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Fairytale Travel Guide Helping families make travel with kids feel more doable. Trip ideas, family travel logistics, and the practical details in between.

When I’m planning a trip with my kids, I usually start with where we want to go and then figure out how to make the logi...
10/20/2026

When I’m planning a trip with my kids, I usually start with where we want to go and then figure out how to make the logistics work.

After traveling all over the United States and to 7 different countries with my two young kids, often as the only adult, I’ve gotten pretty good at knowing which details are worth thinking through ahead of time.

Things like how we’ll get from the airport to our hotel, whether we’ll need car seats, how much luggage I can realistically manage, and whether our hotel location will make our days easier.

But here’s the thing. I don’t need every part of a trip to be easy or convenient. If there’s somewhere we really want to go, I’m usually willing to figure out the more complicated parts.

I shared some of the things I consider when planning our trips in this carousel. Hopefully they’ll help you think through your next family vacation, too!

Save this for when you’re planning your next trip, and follow Kristi | Family Travel With Kids for more family travel tips, destination ideas, and practical advice from our travels.

10/19/2026

Day 3 of our 10-day Portugal trip with 3 kids under 5! 🇵🇹

Today was all about exploring Sintra, visiting Pena Palace, and making our way from Cascais to Lisbon.

We needed to change hotels anyway, so instead of booking a separate transfer, we arranged a private tour with Ó Turista () that picked us up at our resort in Cascais and dropped us off at our hotel in Lisbon at the end of the day.

This ended up being one of my favorite logistical decisions of the trip! They provided car seats for all three kids, had room for our luggage and two strollers, and gave us the flexibility to adjust our plans as we went.

A few things worth knowing about our day:

• Pena Palace with strollers: The uphill cobblestone walk from the parking area was tough, especially with a double stroller! But once we reached the palace, there were areas we could explore with the strollers, an elevator to the upper viewing area, and designated stroller parking before going inside.

• Our guide, Bruno: He was wonderful with the kids and helped us so much throughout the day. If you book with Ó Turista and can request him, I absolutely would!

• Changing plans: We originally planned to visit Quinta da Regaleira too, but everyone was exhausted after Pena Palace. We skipped it, had a long lunch at Julio’s Toca, and finished with a quick stop at Cabo da Roca, the westernmost point of mainland Europe.

We ended the day checking into the Hyatt Regency Lisbon, where we were surprised with a suite upgrade. After that long day, having the extra space was wonderful!

Sintra was absolutely worth visiting with young kids, but I’m so glad we had the flexibility of a private tour. And despite that uphill climb, I would still bring the strollers again!

Next up: Exploring Lisbon!

Follow along for the rest of our Portugal trip, or comment PORTUGAL and I’ll send you our full 10-day itinerary, including a detailed post about our experience visiting Sintra with kids.

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