The best way to see the picturesque, cobblestoned, hill towns of Tuscany is simply by car. There are too many darling towns spread out in Tuscany and a road trip is more practical than taking public transportation. We started our journey in Naples (because we live there) but this is also a perfect itinerary for a trip from Rome to Florence.
First stop: Orvieto
Now, Orvieto isn’t technically in Tuscany. I know. Located in Umbria, it’s about a three hour drive from Naples and it’s only 90 minutes from Rome. Tuscany or not, Orvieto is a perfect stop right off the highway to stretch your legs… Not to mention lunch. Between enotecas, pizzerias and quaint restaurants, there are plenty of choices.
Second Stop: Montepulciano
After strolling around Orvieto, we continued our Tuscan road trip north to Montepulciano. We arrived just in time to catch the last few hours of sunlight and check into our hotel. E Lucevan le Stelle Wine Bar Bistro was a nice spot for dinner and regional wine (of course).
I chose Caffè Poliziano for a quick breakfast. We soaked in the view from the back balcony, finished our cappuccinos and headed out do some wine tasting…It was approaching noon and time was wastin’ ; )
Located just on the outskirts of the cobblestoned city center of Montepulciano, Gattavecchi winery is an easy walk from Caffè Poliziano. We were the first visitors of the day and the old Italian lady was just opening. She welcomed us in and signaled for us to go down the stairs to explore the underground cellar.
When we came back up she gave us a complementary tasting and even cut up some slices of cheese. She just kept speaking in Italian hoping I would get a few words out of it. The thing is though…. you don’t need to speak Italian to enjoy great wine, flavorful cheese and an authentic wine tasting experience in Tuscany.
Third Stop: Montalcino
With a few bottles to add to our collection, we headed northwest to Montalcino. The road between Montepulciano and Montalcino reminded me of Napa Valley or the California Central Coast. The entire area is sprinkled with wineries and agroturismos. We chose to stop at Cordella Winery in Montalcino and had a truly incredible experience. After a lovely afternoon of wine tasting at Cordella, we continued north to check into hotel in Siena.
Fourth Stop: Siena
After a lovely afternoon of wine tasting at Cordella, we continued north to check into Hotel Italia Siena. Hotel Italia Siena is the ideal hotel for a road trip in Tuscany because it’s near a residential area and there’s ample (FREE!) parking on the street. At the same time, you can still easily walk to the main square in Siena. They also upgraded us and had the cutest dog bed for Alfie! Of course, we brought our spoiled little ragamuffin.
I’d recommend spending a whole day in Siena….Have a relaxing drink in the Piazza del Campo, stroll up to the Fortezza Medicea for awesome views and visit the Siena Cathedral. Venchi for gelato. Pasticcerie Nannini for a sweet pastry and coffee.
If you’re lucky, you might catch a flag throwing parade! Does anyone love Under the Tuscan Sun as much as I do!? Cortona is not far from Siena if you want to live out your Under the Tuscan Sun fairytale. Wanna really go for it?….Did you know you can spend the night in Bramasole?! Villa Laura, as it’s known off the silver screen, offers weekend events full of Tuscan cooking, wine tasting, truffle hunting and olive harvesting.
We ended our Tuscan road trip Sunday and went back to Naples, but you could easily continue north for one hour to Florence. Between the Ponte Vecchio, the Uffizi Museum and legendary eateries, you can easily spend a weekend exploring all that Florence has to offer.
Happy road trippin’ my friend!