Last Updated on April 29, 2024 by Maggie McKneely

Going to Tuscany? This is the one-week Tuscany itinerary that you need.

7 Day Tuscany Itinerary

Ah, Tuscany! The land of funny-looking cypress trees, buttery breakfast brioche, and grapevine-covered hillsides. And wine, of course. There’s no question that Tuscany is one of the best regions in Italy for a road trip! My mom and I got to spend a week driving around the region and discovered that it really is just as idyllic as everyone thinks that it is.

But “Tuscany” (or “Toscana”) describes a region of Italy that’s 8900 square miles and includes hundreds of medieval hill towns worth exploring. How do you cover that much territory in a week?! Today, I’m sharing the best Tuscany itinerary based on the week-long trip that we did through Great Value Vacations. It’s perfect for getting a taste of the entire region without feeling too rushed and is perfect whether you’re traveling with buddies or doing a solo trip to Italy. Enjoy!

7 Day Tuscany Itinerary

Day 1: Land in Rome and drive to Tuscany

Although the airport in Pisa is much closer to Tuscany, it’s generally less expensive to fly into Rome’s much larger airport. So, for our purposes here, we’re going to assume that that’s where your trip will begin, and thus the beginning of this Tuscany itinerary. Because Tuscany is such a large area, and public transportation isn’t that great, the best way to get around is to rent a car. So, once you land, grab your bags, pick up your rental car, and hit the road! (But first, be sure to check out my tips for driving in Tuscany).

From Rome to Tuscany, it’s an easy 3-hour drive on the Italian “autostrada” (aka highways). You’ll drive near several Tuscan towns, but I encourage you to resist the urge to stop at too many. The towns take longer to explore than you think. I had originally planned on us stopping in three towns on our way from the airport to our “agriturismo” (the Tuscan version of a B&B). But, we only made it to two.

The first town that makes a perfect stop on your drive on Day 1 is Civita di Bagnoregio. It’s actually a ghost town – the cliffs surrounding the city keep eroding, so it’s not safe or practical to live there. But it’s a fascinating place and is unlike anything else in Tuscany. It’s tiny, so it doesn’t take long to explore, but you’ll be happy you made the stop.

Tuscany itinerary

Civita di Bagnoregio

Note: You have to park at the top (it’s permit-only parking at the bottom), and from there it’s about a mile down the road and then up the footpath into the town.

The second town is beautiful Orvieto. Best known for its black-and-white striped cathedral, this little town in Umbria makes for a great place to grab a bite to eat and stretch your legs before getting back on the road.

Day 2: Florence

No Tuscany trip itinerary is complete without two days spent in the magnificent city of Florence. But driving and parking in the city can be an expensive nightmare; once you’re in Florence, it’s one of the most walkable cities in the world. But to get there, the locals suggested we use the Tramvia instead, which turned out to be awesome. Here’s how to do it:

  • Park at Viuzzo delle Case Nuovo, Florence
    • There’s a giant free parking lot in front of the Coop. Walk across the street to the Tramvia station. Get a ticket at the machine at the end of the platform (1.20 euros per person) and take the tram to Alamanni-Stazione. From there, it’s a five-minute walk to Florence’s city center.
    • Don’t forget to get your tickets! If you’re caught without them, you’ll get slapped with a nasty fine.

First things first once you’re in Florence: find coffee and brioche. This daily treat became a ritual for us every morning we were in Tuscany. I personally never eat creme-filled croissants at home in the US, or really pastries of any kind very often. But in Italy, the brioche are just so divinely flaky and buttery and they are all made fresh that morning. And we found that they kept us full until the afternoon! You can’t get brioche like that outside of Italy, so take advantage of it. And don’t order a mug of American drip coffee; this is Italy, get the cappuccino.

Tuscany itinerary

Cappuccino and jam-filled brioche

After you track down your morning snack, head to Santa Maria dei Fiore, more commonly known as simply the Duomo. If you want to see the inside of Florence’s famous Duomo, get there early!!! It opens at 10 AM, but the line starts forming before then. There was a very long line the day we went, and it was cold and pouring rain. I can only imagine what it’s like in nice weather, but it’s worth it.

