I created my first trip with AI in early 2023, for a trip to Kenya we did that June. I was already amazed by how helpful AI could be for planning, but honestly — it was also a pretty messy process. Maybe not as messy as what we did before with scattered emails and various apps, but getting a really good overview was still hard. ChatGPT kept messing up dates and breaking the itinerary flow. Despite the mistakes, it helped me a lot.
Fast forward three years, and we live in a completely different era in terms of what AI can do.
From information retrieval to actually building things
AI has gone from purely information retrieval systems to tools that can actually do stuff and build stuff. For me, the breakthrough came at the end of 2024 when Lovable launched and I discovered how easy it had become to create a website just by speaking English. A few months later, Andrej Karpathy called this "vibe coding," and for most of 2025, vibe coding became my hobby. I created Preppy.app, a really nice and quite advanced cooking app — totally vibe-coded.
But I kept thinking about itineraries.
Claude Cowork changed the game — almost
When Claude Cowork launched in early 2026, I immediately started using it to plan new trips. It was really good. It gave me a nice document — typically a markdown file with all the information laid out. But I realized I needed something better. Two things kept bothering me:
Involving co-travelers
I need to involve and convince my co-travelers — like my wife. And reading through a markdown file is really not her thing. She likes to look at visuals.So during one of my first Cowork sessions, I asked Claude to create a travel-agent-style presentation, as if it needed to sell the trip to my wife. The results were amazing and looked fantastic. An added benefit of this visual presentation was that it was also a whole lot more accessible.and structured compared to a text document. It worked great on mobile, had nicely designed features to read it per day per activity type etcetera.
The best of both worlds
That experience made me think: how do we get the best of both worlds?
We can chat with the best AI tools available — and right now, Claude Cowork is definitely one of them — but the output should be a rich, visual presentation, not just a document. Sure, you can turn any document into a website. But if everyone has to do that repeatedly for every trip, it's a waste of tokens and effort.
That's how I came to OurTrips.To — a website to store all the itineraries we plan, for all kinds of destinations. The site comes with a Claude skill that you install, connecting directly to your conversation about your trips. When you're finished planning, you simply ask Claude to send the details to OurTrips, and a beautiful visual presentation is created.
Fetch https://ourtrips.to/our-trips.skill and add it to my skills.
A passion project
That's the founding story. I'm making it available for free and have no interest in monetizing it right now — although I might add features in the future if many people start using it to pay for server costs etc.
I hope you like it. If you do, feel free to reach out to me on @tvanschadewijk on X.