The Molehill

The Molehill

travel

it's true, tuscany looks just like pleasanton california

my 4 day itinerary in the italian countryside

Viv Chen's avatar
Viv Chen
Jun 18, 2026
∙ Paid

The morning we left Rome, I got into the taxi and didn’t look back. The city was a lovely intro to Italy—and a trove for vintage shopping—but I was ready to go somewhere pastoral and quiet. A change of pace. A view of rolling hills and fluffy sheep. A pool where I could lounge and tuck into my book. I was also pretty thrilled to be reunited with the good ‘old American creature comfort that is an air-conditioned mini SUV. (Sorry not sorry).

Today’s newsletter is a recap of our 4 day itinerary through the Italian countryside:

  • where we stayed and ate

  • cool medieval towns and activities to book for day trips

  • & a bit of personal news

It’s bloated with photos that might cut off in email so read in browser for the best experience.

Paid readers get all my niche brand recs, city guides, and access to a lively 39K-person chat for $60/year, or $1.15/week.


Day 1: Yogurt gelato is a religious experience in Spoleto.

From Rome, we drove to Umbria and decided to spend one night in Spoleto. There are plenty of small medieval towns in the countryside, but here’s what made Spoleto stand out:

(1) It’s artsy. They host this huge international event every summer called Festival dei Due Mondi. We weren’t there for it, but you can tell from walking around town that it’s a major cultural/economic engine for the town. During golden hour at the cathedral plaza, we saw a group of theatre kids doing a photoshoot in costumes that I can only describe as Catholic furry-meets-Michèle Lamy.

(2) It’s extremely pedestrian friendly. Out of all the medieval towns we visited, this had the most accessible infrastructure for anyone with mobility limitations. Or anyone who just hates hiking up steep hills in the heat!!! I’m in a much better mood when I’m not huffing and puffing up crumbling stone steps. The historic center is connected by a network of free underground walkalator/escalators. It was soooo nice to ride an escalator to the top of an ancient castle. They should make Spoleto a case study in urban planning school.

tunnel to the mobilita!

We stayed at Hotel dei Duchi. It was not particularly fancy but had all the comfort and amenities we needed to feel recharged. I slept a lot better here than in Rome.

The town is compact, so you can explore all of it in one day. Also love how un-crowded it was. I found myself more prone to wandering into shops “just to browse” and look at all the tasty cured meat I couldn’t bring home bc they would get 100% get flagged by the airport USDA beagles. Didn’t want to risk it.

can all shopping baskets look like this?

This is also where we had the best gelato of our entire trip: Gelateria Crispini. Specifically, the YOGURT flavor. Omg. If you like tangier flavors or grew up drinking Yakult, you would love it! It was small shop with no line, but we later discovered that it won the top prize in the 2017 Gelato World Tour. It was so delicious I forgot to take a photo.

I felt energized enough to do a full face of ~golden hour makeup~ before dinner. Side note, can we talk about how much work it is to do makeup on vacation?! I swear it takes 2x longer. Different mirrors and counter space throw off my muscle memory, I suppose. Also sometimes my vacation brain lures me into trying something BOLD. Next thing I know I’m wetting some Q-Tips to wipe off 2cm of botched eyeliner.

Anyways, the products that did the heavy lifting were: layering two shades of blush (‘baby’ as a base and ‘flirty’ as a saturated highlight) and the trusty eadem lip balm in bissap glaze.

i loved the sound of cathedral bells at sunset.

Ended the day with dinner at Pecchiarda, a restaurant we picked solely because they had grilled chicken on the menu. I never thought I would CRAVE something as basic as grilled chicken but it sounded really good after exclusively eating cured meat carbonaras in Rome. Also, when you live in the Bay Area, you get reverse sticker shock abroad—this 8 euro natural wine would easily cost $40 at a place like Verjus…

I couldn’t get over how the eggplant parmigiana looked like a butchered Hungry Caterpillar:


Day 2: In which I went to a remote medieval town and still saw a fashion hoe in Margiela tabis.

Left Spoleto in the morning and made a stop in Orvieto (another medieval town) on the way to Montepulciano where our farmstay was. You know what’s so crazy?

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2026 Viv · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture