls, and the warm late afternoon sun made it hard to stay stressed. Our first stop? Shopping. We found a few quick essentials (and a cute outfit or two I definitely didn’t need but now cherish as Portugal souvenirs), then made our way to Time Out Market for dinner.

If you’ve never been to Time Out Market, imagine a giant food hall filled with gourmet local eats, buzzing with energy and the smells of seafood, grilled meats, fresh pastries, and espresso. We grabbed a table, ordered a little of everything, and let the kids pick at all the bites we chose. There’s something magical about a dinner where no one expects your toddler to sit still—just eat, wander, and experience.

On the way back, we stumbled upon a small neighborhood playground, tucked between tiled buildings. Our kids lit up. They climbed, giggled, and ran around with local children like they weren’t totally jet lagged and running on half a nap. It was one of those spontaneous, joy-filled moments that reminded us why we chose to travel in the first place.

By the time we returned to the hotel, both kids were sound asleep in the stroller, completely worn out from the day's activities. We carefully carried them up to the room, took turns showering to freshen up, and finally jumped into bed, grateful for a moment of rest.

Day 2: Castle Views & Finally… Clean Clothes

Morning came early—thank you, toddler time zone confusion—and so did the blessed news: our bags had arrived! I’ve never been so thrilled to see a suitcase. Clean clothes, baby wipes, our sleep sack, and snacks from home had never looked so beautiful.

We set off for the day feeling like new people. Our destination: Castelo de São Jorge, one of Lisbon’s iconic landmarks. Getting there involved winding uphill streets and pushing a stroller over some very fun cobblestones, but the views were worth it. The castle sits high above the city and offers sweeping views of Lisbon’s red rooftops and the sparkling river. Our 3-year-old was fascinated by the old stone walls and canons, and our baby loved the peacocks wandering the grounds like they owned the place.

After the castle, we made our way back down to the city center, stopping for gelato and letting the kids stretch their legs. One of the best parts of Lisbon? The abundance of pedestrian areas and outdoor cafés where families are more than welcome to linger.

We found a charming spot for a late lunch and took our time. No rushing, no strict schedule—just soaking in the city and watching trams rattle past. With little kids, sometimes the best travel days are the slowest ones.

Back at the hotel in the early afternoon, we made the unanimous decision that it was definitely pool time. The Lisbon Marriott features a lush and inviting outdoor pool area that truly felt like a little oasis nestled right in the middle of the bustling city. Dinner that evening was delightfully simple—room service delivered to the patio of our hotel room, where we enjoyed the beautiful colors of the sunset as the kids wound down, played with toys from home and read our favorite bedtime books.

Day 3: Road Trippin’ to the Algarve

After breakfast at the Marriott (a buffet complete with fresh pastries, fruit, and strong coffee—bless), we packed up our car and began the drive to the Algarve. It was our first big transition of the trip, and we weren’t sure how the kids would handle a few hours on the road.

Surprisingly? They were rockstars. With a solid nap rotation, plenty of snacks, and a playlist of toddler tunes and gentle background music, we wound our way through Portugal’s countryside feeling like road trip pros.

As the city gave way to rolling hills and coastal cliffs, I felt that familiar family travel rhythm start to settle in. We had survived the jet lag, the lost bags, the 3 a.m. wakeups—and we were just getting started.

Reflections from the First Few Days:

Traveling with toddlers is chaotic—but rewarding. You’ll question your sanity (often), but the memories are so worth it.
Always pack essentials in your carry-on. I mean it. Pajamas, diapers, snacks, and a toothbrush will save your soul.
Portugal is incredibly welcoming to families. Whether it’s a playground in the city center or castle ruins that double as a jungle gym, there’s no shortage of kid-friendly magic.
Slow travel wins with little ones. Not every hour has to be scheduled. Leave room for naps, snacks, and the occasional meltdown.

We’re off to the Algarve next, where we’re trading cobblestone streets for sandy beaches. Stay tuned for sunshine, sleepy stroller naps, and our attempts to eat seafood with a baby on one hip.