2019 has been a year of road trips for us and we have loved every moment!  Tuscany was our first official road trip of 2019.  The entire trip, we kept asking ourselves over and over why we didn’t do it sooner.  It was complete BLISS!! Of course, there was so much to see and do and we couldn’t conquer it all, so we have a second trip planned for fall. 

Because we had THE BEST TIME on this trip, I wanted to share our itinerary.  Planning our Tuscany road trip proved to be a bit more difficult than I expected, because I was set on seeing the Tuscany you see in the movies.  But since that part of Tuscany is the countryside, there isn’t as much about it on good old Google as I thought.  By the way, did you know that area is called Val d’Orcia?  I initially didn’t!

As I’m not a strict planner, I had a TON of options for things to do and see on the itinerary so we could choose at our leisure along the way.  So in the itinerary below, I’ve provided the things we did AND the things we didn’t get to do.  You know, just so you have options :). Our Tuscany itinerary hits places that are: low-key, reduced crowds, and don’t have a TON of attractions. Whether you’re planning a trip yourself, or just checking out the photos, enjoy!!

A Tuscan Road Trip | Italy

Pisa

We flew into Pisa instead of Florence (because it was cheaper).  While we were in Pisa, we took a short drive from the airport to see the Leaning Tower of Pisa.  It was BUSY and quite touristy! We spent about an hour there walking around and taking photos before we hit the road to drive south and work our way back up.

Arezzo

Along the way to our first hotel, we stopped in Arezzo.  Arezzo is known for its Renaissance art (see The Legend of the True Cross by Piero della Francesca in the Cappella Maggiore in the Basilica di San Francesco), medieval jousting (we did not see this), its famous film locations (e.g. Life is Beautiful – see Piazza Grande), and FAB antique shopping (seriously, bring a checked bag).  It was, like most of the towns we visited, quite picturesque.  It also wasn’t crowded, which was a HUGE plus for me. 

Montepulciano

We felt Montepulciano would be a great base for us in the southern Tuscan area (we were right!).  We booked one night at Villa Poggiano (10/10 would recommend). 

The town boasted vast panoramas, ancient churches, and a plethora of Renaissance buildings. We had dinner at La Bottega del Nobile and enjoyed walking around and exploring the town.  Montepulciano is know for Nobile wine (vino nobile di Montepulciano) and its underground wine cellars. It is also known as the location of the Twilight sequel New Moon (ha!), so you can expect a few more tourists than in other Val d’Orcia towns. You can tour these cellars in the town and sample all the wines!!  This was one of our favorite stops!!  Here are some wine recommendations:

• Cantine Fanetti – the “father” of nobile. 
• Villa S. Anna – an all women (production) winery

Monticchiello

We stopped in for a moment to wander one of the most beautiful medieval villages.  Not much to do here but we did wander around, buy some art, and grabbed a drink and bite to eat. From the city gate, you’ll be privy to absolutely stunning views across the valley to Pienza.

Bagno Vignoni

A small, thermal village which is unique in that its town square is a pool of hot springs!  You can’t swim in the main “square,” but you can swim in the Parco dei Mulini .  We didn’t swim, but we did visit and it was STUNNING seafoam green waters.  We spent a ton of time here just hanging out by the water. 

Winery: Podere Le Ripi

Pienza

Once the summer home of Pope Pius II, Pienza is an ideal Renaissance town.  Don’t miss the street “Via dell’Amore” aka Love Street!  The main sights include: the cathedral, Piazza Pio II, Palazzo Piccolomini, Plazzo Borgia, and Palazzo Comunale. 

Brewery: La Fonte

San Gimignano

The “Town of Fine Towers.”  The “Manhattan of the Middle Ages.”During the 14th century, every well off family in San Gimignano built a tower to show its economical power. Today, 13 towers still remain.

San Gimignano had many more tourists than any town we visited in Val d’Orcia.  Thus, we were a bit more partial to the towns down south. However, there is tons to see and do here including: the Cathedral, which is considered to be one of the most well known in all of Tuscany.  The Vernaccia di San Gimignano, a white wine produced only here, is a must try.  

For dinner: Locanda la Mandragola – Amazing quality food. Make sure you arrive early if you don’t have a reservation.

Certaldo

A small, yet extremely photographic and picturesque small town.  We randomly stopped here, but would come back.  At Palazzo Pretorio, you can tour a pretty enthralling medieval castle. Upon purchasing your ticket for the castle, you also receive entry to Boccaccio’s house.  I wasn’t super into visiting this house, but did it anyway (because free).  I was glad I did because it provided access to a tower overlooking the entire town! 

Winery: I Balzini

Volterra

A walled town known worldwide for its alabaster hand-made objects is less popular than it’s neighbor San Gimignano, but nonetheless worth the visit.  It features the oldest town hall in Tuscany (Palazzo dei Priori) and a rather unique duomo (Cathedral of Santa Maria Assunta).  The walls and gates of the city are Etruscan with many sections from the 13th century.  We also visited the Medici Fortress and walked around the Roman Amphitheater while there. 

We wandered into a tiny little wine shop that focused solely on selling small batch wines: Enoteca Scali.  They have a plethora of excellent wines on tap that you can taste, sample, or have a glass.  

Wine Tasting: Enoteca Scali

Val d’Orcia Region

Cities we wanted to visit, but didn’t make it to: Sienna, Lucca, Florence.

Maybe next time, Tuscany!