Planning Our Trip to the Oregon Coast and High Desert
Tidepools, Puffins and Cheese, OH MY!
How I Used AI to Plan Our Oregon Coast Family Road Trip (And What I Had to Fix)
Planning an 11-night road trip with a 4 and 7 year old from Texas to Oregon felt overwhelming. Four stops, flights, rental cars, lodging, activities, restaurants, packing lists for four people — I didn't know where to start.
So I started with AI.
I gave Claude our family details — two kids, ages 4 and 7, we wanted outdoor adventures but nothing too intense, we love good food, and we needed a relaxed pace. Within minutes I had destination suggestions, activity ideas, and a rough itinerary I never would have put together on my own. It suggested places like Thor's Well at Cape Perpetua, the Darlingtonia Botanical Wayside (free pitcher plant preserve the kids absolutely loved), Lava River Cave in Bend, and Smith Rock State Park — all things I'd never have found on my own without hours of research.
Where AI really shined: suggestions. It knew the Oregon Coast and High Desert in a way that would have taken me weeks to research independently. It also helped me build a complete packing list for four people, research kid-friendly restaurants along our route, and create a day-by-day itinerary document I could share with family.
Where I had to push back: pace. Left to its own devices, AI wanted us moving faster than made sense with young kids. It kept suggesting we add stops and cover more ground. I had to specifically tell it we wanted to stay in each location for at least 3 nights — we didn't want to pack up every day — and that we needed buffer time for just being at the beach. Once I gave it those parameters, it adjusted and the itinerary became something we could actually enjoy rather than just survive.
The result: 12 days covering Cannon Beach, Florence, Bend, and Portland. Haystack Rock at low tide with puffin interpreters. Dune buggy tours. Sea Lion Caves. Powell's Books in the rain. The best Nepalese food I've ever had at a taphouse in Sisters, Oregon.
It was the best family trip we've ever taken. And AI got us there faster than I could have on my own — as long as I stayed in the driver's seat.
Practical tip if you want to try this: Be specific about your kids' ages, your pace preference, and how many nights you want to stay in each place. The more parameters you give it, the better the output.
