Tuscany Road Trip: One Week Itinerary
Italy’s Tuscany region is truly a little slice of heaven on earth and a road trip is the best way to take it all in.
It boasts sprawling countryside views of family-owned vineyards with medieval hilltop towns that are so well preserved you’ll be convinced you’ve stepped back in time sprinkled throughout the region.
A week in Tuscany is perfect for a romantic getaway, a family trip, or a week spent catching up with friends drinking chianti and watching the sunset.
We just returned from our own week-long road trip adventure through the Italian countryside so I’m here to share the highlights and my best tips for where to go, what to eat and how to get around Tuscany.
Day 1: Montepulciano and Montalcino
Once you’ve arrived in Italy, it’s time to hit the ground running with a day of exploring to keep your energy high!
The drive to Montepulciano from Florence is about 1 hour and 30 minutes and the drive from Rome is about 2 hours and 15 minutes.
Montepulciano is a Renaissance hilltown on the ridge that divides the Val D’Orcia from the Val di Chiana.
We had lunch at Caffe Poliziano in Montepulciano where we indulged in some tagliatelle pasta and a glass of local wine.
After lunch, we walked around gazing into shops that sold ceramics, postcards and more.
Fun fact:
the iconic scene from Twilight: New Moon where Bella stops Edward from revealing his true identity was filmed here.
From Montepulciano we drove to “the Brunello town,” Montalcino.
As you may be able to guess, this town produces Brunello di Montalcino, one of the most famous red wines in the world.
This medieval hilltop town was built in 1361 and is made up of steep, narrow streets where you can see amazing views of Tuscany.
Montalcino
We chose to spend one night here and stayed at the B&B Le Scalette di Piazza.
This was an adorable bed and breakfast right in the heart of town (just as a heads up you’ll need to walk down many stairs to get here, so plan accordingly with your luggage and arrival) with self-check-in.
In the afternoon, we did a wine tasting and aperitivo at Enoteca di Piazza. They had a few different tasting options and we chose to sample local Brunellos.
After that, we were in search of somewhere to grab a light dinner and we had a wonderful meal at Il Moro.
We only ordered bruschetta and a secondi course, but they also brought over some biscotti and limoncello shots for us like we were old friends.
Not to mention, the views were amazing. Try to get here right when they open or reserve a table outside if possible.
We got the sense that most people do day trips to Montalcino and Montepulciano so to be able to wander a nearly empty Montalcino in the evening was super cool.
Day 2: Drive to Siena
Breakfast was included at Le Scalette di Piazza so we ate in the morning before bringing the car around to load in our bags.
The woman who was working during breakfast in the morning made me a cappuccino and asked what our plans were for the rest of the day.
She recommended that we check out the town of San Gimignano, which worked out perfectly since we had some time before we could check into our hotel in Siena.
We drove to the town which is about mid-way between Siena and Florence.
San Gimignano
San Gimignano is known as the “medieval Manhattan” because of its many tall towers—13 of which still survive today from the original town.
We grabbed lunch at a restaurant that was part of Hotel La Cisterna (I am 99% sure) and I’ll go ahead and dub this the best pizza we tried all week!
It was wood-fired and delicious made with fresh and local ingredients that just hit the spot.
Plus, we were able to sit in the piazza and people watch, which is always my preferred way to eat a meal.
After wandering for a bit and grabbing some gelato, we got back in the car and continued our drive to Siena.
We checked into our hotel Palazzo Ravizza (my favorite place we stayed during the trip!) and took a walk around to explore the area.
The center of Siena is called Piazza del Campo which is actually home to the famous horse race, Palio, which happens once in July and once in August.
The shell-shaped piazza is divided into nine sections in memory of the Nine Lords who ruled at the end of the 13th century.
On our first day we chose to visit the Siena Cathedral and we were lucky to visit during a time when the floors were uncovered.
The floors feature works by renaissance masters and are usually covered to protect them from wear and tear over time.
However, for a few weeks of the year they will uncover the floors so visitors can see the designs.
