Off the autostrada in Puglia
Three weeks exploring the backroads of Italy's bootheel
Happy June, Traipser! Dakota here with Traipsing About, my AI-free newsletter exploring living an intentional life while reclaiming creativity as an adult. I spice things up with travel experiences, pictures, and daily drawings.


Thank you for being here. I appreciate your time and attention in this endless news cycle crush of a world.
Today I’m coming at ya from the stunning landscapes of Banff National Park. More to come there, but first, more to relate from my recent trip to Italy!
In case you missed it: Last time I wrote about being married to the CEO (and 20 years of marriage!).
Married to the CEO
Twenty years ago, Chelsea boarded a plane from Portland to Prague to meet me for a month-long first date in Europe.
We still laugh about why she did that, flew across an ocean to meet me after a series of conversations on MSN Messenger and Skype.
Highlights from a road trip through Puglia
For my three-week road trip with my mom through Puglia (Italy’s bootheel), I rented a sexy Opel Corsa rocketship car in Rome and hit the road.
After my solo time in Rome, we kicked things off visiting the two towns of my great-grandparents, then headed south. Here are some highlights from a bonding, fabulous trip together.
Taking the backroads
Sure, there are autostrada that blast through Puglia, but No Highways mode on Google Maps opens up a whole other world. Some “roads” felt more like former (or current) horse cart lanes, but that was part of the fun.




Random stops along the way (aided by Claude!)
I don’t use AI to write this newsletter, but it’s great for travel help. Pre-trip and in Italy, Anthropic’s Claude helped a LOT. Even mid-drive, I’d ask “what is interesting between these two cities?” and stop somewhere.
I’d also take photos of interesting statues, features, landscapes, ask questions, dig for more context and connection between people and places. It felt like having my own tour guide! (And yes, I probably “learned” some things that were straight-up hallucinations. But hey, I’ll never know! #cheapentertainment)




Cave dwellings in Matera
I considered avoiding Matera because it’s touristy, but I’m so glad I didn’t! There are reasons why tourists visit certain places and this was worth it. Inhabited since prehistory (7,000 B.C.! WTF!) and continuously occupied ever since, the city's residents originally lived in limestone caves.
If you visit, get up early or walk around after dinner to avoid the busy days when tour buses roll in. (This held true anywhere popular that we went).




Land of trulli
As a counterpoint, the town of Alberobello felt like a complete disaster of a tourist swarm to me. The draw of the place are trulli, cone-shaped houses with limestone shingle roofs. They’re neat...but the trulli area was a miasma of trinkets and tourists.
We beat a quick path outta there to Locorotondo, which was chill and had many trulli scattered around the countryside. It was a perfect base for four days exploring the area.




Otranto: Medieval castle and beautiful coastline
With a medieval castle overlooking the Adriatic, this was a favorite. Night walks along the waterfront, narrow city streets, and just a great vibe!




Tips for traveling with a parent (and vice versa)
My mom and I both had friends incredulously ask us, “You’re traveling for three weeks together?!” Sure, we hadn’t voyaged together before other than as a whole family, but a number of things helped make our trip a success:
We talked through what we wanted the trip to look like, but then I took the lead and planned/booked the entire thing. My mom happily went along, so we didn’t have any of the drama of people wanting to do different things.
I booked 2-room apartments for us during the trip, which allowed time apart to chill out, read, catch up on communication, and follow different sleep schedules.
I leaned into making the trip about my mom and her interests. Ceramics, madonnas in churches, street markets. Being interested in what she was into made those things interesting! She was, in turn, cool with me taking time to call Chelsea or handle stuff with our rental.
We avoided wall-to-wall days full of activities. Each afternoon, we’d take a siesta. My mom might do yoga while I’d do a workout, or she’d do art while I played piano, or we might both take a nap.

Piano break in Matera on my break-apart Piano de Voyage. Sometimes I’d split off and go for a morning hike or an evening walk after my mom had called it a night.
We were careful to keep NARG at bay. My angry alter-ego shows up when I’m hangry, so we always had energy bars or focaccia for me to munch on. In three weeks, I only snapped at my mom once while trying to find parking on an empty stomach. Hey, small wins!


These things created the conditions for lots of laughs, stories from the past, and an all-around fabulous time together. I’d totally do it again.
Traipsing About is heading even further north into the Rockies! But first, a quote for the road:
“The two risks of travel are disappointment and transformation. The fear you’ll be the same person when you go home, and the fear you won’t.”
-Kate Harris, Lands of Lost Borders (a stunning book about biking the Silk Road)
Onward,
Dakota








