If you’re planning a getaway to the most picturesque region of Italy, here’s my 6-day itinerary through Tuscany. Winding roads through hills, medieval villages, great wine, and unforgettable pasta.
Before visiting Tuscany, I already had a feeling I was going to love it… and I did. We did this trip by car from Barcelona, passing through various parts of Italy and France until reaching this dreamy region. We decided to base ourselves in a rural house near Arezzo and from there, explore different villages each day.
In this 6-day Tuscany itinerary, I’ll share the full route with ideas and accommodation suggestions at each stop, in case you prefer to change base as you go.
Day 1: Pisa, car rental, and arrival at your accommodation
Recommended Accommodation in Pisa: Hotel Repubblica Marinara or Il B&B dei viaggiatori
Our first stop on the Tuscany road trip was Pisa. If you’re flying in, I recommend arriving in this city and renting a car at the airport.
Pisa doesn’t have much to see beyond its famous Leaning Tower, so a couple of hours is enough. I recommend taking a guided tour of the Cathedral + Leaning Tower or a walking tour to get a bit of historical context.
Depending on your arrival time, you can either stay the night in Pisa or continue driving to a countryside accommodation in a Tuscan village.
We visited Pisa in the morning and then drove to a rural lodge near Arezzo, a dreamlike place surrounded by olive groves and vineyards. We based ourselves there to explore the villages and get some rest as well.
Day 2: Montalcino, Montepulciano & Val d’Orcia
Recommended accommodation: Palazzo Massaini or Mastrojanni Relais
MONTALCINO
Start the day visiting Montalcino, birthplace of the famous Brunello wine. It’s a small village but full of charm.
MONTEPULCIANO
Then, head to Montepulciano, another hilltop medieval town. It offers stunning views and quaint streets filled with restaurants and wine shops featuring local vintages.
End the day in Val d’Orcia, watching the sunset from the iconic viewpoint with aligned cypress trees — a picture-perfect scene (you’ll probably recall the one from Gladiator). This valley is a UNESCO World Heritage Site and absolutely breathtaking. You’ll find many scenic spots for photo stops — I’ve marked the exact location on the map below.
There are also many rural hotels in Val d’Orcia with incredible scenery, so it’s a great option to stay one or two nights in this area.
Day 3: Siena, Monteriggioni & San Gimignano
Recommended accommodation: Hotel Minerva (Siena) or Mormoraia (San Gimignano)
SIENA
Start the day in Siena — don’t miss the stunning Siena Cathedral and the Piazza del Campo. Siena is a large and beautiful city. It’s also a good central base for exploring Tuscany thanks to its location and wide range of accommodation.
There are plenty of restaurants in Siena. We had an amazing lunch with homemade pasta at Compagnia dei Vinattieri.
MONTERIGGIONI
Then, make a quick stop in Monteriggioni, a fortified village that seems frozen in time. It’s very small, so it won’t take long to visit.
SAN GIMIGNANO
In the afternoon, visit San Gimignano, arguably Tuscany’s most famous village. It’s one of the best-preserved medieval towns, still boasting many of its original towers (it once had 72!).
Don’t miss the legendary Gelateria Dondoli — one of the best gelatos I’ve had in Italy.
Day 4: Arezzo & hot springs
Recommended acconmodation:Hotel Le Capanne
Since we were staying near Arezzo, we dedicated this day to exploring the city. I found it far less touristy than other towns in the region, but it has plenty of history and things to see — definitely worth a visit if you’re nearby!
And the food in Arezzo? Amazing. I had delicious pasta at Antica Osteria l’Agania and the best pistachio gelato of my life at Cremeria Cecconi.
Another plan for this day could be a visit to the natural hot springs of Bagno Vignoni — the perfect way to unwind.
Days 5 & 6: Florence
Recommended accommodation: Residenza d’epoca Poliziano or Relais Piazza Signoria
The final stop of this itinerary is Florence, the jewel of Tuscany.
I recommend spending at least 2 days in Florence, where you can’t miss the Duomo, the Ponte Vecchio, and several of its museums. It’s truly one of the most beautiful cities in Italy, with history around every corner.
To get more insight into Florence’s history, I suggest joining this guided walking tour.
Other Places to Visit in Tuscany
-
Pienza: A small town just before Montepulciano. I didn’t get a chance to visit, but it’s worth adding if you have time.
-
Lucca: Close to Pisa, with bike-friendly walls and a vibrant old town.
-
Volterra: Less touristy than other towns, with charming medieval vibes and Etruscan ruins.
-
Saturnia Hot Springs: Natural thermal pools surrounded by nature — free and open year-round.
-
Chianti: A region of its own, famous for rolling vineyards, castles, and wineries. Perfect for a day of wine tastings and scenic lunches.
Map of the Tuscany Itinerary
On the map, I’ve marked all the places mentioned in the post, including hotels and restaurants I visited.
Tips for Traveling in Tuscany
-
Rent a car if you can. It’s the best way to move between villages and enjoy the journey at your own pace. I recommend using Booking, a site that compares prices from various car rental companies and usually offers the best deal.
-
Book your accommodation in advance, especially during high season. It’s a popular tourist area and the best spots fill up quickly.
-
Base yourself or hotel-hop? There’s no one right way to do this trip. We wanted to relax and experience a bit of Tuscan rural life, so we stayed 5 nights in the same place near Arezzo + 2 nights in Florence. But switching hotels can be convenient for covering less distance each day.
-
Don’t over-plan your itinerary. Part of Tuscany’s charm is slowing down, being spontaneous, and enjoying the dolce vita without a schedule.
Can You Visit Tuscany Without a Car?
If you can’t rent a car or have fewer days but still want to see the region, you can take a day trip from Florence. Some options include:
-
-
Pisa, Siena and San Gimignano Day Trip from Florence: A full-day trip including transport, english-speaking guide, lunch, entrance to Siena’s Cathedral, english guided tour of Siena, and winery visit. One of the most complete tours for just €55.
-
Pisa, Siena, San Gimignano & Chianti Day Trip from Florence: a complete tour including stops in Siena, San Gimignano, Chianti, and Pisa. Round-trip transportation by air-conditioned bus from Florence is included.
-
Tuscany’s Gastronomy
Tuscan cuisine is simple, flavorful, and based on local ingredients. Some must-try dishes include:
-
Pici: A thick, handmade pasta typical of the region, served with ragù or garlic and tomato sauce.
-
Truffle (tartufo) pasta -
Ribollita: A hearty soup made with bread, vegetables, and legumes.
-
Bistecca alla Fiorentina: A classic for meat lovers — giant and juicy.
-
Wines: Don’t miss out on Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano.
Other useful posts about Europe:
- Florence in 2 days itinerary
- Where to stay in Florence
- Things to do in Rome in 3 days
- What to do in Milan in 3 days
- What to see in Copenhagen in 3 days
- What to see in Barcelona in 3 days
- What to see in London in 4 days
