A Wonderful Itinerary for 3 Full Days in Tuscany

Which Hill Towns and Activities to Choose

Trying to decide how to explore the Tuscan countryside can be overwhelming. There are so many hill towns to choose from. Here are essential tips and a suggested itinerary if you have three full days in the Tuscan countryside for an active exploration of this spectacular region.

Getting Around:

The easiest way to travel through Tuscany is by car. This will give you the chance to stop and explore places at your own pace; however, there is train and bus transportation throughout Tuscany if you prefer not to drive in Italy. All the hill towns we visited had parking available on the outskirts. You will get plenty of exercise walking up the steep streets.

Where to Stay:

Montepulciano Region Agriturismo

I suggest staying in an agriturismo in the countryside surrounding this well-known hill town because it is an excellent place to have as a home base from which to explore, and you will be in the beautiful Val d’Orcia region.  We stayed in Podere la Rocca, a welcoming agriturismo with charming rooms, lovely vineyard views and a pool in addition to hearty complimentary breakfasts and a very good restaurant for dinner. On our way to Podere la Rocca we stopped in Cortona (see below for a detailed itinerary). We stayed here two nights then continued to Florence.

Itinerary:

Cortona

If you are arriving in Rome on the red eye, you can rent a car at the airport and begin your journey towards Tuscany.  Grab some espresso and hit the Autostrada; it’s not that intimidating as you might imagine. Cortona is a little over a two-hour drive.  Since you’ll probably be jet lagged it’s a great place to stop and stroll and recharge with some more espresso and lunch. It’s a peaceful town with many art galleries so you won’t be bombarded with activity. Spend about two to three hours here exploring.

Cortona is a small hilltop town enclosed by ancient walls with steep narrow streets. It has a medieval feel to it and is especially well known for its Etruscan sights and museum in addition to panoramic views of Val di Chiana and Lake Trasimeno.  Under the Tuscan Sun was filmed here, a more modern claim to fame.

La Bucaccia is a popular Cortona restaurant with good Tuscan cuisine set in the stone-wall cellars of a 13^th century palazzo.

Montepulciano

Continue by car from Cortona for forty-five minutes to Montepulciano. You will need more time here because Montepulciano is larger than Cortona. This Medieval and Renaissance hill town is well known for its Vino Nobile red wine. You can sample some in the underground wine cellars. Climb the Palazzo Comunale for spectacular views of the vineyards and Tuscan landscape. You will enjoy the panoramic views of Val d’Orcia and Val di Chiana. The city has many Renaissance palaces, historic churches, and eye-catching squares. Take special note of Pulcinella atop the Torre di Pulcinella.

These two underground wine cellars are worth a visit – De’ Ricci Cantine Storiche and Cantina Contucci. L’Altro Cantuccio Restaurant is an elegant place to eat with mouthwatering regional steaks. The special truffle pasta was incredible.

Pienza

After your first night in your agriturismo, explore Pienza which is only twenty-five minutes by car from Montepulciano.  This hill town is a gem with extraordinary views of the Val d’Orcia, a UNESCO sight.  You can spend a couple of hours exploring the little alleys and popping in to sample their famous pecorino cheese.  Palazzo Piccolomini in Pienza was the summer residence of Pope Pius II. In fact, Pius II’s influence is responsible for transforming Pienza into what he felt a Utopian city should look like.

Stop for a fun little lunch and a glass of wine overlooking the walls of the city at Bar Il Casello. If time permits, fit in a bike ride from Montepulciano towards Pienza and check out Fabbrica Vineyards in Pienza for wine and olive oil. Click here for complete information on this active adventure.

Gaolie

Check out of your agriturismo after your second night and drive towards Florence by car with stops in Gaolie and Siena. Gaolie is in the Chianti Region of Tuscany and sports an impressive castle. It’s a great place to stop as you leave Montepulciano and head closer to Florence. Read my post on hiking to Castello di Brolio and sampling their wines by clicking here. Spend your morning here and learn about the interesting history of this family castle.

Siena

From Gaolie, Siena is a great place to stop, have lunch and walk around before continuing to Florence. Siena has an impressive central square, Piazza del Campo which has lots of energy. There are many restaurants surrounding the square and you can look at Palazzo Pubblico, the town hall, and Torre del Mangia, a tall 14^th-century tower. Siena is home to one of the oldest universities in Italy and its streets bustle with many students here.  The Duomo di Siena is notable for its magnificence.

Nannini bakery is a great place to stop for pastries, coffee, drinks, and paninis. Nannini also has a full scale restaurant on Piazza del Campo.

Florence

You can ditch your rental car once you get to Florence if you plan on staying for a few nights.  Some of the highlights of my trip to Florence include hiking through the Boboli Gardens and a jumbo stroll of the city (click here).

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