The Very Best 4 Day Tuscany Itinerary

Choose your Home Base for your Four Days in Tuscany

Picking the right home base can make or break your Tuscany itinerary.

For me, Montepulciano or Arezzo stand out as ideal spots. Each is central enough to explore both the Val d’Orcia’s postcard-perfect landscapes and the Chianti region’s famous vineyards.

Montepulciano is a hilltop gem with excellent wineries and stunning views, making it a top reason to visit. While Arezzo feels less touristy, with an interesting history and vibrant local culture are a couple of reasons why it’s worth visiting.

Staying in one of these towns means you will spend less time on the road and more time enjoying this itinerary I will now share.

A 4 Day Tuscany Itinerary

Day 1: Pienza and Montepulciano

Dedicate your first day to the Val d’Orcia region. Start in Pienza, known as the “ideal Renaissance town.” It’s small but packed with charm, and the Pecorino cheese shops are impossible to resist. Be sure to walk to the edge of town for sweeping views of the Val d’Orcia landscape. This is one of Italy’s UNESCO-listed sites, and not to be missed.

For a memorable lunch halfway between Pienza and Montepulciano, I highly recommend Podere Il Casale. I enjoyed a delicious lunch at this organic farm and farm-to-table restaurant with a stunning backdrop of the Val d’Orcia.

Drive to Montepulciano, where you can tour historic wine cellars and sip Vino Nobile di Montepulciano. This hilltop town is a pleasure to explore and it’s much larger than Pienza including its piazza.

Day 2: Cortona and Arezzo

For your second day, begin your day in Cortona, the hilltop town made famous by Under the Tuscan Sun. Stroll its cobblestone streets, visit the Museo Diocesano, and take in the views of Lake Trasimeno.

For an exceptional lunch in Cortona, I recommend the cozy La Bucaccia – Da Romano, for its authentic Tuscan dishes and handmade pasta.

Then, head to Arezzo, about 45 minutes away. I loved the local vibe here—it’s less touristy but full of history. Spend your afternoon exploring its highlights like the Basilica of San Francesco and its famous frescoes, then enjoy dinner in the main piazza lined with locals.

Day 3: Siena and Monteriggioni

Dedicate day three to Siena, where the medieval streets feel like a step back in time.

Spend your morning exploring the stunning Piazza del Campo and climbing Torre del Mangia for panoramic views. Don’t miss the Siena Cathedral—it’s one of the most intricate I’ve ever seen and the reason why this city is on the UNESCO site list for Italy.

Late afternoon, drive to Monteriggioni, a charming fortified village just 30 minutes away. It’s small enough to wander through in an hour, and the views of the surrounding countryside are worth it.

However, if you’re looking for a swap, consider visiting San Gimignano instead of Monteriggioni. Known as the “Town of Fine Towers,” San Gimignano is more famous and visited due to its stunning medieval skyline and intact city walls.

Day 4: Montalcino and the Chianti Region

End your trip with a visit to Montalcino, home to the famous Brunello wine.

Take a tour of a winery or simply enjoy a glass in the town square. Make time to drive through the Chianti wine region on your way back. Stop at a local vineyard to sample Chianti Classico and soak in the Tuscan countryside one last time before heading home.

I have several nearby wineries that I recommend you visit:

• Cantina di Montalcino: a modern building where you can walk in and try the famed Brunello wines
• Poggio Antico: the best option for a tour of the wine-making process, wine tasting and pairing it with some local cheese
• Caparzo: choose from 4 wine cellar tours starting from the classic and going to the premium each includes a selection of wines served with Italian appetizers

Travel Tips for 4 Days in Tuscany

When I planned my Tuscany trips, I quickly realized that renting a car was essential. Public transport doesn’t easily connect the smaller towns, plus this will be one of the most scenic road trips you will take in Italy.

Speaking of scenic roads, I recommend Crete Senesi Vista and La Foce for your day trip. You won’t anything more spectacular than this!

Tuscany is huge—you won’t see it all in four days, so prioritize a few areas. That’s one of the reasons why I’d skip Florence and Pisa Leaning Tower, especially if you’re craving a quieter, more authentic experience.

If you’d rather include these well-known destinations in your trip and want to see how that would adjust your plans, take a look at the other itineraries I’ve designed that feature them.

• two days in Tuscany
• three days in Tuscany
• five days in Tuscany

Timing matters too. Shoulder seasons, like late spring or early autumn, offer mild weather, beautiful scenery, and fewer tourists. If you can help it, I would avoid the summer altogether.

No matter the time of year, I recommend pre-booking wine tours, especially at popular wineries, as spots fill up quickly. Similarly, if there’s a particular restaurant or dining experience you don’t want to miss, be sure to make a reservation well in advance.