Florence's Duomo

The Duomo

If you’re up to it, I also suggest climbing the 400+ stairs to the top of the dome. You’ll get an incredible view of the entire city, and you’ll get to see Bruneschelli’s dome, both inside and out, up close and personal, which is pretty cool! If you want to do this, you do have to get tickets for a reserved time slot in advance.

Florence's Duomo

From the top of the Duomo

Florence’s Duomo Visitor Information:
  • Hours: 10 AM – 4:30 PM
  • Admission: Entry to the main cathedral chamber is free, but there is a fee for a combined ticket to the connected museums and to climb to the dome
    • Go here for advanced tickets to the dome

As a reward for climbing the dome, treat yourself with gelato from Edoardo, located right near the Duomo. Everything here is 100% homemade and organic. They’re listed as one of the best gelato shops in Florence, and after you try their honey-lavender, cinnamon, or pistachio on a homemade cone, you’ll understand why.

After the Duomo, head to the Mercato Centrale for a lunch of authentic Italian food (yes, after gelato, but you’re in Italy, so who cares?). This is Florence’s historic 2-story farmer’s market. There are tons of authentic Florentine vendors here, but a warning: many of them don’t speak a lot of English. We accidentally bought 40 euros worth of meat and cheese here because we couldn’t figure out how to communicate what we wanted to buy (video proof here). It was a hilarious stereotypical tourist moment, but learn from us and brush up on your Italian before you go.

Next on the itinerary is another church, Santa Croce. This is the final resting place for Michelangelo, Dante, Machiavelli, and Galileo! That’s a lot of star power in one location. Santa Croce is much smaller and less well-known than its famous neighbor, which means it’s also less busy.  Personally, I found this church to be far more fascinating than the Duomo; a trip to this hidden gem is definitely worth your time.

Santa Croce

Santa Croce

Santa Croce Visitor Information:
  • Admission: €8
    • Purchase tickets here

Afterward, spend some time wandering around and find a cute little sidewalk cafe (or one of these restaurants) for dinner. Then head back to the train station to catch the Tramvia back to your car.

Day 3: Florence – again

Do you know what else is in Florence besides the Duomo? Yeah, The David. So that should be first on your agenda today after you arrive in town via the Tramvia again, and after you find your coffee and brioche. The David is located inside the Galleria dell’Academia. For serious art lovers, this is a small museum with several interesting pieces, but for the average person (like my Mom and I) The David is the most important attraction, so there’s no need to spend a lot of time here.

The David

Hi, David

Galleria dell’Academia Visitor Information: 
  • Hours: Open Tuesday-Sunday,  9 AM – 6:15 PM
  • Admission: Full: €12
    • Go here to see if you qualify for a reduced or free ticket
    • You can pre-purchase tickets online here, but it will cost you an extra €4 to do so

After seeing The David, you should make your way across town to Piazzale Michelangelo. It’s a park located on the other side of the river above the city. Every photo you’ve ever seen of the famous Florentine skyline was taken from here, so it’s a must-do part of your Tuscany itinerary.

Piazzale Michelangelo

From Piazzale Michelangelo

From here, you have several options, depending on how much time you have and your interests. The Uffizi Gallery is one of the most famous art galleries in the world. I included it on our original agenda, but, as I said, my mom and I aren’t art gallery people. When we saw the line stretching for half a mile from the ticket booth, we decided to pass on it.

There are also the Boboli Gardens, located near the Piazzale Michelangelo. We ran out of time to go here, but the pictures look beautiful!

The famous Ponte Vecchio is in this area of town as well. If you go near sunset, you can get some pretty stellar pictures of Florence’s oldest bridge.

Florence is also the perfect place to shop for your Italian leather souvenirs. There are tons of leather shops, and most of them are the same as the next. But we found one, Gabi, that carries bags and jackets that you won’t find in any other leather store. The husband and wife team (he’s Italian, she’s Australian) are extremely friendly and work hard to make sure that their store really is completely different from every other one in Florence.