Construction of the cathedral began in the late 1100’s and continued for two centuries. It is truly amazing inside, with artwork in every corner.
For dinner we stumbled across Le Campane where I tried beef tartare with truffles and a cacio e pepe—both of which were delicious.
Day 3: Cooking class in Siena
For our first full day in Siena, we first decided to climb Torre di Mangia.
The clock tower in the center of Piazza del Campo stands at 102 meters tall and is one of Siena’s most recognizable landmarks.
Once you climb nearly 500 steps (in some tight hallways), you’ll be treated to panoramic views of Siena and beyond.
I’d definitely recommend arriving right when they open at 10am (a line was even forming 15 minutes before that) because tickets tend to sell out throughout the day.
Plus, in the summer months it will only get hotter as the day goes on so you’ll be less cranky if you can check the climb off your list early in the day.
From there we walked around for a bit and grabbed a cappuccino and made our way to the northern part of the city for a cooking class.
I’ve been wanting to learn more about making homemade pasta, so what better place to learn than in Tuscany?
Here is the class that we booked through Viator and it ended up being amazing.
There were about a dozen of us in the class and our instructor was very clear and helpful.
We made three different pastas and tiramisu (to be fair, they prepared most of the tiramisu in advance, which I imagine would have been tricky to teach and perfect on the first try) but the pastas were all us!
They took the pastas into the kitchen where they prepared sauces and then served them to us family style with wine included.
Once again, we weren’t super hungry by the time dinner rolled around, so we simply ordered an aperitivo board with some snacks at a spot near our hotel.
To rave about our hotel for just a moment, the best part was definitely the view from the backyard overlooking the sprawling Tuscan countryside.
We loved sitting back here and you could even order drinks from the bar if you wanted or bring your breakfast out back in the mornings.
Day 4: Winery tour in the Chianti region
Andrew got a break from driving on day four while we took a day trip to the Chianti region.
We found this trip on Viator and our guide brought us to three different wine tastings and we even got to explore a castle and some hidden gems in the region we never would have found on our own.
Our guide explained all of the various certifications and details that a wine must have to be considered Chianti Classico—from the percentage of Sangiovese grapes to the black rooster on the label.
We had a wonderful lunch at a family-owned vineyard called Azienda Agricola Casanova di Bricciano Gaiole.
It was definitely the highlight of the day. I mean, look at the view!!
The wines were all amazing and I left feeling like I learned a lot about the wine and the region—I’d highly suggest checking this one out.
Once again, we weren’t too hungry when dinner rolled around so we stumbled upon a local spot where we ordered arancini and pizza to end off the day.
Day 5: Drive to Florence
I spent one last lovely morning reading in the courtyard of our hotel while Andrew went for a morning run before we checked out of Palazzo Ravizza.
We drove to our final destination of the trip: Florence!
I was so excited to return to Florence. If you’re a long-time reader of the blog I’ve been to Florence twice before (check out those blog posts here and here) and it’s truly a city that has my heart.
We arrived in Florence and dropped off our rental car at a garage not too far from our hotel.
By this point we didn’t need it anymore, but if you are driving back to the airport in Rome, you may want to find a hotel in Florence with parking.
In Florence we stayed at the Borghese Palace Art Hotel, which was conveniently located a few blocks from Piazza Vecchio and the Uffizi gallery.
We were in Florence June 13th and 14th and the temperatures were in the upper 90s so definitely keep the weather in mind when you’re planning your trip and activities!
Since it was so hot, we decided to grab sandwiches at All’Antico Vinaio before spending the rest of the day inside of the air conditioned Uffizi Gallery.
All’Antico Vinaio
All’Antico Vinaio was a spot my friends who were studying abroad had discovered in Florence back in 2015 and it has now expanded to many other locations in Italy and worldwide.
We even have a few in NYC now so you don’t have to go too far to experience it, but I wanted Andrew to see and try the original location.
I ordered a sandwich with prosciutto, mozzarella, tomato and basil that was so good!
