In this episode, I share why I don’t pack my days in Italy too tightly, and unpack what I mean when I advise clients to leave time for walking and wandering.
This episode is dedicated to Morton Kaish, who taught me how to “walk like an artist” in Italy and how even passively taking in great art and architecture can change you for the better.
You will also hear a conversation with illustrator Jenny Kroik. We talk about why places that don’t photograph well often end up being the ones that stay with you, and how sketching can help you process complex, layered moments that don’t fit neatly into “good day/bad day.”
Finally, I walk through what is planned for Jenny’s Art Retreat in May at Borgo La Pietraia, including Chef Mario’s deceptively simple food, daily gentle art prompts, visits to the Paestum temples, a buffalo farm, Amalfi’s historic paper mill, and the turquoise waters of Cilento.
I share these details as inspiration for planning your own self‑guided trip to Italy: choosing a single home base, slowing the pace of your days, leaving room for serendipity, and designing an itinerary around the kind of beauty you want to experience.
Links
Retreat details and booking: Jenny’s Art Retreat at Borgo La Pietraia (May 17–24)
Jenny Kroik’s Arthur Avenue illustrations for The New Yorker
Jenny’s website and her Substack newsletter
Pages from Jenny’s sketchbook of Paolino 848 in Trentinara, my favorite wine bar.