Day 4: Siena and San Gimignano

Day 4 of your itinerary includes a couple of the most beautiful villages in Tuscany. The first, Siena, is a town I wish we had spent more time in. It’s definitely worth spending at least half a day here. The walled portion of the city, like many Tuscan towns, feels like a step back in time to medieval days. Except that modern-day Siena is a bustling upscale city with shops such as Gucci and Prada!

Your first stop in Siena, besides coffee and brioche, should be the unbelievable Siena Cathedral. If you’ve spent any time in Italy, you’ve doubtless been in a number of impressive churches, but the one in Siena is arguably the most ornate. It even rivals the Vatican.

Siena Cathedral

So much artwork in this cathedral!

Siena Cathedral Visitor Information:
  • Admission: The “Opa Si” Pass includes entry to all of the museum’s complexes, excluding the rooftop tour
    • Adults: €20
    • Children 7-11 years old: €5
    • Go here for a full list of ticket options

There are a number of other historical attractions in Siena that you can find listed online, but my other suggested stop is a sort of random one: the Nino and Friends chocolate shop is located just below the cathedral. What makes this shop so amazing is not that they sell chocolate, but that they convince you to buy it by bringing out tray upon tray upon tray of free samples. Just when we thought we had tasted everything in the store, out came the salesman with more. For my American readers, it’s like shopping at Costco, but with high-end desserts instead of microwavable taquitos. You won’t need to find lunch if you make this stop!

After you’re finished exploring Siena, head north to another famous Tuscan town: San Gimignano (aka the town that only Italians can properly pronounce). This walled city has the most distinctive skyline of any in Tuscany, with 14 of its 72 original towers still standing. Wandering around San Gimignano truly feels like walking through a castle.

This is another town I wish that we had left more time for. We almost didn’t have any time at all, but made a quick stop specifically for gelato. There’s a shop here, Gelateria Dondoli, run by a guy who was the gelato world champion for a couple of years, but the shop had already closed for the day when we got there (we were extremely upset about this, as you can imagine haha). But just from our quick nighttime jaunt through the town I could tell that it was adorable and would be worth exploring.

At the end of the day, head to one of the local wineries, such as Guardastelle, for a tour and tasting before heading back to your agriturismo. Because really, no Tuscany itinerary is complete without a wine tasting!

Day 5: Val d’Orcia, Montalcino, Montepulciano

Val d’Orcia is the area of Tuscany that everyone imagines – the vibrant green hillsides, fields of sunflowers, and hilltop estates surrounded by cypress trees. It’s the region that looks like it’s straight out of a Renaissance painting, making it one of the best places to visit in Tuscany. There are several towns here, but we stopped at two that should definitely be on your itinerary.

Montepulciano is situated high above the landscape. It’s often called the prettiest town in Tuscany, and with so many pretty towns, that’s really saying something. But with the vistas of Val d’Orcia and its own beautiful medieval architecture, it truly is stunning. It’s definitely one of Tuscany’s best-hidden gems. Finding parking is the worst part about visiting this town, but if you can find a spot and are able to spend some time exploring here, you will be rewarded.

Montalcino is another high hilltop town, located about 30 minutes from Montepulciano. In addition to the ancient town, Montalcino is also home to an imposing fortress – yes, an actual fortress with gates and turrets and everything you expect from a fortress! But Montalcino is best known for being the home of Brunello di Montalcino, one of Tuscany’s most famous wines.


It was REALLY foggy when we were in Montalcino

The winery we went to in Montalcino was our absolute favorite of the trip. Solaria is an all-female-run winery, which is a rarity in the male-dominated Italian wine industry. Patrizia Cencioni’s grandfather was one of the founders of the Brunello wine, but instead of inheriting his farm, she went off and started her own in 1981. Today, she runs all aspects of the winery, including the wine-making, with help from her daughters. Her oldest, Arianna, was our tour guide, and she was absolutely delightful. Plus, the wine was fantastic. 10/10 absolutely recommend it.

Check out my full post on this amazing Tuscan winery!

Solaria Winery

Solaria’s wine cellar

Day 6: Barga, Massa, and Pisa

Did you know that Tuscany includes the southernmost portion of the Alps? Well, now you do, and today is the day you get to drive in them!

