Using AI to Plan an Extended Road Trip

I've been planning a two-month solo van trip to Alaska for most of this year. When you start trying to coordinate something this big, two months on the road, international border crossings, ferry reservations, Maria flying in for two weeks, mushroom festival dates you absolutely cannot miss, campsite reservations inside national parks, fishing licenses across three jurisdictions, and a return route through the Inside Passage, the planning stops being fun pretty fast and starts feeling like a project management job.

That's when I decided to try something different. I've been in IT for a long time and I'm not afraid of new tools, so I started working through the whole trip with Claude CoWork, Anthropic's AI assistant, to see how far we could get together.

The short answer: further than I expected.

What We Actually Built

Over several sessions, the planning turned into a full suite of documents I'll actually use on the road. The itinerary went through seven versions as dates shifted, friends' schedules changed, and I decided I wanted more time at certain places (two nights at Liard Hot Springs instead of one, for instance, and a full slow day in the South Okanagan instead of just blowing past the border). Each version was a real Word document, properly formatted, with a phase-by-phase breakdown of the entire route from Bend through British Columbia, the Yukon, Interior Alaska, the Kenai Peninsula, and home via Haines on the Alaska Marine Highway.

The interactive maps ended up being one of my favorite outputs. Every phase of the trip has its own clickable map tab — click any waypoint and you get the full notes for that stop. Campsite reservations, crabbing spots, shore fishing locations, mushroom festival registration deadlines, hiking options, crab ring tips, Tracy's King Crab Shack in Juneau. It's all there on the map, not buried in a document somewhere.

We also built a full Google Calendar that syncs all the major milestones, a public-facing trip page so my clients and coverage team can reach me in an emergency, a van packing database with 213 items organized by category with tracking columns I'll fill in when I actually load the van next week, and a pre-trip task checklist with deadlines.

Where the AI Really Helped

The place I noticed the most value wasn't the document formatting — it was the flexibility. When Maria's work schedule changed and we had to rethink which ferry she could realistically take home, we rebuilt that whole section in minutes, with the calendar updated, the maps adjusted, and the itinerary revised to match. When I decided I wanted to add a two-night stay at Liard Hot Springs, every downstream date and day number updated across all the documents.

It also just knew things I didn't think to ask about. It flagged that Girdwood Fungus Fair foray spots are capped at 15 people and registration opens at a specific time on August 15 — that's the kind of detail that would have cost me a missed registration if I hadn't had it surface at the right moment. It reminded me about the Sign Post Forest in Watson Lake and that I need to bring a Bend, OR sign. It knew that Allison Point outside Valdez is one of the best accessible shore salmon spots in Alaska. It told me that Tracy's King Crab Shack in Juneau during my ferry layover is a legitimate world-class meal, not a tourist trap.

What It Actually Felt Like

It felt like planning with a very well-read travel partner who never got tired of revising things. I'd say "actually I want to spend more time in the South Okanagan" and instead of sighing, it would just update the itinerary, renumber the days, adjust the drive distances, and ask if I wanted to add hiking options for the extra day. That kind of iterative flexibility is hard to get from a guidebook or even from a very patient human friend.

The Biggest Problem

If I'm being completely honest, the hardest part of this whole process was stopping. Brainstorming with an AI that actually knows what it's talking about is genuinely entertaining, and every answer opened up three more interesting directions to explore. Crabbing came up and suddenly I had a full breakdown of Dungeness seasons, castable snare traps versus ring nets, which spots on my specific route have sandy bottoms versus rocky, and restaurant recommendations for fresh king crab in Juneau. Bear spray turned into a 20-minute deep dive on chest holsters and delivery patterns and blowback in crosswinds. I spent a lot more time reading and considering options than I expected, not because the information was hard to get to, but because it was so easy and interesting to keep going. If you're a person who likes to know things, that's a real time sink. A fun one, but a real one.

Is everything perfect? No. I'll still make changes on the fly once I'm out there, and that's by design. The whole plan is built around having enough structure to feel prepared without being so rigid that I can't stay an extra day somewhere special.

But when I leave Bend on July 20 and point the Transit north on Highway 97, I'll have a better-organized plan than I've ever had for any trip I've taken. And I'll know exactly where to drop a crab ring in Homer.