This Is What You Came For: Rolling Hills, Cypress Trees & Small Villages in the Val d’Orcia Region of Tuscany

Fortress of Radicofani – dates back to the middle ages with stunning views of the countryside

If you have been reading this newsletter for a while (thank you!), you likely know that I went on a trip to Italy last summer that was cancelled not once but twice, due to covid. It finally happened and was really a dream come true. In many ways, I am glad that it took as long as it did to go on that trip because 1) my children were older by that point and I think they enjoyed it more than they would have and 2) it took so much planning so the extra time (two years!) actually ended up being a bonus.

If you are reading this and thinking about a trip to Tuscany, consider this your one stop shop for background material before you go. In other words, all the things I wish I had known!

First, read this: A Step-by-step guide to renting a villa in Tuscany – helpful and practical tips to enhance your trip such as how to go about renting cars (request automatic vs. stick shift and two cars are better than one big one), making sure your villa has whole house air conditioning and a pool if you are going in the summer, and more. We also used drivers throughout the trip for various excursions, but found that having access to our own cars was essential.

Second, use a local travel agent – you need someone on the ground in Tuscany who can help you plan your stay and give you basics like where to park, and help set up bike rides, dinners, tours and other excursions.

Third, visit Hotel Monteverdi if you are at all close by – it is truly magical.

And fourth, use this guide below and the ones to follow as a resource for deciding which towns and villages to visit. We were there a week before heading on to part three of our adventure — Ischia — and barely scratched the surface of places to see.

Tuscany is definitely on my list of places to go back to – and I would love to visit in the Fall next time because I know it would be incredible that time of year.

RADICOFANI – I am starting with the scenic village that was close to our villa, IL CORNELLO, and while it likely isn’t on anyone’s must visit list – it was the destination of our incredible bike ride and the most memorable lunch of our trip. We used a local bike tour company, arranged by our travel agent. The tour guides met us at our villa with the bikes, got everyone fitted and settled, and off we went from our villa to the top of the village to tour the “Rocca of Radicofani”, a fortress that dates back to the dark ages before the year 1000.

“On the southern border of the beautiful Natural Park of the Val d’Orcia, rises one of the most impressive and most scenic medieval fortresses of all Italy. For centuries, the imposing Fortress of Radicofani has been the symbol of defense and control over the Via Francigena, on the border between Tuscany and Lazio. It had a considerable military importance, being a compulsory stopover for pilgrims and both for travelers.”

Biking up the mountain was a challenge but biking down was downright terrifying and thrilling all at the same time – check my Instagram Stories if you want a behind the scenes look.

NEXT UP: the other towns we visited and loved including Siena, Pienza, Sarteano and an incredible vineyard tour and private dinner in San Casciano dei Bagni.

And P.S as always, if you are enjoying my newsletter thank you for subscribing and please share with your travel loving friends and ask them to subscribe! Click here to add your email address. XO

You can see the fortress from our villa all the way on the very top right hand corner of this photo.
Tuscany is actually quite large – you can see the Val d’Orcia region on the map here in the southern section of the region.
Val d’Orcia E-bike: We had two incredible guides and they brought the bikes right to our front door.
Getting ready to head out
Off we go
This was our resting spot halfway up the ride to the fortress: “Posta Medicea is situated along the Via Francigena, an ancient pilgrimage route. Originally used as a hunting lodge, the Posta Medicea was transformed into a resting point for those traveling the Via Francigena. Travelers would stop to rest, eat, and drink from the fountain, which is still visible in front of the villa today.
The estate has hosted numerous important people, including Pope Pius VI, Pope Pius VII, Cosimo II, Leopold II, Grand Duke Ferdinand I, Marquis De Sade,  François René de Chateaubriand, and Charles Dickens. Grand Duke architect Bernardo Buontalenti designed the structure, which was completed in the late 16th century. It features a facade with double loggia and six arches.”
Ancient piazza in the quaint village where we stopped for water and ice cream.
We walked around the little piazza and took a look inside the church during our stop up to the fortress.
The views from the top of the fortress were incredible.
A dream come true for little boys – playing hide and go seek and climbing an ancient fortress.
View of the restaurant from the top of the fortress.
My parents didn’t make the trip up by bike, but the lovely owners of the rental company brought them up to meet us to tour the fortress and have lunch.
I moved too slowly to take a picture before it was devoured!
Most incredible gnocchi I have ever tasted.
Perfect dessert.
Needed a pick me up for the ride back down the mountain.

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