By the way, if at any point you desperately need your morning snack before you arrive somewhere with a cafe: the best brioche we got in Tuscany was actually from a gas station. I know, it sounds bizarre. But this gas station had a cafe attached to it and I’m telling you, that brioche was AMAZING. So know that gas stations are a viable option for getting your daily pastry fix.

The first town on Day 6 of your Tuscany itinerary is the beautiful village of Barga. The drive to Barga is worth the trip all by itself, as you’ll take roads that follow gushing rivers, go through lush green valleys, and wind their way under mountain peaks. I haven’t yet been to Germany, but it looked like how I imagine Germany looks.

Tuscany itinerary

On the road to Barga

But then you get to Barga, and it’s just as lovely as the drive. Like every Tuscan town, it’s situated on a hilltop, only this hilltop is surrounded by much larger, often snow-covered, mountains. There are a number of historical palaces (yes, palaces) to explore here, as well as the token cathedral.

From Barga, your next stop should be the beach at Massa. There are two different ways to get there. You can retrace your steps and head back down the mountain the way you got to Barga. Or, there’s a winding road that goes over the mountains. ABSOLUTELY DO NOT DO THIS IF IT’S SNOWING. Ha, we tried that, and almost drove off a mountain. Literally. Here’s the video.

Barga, Italy

Trying to drive on snow-covered alpine roads…not my greatest idea LOL

But if the weather is right, this would be an incredible drive. You go through several more mountain towns before leaving civilization to climb up and over the famous Italian marble mountains of Carrara, before descending via hairpin turns into Massa on the other side. It’s not for the faint of heart, but it’s also not the worst road we drove on in Tuscany either. If you want amazing mountain views, it’s worth doing.

But however you go, Marina di Massa is your destination. Located on the eastern coast of Italy, Massa is one of Tuscany’s beach towns. The marina has a long pier that juts out into the ocean, which is a lovely place for a stroll. Or you can even kick off your shoes and wander down the beach.

Massa, Italy

The Mediterranean 🙂 If you squint, you might be able to see Cinque Terre way off in the distance!


Massa, Italy

Happy to be by the ocean and in the sunlight!

From Massa, head to Pisa. Honestly, I expected Pisa to be extremely touristy and the sort of place that you run in, get the picture of the tower, and leave. But Pisa was far more interesting than I expected. There’s much more to it than just the Leaning Tower! The historical park containing the tower has a number of other fascinating buildings worth exploring. You still don’t need to spend more than a couple of hours here, maximum (in fact, here’s a great itinerary for a half-day trip to Pisa from Florence). But don’t skip it for fear of it being a tourist trap. I mean, you’re this close to it – might as well go, right?

Leaning Tower of Pisa

Leaning Tower of Pisa

And one without other tourists in the shot!

Leaning Tower Visitor Information:
  • Admission: Entry to the historic area, including the Tower, is free. But if you want to climb the tower itself, tickets are €18.
    • It’s best to reserve tickets ahead of time here, as the line can be very long. But it is an extra €6 to book online.
    • If you want to book a guided tour, go here.
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Since it’s your last night of this Tuscany itinerary, it’s time to splurge on the one dish that Tuscany is known for: Bistecca alla Fiorentina. Basically, it’s a steak. But it’s the most incredible steak you’ll ever have. The piece of meat that they serve is huge; my mom and I split it and still couldn’t eat the whole thing. But it was DELICIOUS.

Bistecca alla Fiorentina

The plate on the left = an entire half of a cow, I’m pretty sure

Day 7: Fly home

Day 7 is the worst part of your Tuscany itinerary, unfortunately. I don’t really need to explain this depressing day, do I? The good news is: the Rome airport has cappuccinos and brioche! 😀


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Headed to the land of cypress trees, wine, and incredible food? Check out this perfect one-week Tuscany itinerary! #italy #travel #tuscany #roadtrip #florence  Headed to the land of cypress trees, wine, and incredible food? Check out this perfect one-week Tuscany itinerary! #italy #travel #tuscany #roadtrip #florence  Headed to the land of cypress trees, wine, and incredible food? Check out this perfect one-week Tuscany itinerary! #italy #travel #tuscany #roadtrip #florence



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