trip planning

I have a three-month sabbatical from work coming up. The company I work for (Automattic) offers it as a 5 year anniversary reward. I have never in my life had three months off to dick around, and I’m really coveting the experience.

For the first month of my time off I’ll be taking a pretty spectacular trip to both take advantage of the time off, and to celebrate my 40th birthday (something I did not really do when it happened earlier this year). I’m renting a motorcycle in Geneva, and spending a month exploring the Alps and alpine-Central Europe. When I return, I fully expect to spend most of the other two months at home eating top ramen because I’ll be BROKE from a month of hotel rooms, Swiss cheese, French food, and Italian luxuries TBD. Yolo, right?

My trip planning has been slow and taken several months, but it’s also been exciting? Every time I book a hotel room I look at the photos of these picturesque mountain towns towns like “wow, I’m going to go here? That’s insane! Maybe I will become a problem like Maria!” I’ve heavily been using Claude Code to tackle the tedious parts of planning, even making a custom site (mototourista.com, if you’d like to register to follow along) to organize my maps, hotel information, weather forecast and historical weather data, daily gear recommendations, painfully AI-generated daily ride summaries, photo dumps, trip journal, etc. The site also exports to a gpx file for my Garmin (hotel lat/long coordinates, waypoints for mountain passes on the agenda for the day), so while I’m using AI to plot out my sample maps, IRL road choices should be reliable.

I’m sure I’ll run into some kind of nonsense that I overlooked in working with AI to plan, but what good is an adventure without a little chaos? And thanks to Google maps, TripAdvisor, and the countless travel blogs out on the internet, the robot has pretty good data citations, so I’m more curious about how this will go than concerned I will run into something I can’t handle.

It’s also been a little sad to plan this solo excursion. Jordan and I talked about him taking a leave of absence to join me on any sabbatical travel, and I think about that as I book twin bed hotel rooms and share details with folks who aren’t really invested in my vacation planning. Sometimes I look at a day’s route and I think “fuck, Jordan would have quit his job to come on this trip.” It’s not a journey I wanted to confront alone, it’s one I wanted to tackle with him. We’d actually talked about doing this in Vietnam/Cambodia/Thailand, but since it’s just me, I decided that Europe felt more approachable.

This will be my longest solo travel, my longest consecutive time on a bike, and my longest trip ever. I’ve been working on enjoying my own company for the last 6 months so I’m feeling prepared for the solitude, but I am going to miss my little Pinto Bean. He’ll be with a close friend who we both trust and I know he’ll be fine, but I am gonna miss my lil’ shadow!

I think this trip will be a bit of a culmination of the work I’ve been doing on myself this year too – trusting myself, enjoying my own company, meeting my own needs, and showing myself love in the ways that matter to me. Is planning yourself an epic yolo European motorcycle/food trip and blowing through a chunk of savings self-love? Let’s find out.

Friends, please do sign up to follow along at mototourista.com if you’d like to get daily updates of my trip. I’m not sure how Insta-active I’ll be since I hate it there, but I am committing to the blog! For those who try to register and don’t get approved because I don’t know/like you IRL, never fear! The travelogue will become public a few days behind reality to maintain my illusion of privacy and safety.