We were able to purchase tickets right before entering and we wandered throughout the Uffizi galleries for a few hours, viewing works from Michalangelo, Botticelli, Raphael, da Vinci, and more.
If you’re looking for the highlights at the museum, check out this list.
We also stopped by a traditional Florentine wine window where I ordered an Aperol Spritz that was delicious. These are all over the city, just search “wine window” on your phone!
That evening we finally decided to go out for a big meal and were able to get into Osteria del Pronconsolo with no reservation.
We ordered the bistecca fiorentina (a must if you’re in Florence!) and shared some bruschetta and a bottle of Chianti classico.
Day 6: Museum hopping in Florence
On our last day in Florence I decided to do something that I hadn’t done in years, which was to book a local photographer to take some photos of us in the city.
I found our photographer through a website called Local Lens but you can also book them through AirBnB experiences, Viator, or by simply finding a photographer you like on Instagram.
We did a 30-minute session and managed to cover lots of ground from the Ponte Vecchio to the Duomo.
I can’t wait to look back on these photos years later and remember this trip.
Before it got too hot later in the day, we changed at the hotel. Then, we crossed the Arno to check out the Piazza Michaelangelo.
This is probably the best place in Florence to see panoramic views of the city—the best part? It’s free!
For lunch we grabbed sandwiches from a shop called Pino’s.
There was a line but nothing compared to All’Antico Vinaio from the previous day.
My sandwich had ham, brie, and truffle oil. So simple but soooooo good.
In the afternoon the heat was really hot (if you can believe it) so we took the opportunity to visit the Galleria dell’Accademia to see Michelanglo’s David and some other amazing sculptures.
Fun fact: one of my favorite parts of this gallery is looking at Michelangelo’s unfinished sculptures leading up to the David because you can truly get a look at his process.
Before grabbing dinner, we decided to check out the Salvatore Ferragamo museum at my request and this was such a delightful surprise.
They had so many of his archival shoe designs on display and I learned a lot about Ferragamo’s history that I didn’t know.
He spent quite a bit of time in California and then became a go-to shoe designer for some of Hollywood’s brightest stars including Audrey Hepburn.
Ferragamo also registered over 300+ patents for his shoe designs and the room that displayed them all was incredible to see.
Don’t laugh but for dinner we actually went to a Mexican restaurant. We were pasta-d out by the end of the trip.
Day 7: Travel day
On the last day we traveled home! We ended up taking a taxi from our hotel to the Florence airport and connecting through Frankfurt to get home.
You could also take the train or drive to Rome and fly out of FCO.
We were sad to leave but this felt like the right amount of time for our Tuscan road trip and we were able to see SO much!
I had a blast exploring with Andrew as always and I thank him for doing all of the driving on this trip and indulging me in our photo shoot (as you may have guessed that was NOT his idea lol).
I hope you’ve enjoyed reading through our itinerary and that you’ve found some inspiration for what to do in Tuscany!
Getting to and around Italy:
- Flying into Rome will give you the most direct flights and get you close to the destinations but if you’re in Europe already or don’t mind connecting you can also fly into Florence to be closer to most of the spots on the itinerary.
- Check to see if you need an international driver’s permit to drive in Italy.
- Driving near these hilltop towns is no joke with fast drivers and narrow streets—look up routes, Italian traffic signs and parking options ahead of time so you’re not stressed in the moment.
General Italy travel tips:
- In the summer months, it can get incredibly hot and the bugs will come out! I’d recommend staying hydrated by drinking lots of water, wearing sunscreen and bug spray and even bringing a mini fan if you get super hot.
- We ended up purchasing some large water bottles from a local grocery store to keep in our car and hotel rooms so we always had water on hand.
- Most restaurants close between 2pm-7pm between lunch and dinner so keep this in mind especially in the smaller towns.
- Watch out for pickpockets! Bring a crossbody bag with a zip top to reduce your chances of getting your wallet or phone snatched.
Have you visited Tuscany? Tell me about it in the comments!
yours,
Austen
Watch our trip vlog:
