Romantic 7 Day Tuscany Road Trip

Tuscany Road Trip Itinerary

This Tuscany road trip itinerary was mostly decided based on our general route from Florence South to Rome and finding dots on the map that sort of fit into that route. The road trip came during month four of our around the world trip, and we were simultaneously stressed over how much Italy had broken our budget–smashed it to pieces, really–and feeling like we needed to get the most out of the time we had left. Spending 7 days in Tuscany did not alleviate our budget concerns, but it certainly gave us all the happy heart feels that we needed.

It also happened to be the week of Valentine’s Day which, we normally ignore, but being that we were on a road trip in Tuscany things shifted a bit. Maybe it was the love in the Italian air or the major bummers about ending our trip, but we decided to throw in the towel and actually celebrate for once.

Enter our week-long road trip in Tuscany. Below is the 7 day Tuscany road trip itinerary we created, taking the slow route from Florence to Rome, enjoying the beauty and each other as we went. We won’t discuss Florence in this post, although we have strong opinions on it, as it was not a part of our road trip. If you are visiting there first we have a beautiful running route that you cannot miss. Instead, below, you will find information on the Chianti region, Siena, and Cortona including where to stay, eat, and find scenic running routes.

Tuscany Road Trip Itinerary

Tuscany Road Couple Sitting Together

Tuscany Roadtrip: Days 1-3 Chianti Region

As soon as we knew we were going to Tuscany we knew we wanted to stay in a vineyard. We selected an agriturismo for this portion of the trip partially because we love the idea of supporting local family owned business but mostly because it was a vineyard and we wanted easy access to all the wine. Breakfast was made to order every morning and served on a beautiful wooden table in the main building. It’s worth noting that this was not included in the price and was fairly expensive.

Hike in Chianti couple in field
Stopped off at a beautiful roadside hike on the way to the vineyard

Day 1 Florence to Greve in Chianti

We picked up our rental car in Florence and spent a stressful 20 minutes navigating the ultra-narrow streets out of the city, our first lesson that driving in Tuscany is not easy. Once on the highway, the drive turned lovely. The vineyard we stayed at was a bit outside the town of Greve in Chianti making it about an hour drive. We did not stop off anywhere on this portion because we were excited to get out of Florence and into the heart of Tuscany.

Our actual first stop on our Tuscany road trip was a lovely little hike on our way to Chianti. At the Area Naturale Le Balze, we stopped and got some fresh air before a night of wine and cheese.

Night 1 :Quereceto di Castellina Vineyard

Sunsets on the vineyard

Day 2 Greve in Chianti

We made good use of a beautiful sunny day and spent it touring the area. Many of Tuscany’s vineyards were closed for the winter season, so we spent the day on beautiful, winding roads that lined gorgeous valleys showing off the more jagged landscape that this part of Tuscany is known for.

Where to Eat in the Chianti Region

The farmers market was happening in the square in Greve in Chianti. It ended up being the best food we ate in this region. The square was lined with bakeries and salumerias that had been in business for decades, some longer. On a leisurely stroll, we picked up all the supplies one could hope to ever need in Tuscany.

We ate brilliantly red Sicilian strawberries, roasted porchetta sandwiches on soft, freshly baked bread, and happily munched on cheese’s named for Italian words that we could not pronounce. Even in winter, the produce and access to fresh food is of the utmost importance to Italians.

Dinner was in Pieve di Panzano, Ristorante Oltre II Giardino which was just ok, not a place we’d recommend or go back to. It was winter when we went, however, and their outdoor space looks pretty magical for the summertime.

Night 2 : Quereceto di Castellina Vineyard

Piazza del Campo Siena clocktower
The Piazza del Campo in Siena

Tuscany Roadtrip: Days 3-5 Siena

Next stop on our Tuscany trip itinerary was Siena. After three days spent in the peace and quiet of the Tuscan countryside, we packed up and headed back to the city life – well, as city life as it gets in this part of the country. Siena is beautiful, absolutely stunning really. We spent two nights here, although it could have been a day trip. As much as we enjoyed wandering the narrow cobblestone streets and gazing at the ancient architecture, we only had 7 days in Tuscany and preferred the smaller Tuscan towns overall. The hotel we stayed in was perfectly fine but the on-site breakfast was downright bad. We stayed in this hotel because it was cheap and had a great location, but we wouldn’t choose it again.

Man sitting across from statue
Chianti Sculpture Park

Day 3 Greve in Chianti to Siena

On our way to Siena, we stopped at Chianti Sculpture Park and we’re incredibly surprised with how cool this place was! An entire park with sculptures from all over the world, this is such a great stop for a road trip.

Siena is tucked inside of the surrounding stone wall and centered by the Piazza del Campo. This was our first stop in the city, a beautiful and lively open space in the midst of the narrow and sometimes crowded streets. Yes, the piazza is beautiful, yes you should explore it, but more importantly, you should explore your way over to the little wooden shack on the side of it serving up Siena’s tasty fried sweet, Frittelle.

Only open in February and March, Marco Savelli’s version of this traditional Siena delight warms up the hands, mouths, and hearts of all those lucky enough to grace their doorstep. Frittelle is regionalized, made different throughout the country. In Siena it is made with sticky sweet rice and orange rinds, formed into a ball, fried to crispy perfection, and dusted with a healthy dose of sugar.

To attempt to compensate for the amount of Frittelle we crushed in a roughly 3-4 minute window, we went for a lovely run in the park around the Fortezza Medicea. It has beautiful views of the city in a short uninterrupted loop, a great option for running in Siena.

Night 3: Hotel Alma Domus

Dusty old bottles of Brunello wine

Day 4 Brunello winery tour from Siena

There are many operators offering wine tours from Siena, but we chose to follow our deep and passionate love for Brunellos. We picked “My Tours” to take us simply because they had a pamphlet at our hotel and offered the tour we wanted the day we wanted. Admittedly, there’s probably a more strategic way to do this.

My Tours picked us up from our hotel at 1:00 P.M. and took us right to Abbadia Ardenga, a beautiful, old family vineyard. With dusty bottles of wines in its cellar dating back to the 1940s and a collection of ancient wine tools, the visit to the vineyard was as much a history lesson as it was a tasting. Their Brunello was very good, and the cheese, salami, and bread snacks they gave with the tasting were delicious.

The next stop was the ultra charming little town of Montalcino where there was a second tasting at a wine store.

While this tasting allowed us to sample many different kinds of wines from different vineyards, we would have preferred going to additional vineyards instead for the price we paid for the tour.

However, the wine store staff was quite knowledgeable and friendly, and we hung out for longer than the rest of the group learning about the process and grapes of which we were so enjoying. We were taught that classic Brunello is aged in large barrels (10k liters) and that while the other common wine from this region, Rosso, is only aged for one year, Brunello is aged for five. Also, apparently locals don’t drink much Brunello themselves because it is expensive and roughly half of all the bottles, of which there are not many, are shipped abroad.

All this is fun and games until someone gets drunk. Brunello’s are no joke, and after quite a few healthy pours and a case of wine under our arm, we took to the streets of Montalcino a few sheets to the wind and walked up to a fortress on the hill for a fun sunset photo shoot that produced truly awful pictures. We met up with the rest of the tour after snagging some delicious focaccia from a little bakery and hopped back on the minivan that dropped us right back at our hotel doorstep.

The tour ran us 60 Euro/person, and we thought that the guide was great. However, we would have definitely preferred to spend the 5 hours on tour vineyard hopping instead of stopping by the one and exploring the town which was quite cute but just not what we were there for.

Night 4: Hotel Alma Domus

Frittelle in Siena
The delicious and delightful Frittelle

Where To Eat in Siena

Aside from the Frittelle mentioned, there is a notable lack of food in this portion of our trip due to budget constraints and a selection of tourist trap restaurants. Some places looked like they could have been awesome but were closed for the “holidays” (being closed for the holidays in Italy could mean anywhere from 1-4 months in the winter from what we saw, note Joe’s post on Venice).

Tuscany Road Trip: Days 5-7 Cortona

Welcome to the best part of Tuscany and one of our favorite parts of Italy period: Cortona. We’ll be totally honest here, we came to Cortona because it was the town featured in Under A Tuscan Sun and, being the touristy tourists that we have accepted that we are, we followed trusty Diane Lane to this small hillside town. I know, I know, it’s potentially the cheesiest thing we’ve ever done and we should be embarrassed but honestly, it was just too awesome to be ashamed of.  Thankfully she did not steer us wrong, and we absolutely loved our time here.

The hotel we stayed in, Le Bifore, was a splurge for us and SO worth it. It was adorable, luxurious, and perfect for a romantic night in Tuscany. We opted for the Deluxe Suite which gave us gorgeous views of the sun setting over the Tuscan hillside. The best part about staying here, though, was the manager Laura who fussed over us like a sweet Italian mother and baked homemade cakes for breakfast alongside her delicious espresso. Our last morning she baked our initials into a heart-shaped cake and we almost died from the cuteness of it all.

*As always we are very transparent about who we promote on this site and want to be clear that this was not sponsored by Le Bifore or anywhere else mentioned in this post, we just loved the hotel!

Tuscany sunset fortress

Day 5 Siena to Cortona

We turned the short drive from Siena to Cortona into a long day of sampling hot springs that were easily accessible along our road trip route. We wrote a detailed post about which springs we stopped at and how to get to them here. If there is one thing I recommend doing in Tuscany, aside from drinking all of the wine, it’s visiting these beautiful natural hot springs.

After a long day of soaking in sulfur, we arrived in Cortona in the late afternoon, and Laura hopped in the car to help us park–parking on a cobblestone hill in a space just big enough to fit our rental car was not easy (see rant on how much WE LOVE LAURA above) and watched the sunset from Piazza Garibaldi. We snacked on munchies grabbed from an Italian grocery store and drank more Brunello from the comfort of our magical hotel room.

Night 6: Le Bifore

Sunset in Cortona Tuscany
Sunset in Cortona Tuscany

Day 6 Valentine’s Day in Cortona

We started off the day going for a run through the village, panting and heaving our way up the vertical hills while we sweat out copious amounts of Brunello from the night before. Being drenched in wine sweat aside, it’s a lovely albeit challenging town for a run.

Where To Eat in Cortona

We got lucky, very lucky, in that Fett’ Unta happened to reopen on the day we were in Cortona. This very small lunch spot served the best food we ate in Tuscany for a very modest price tag. It was February, so we went the soup route – Ribollita and Artichoke with barley. These were the kinds of soup that you slurp down long after is socially acceptable and use the endless bread flow to sop up every last drop. The owners also have another restaurant in town, Osteria del Teatro, which was sadly booked up for Valentine’s Day dinner so we did not get to try it.

Instead, we ended up with a reservation at Ristorante La Loggetta. We were likely squeezed in, as our table was near the front door and, surprise, one down from where Conan O’Brian was filming for his new show. It made for a very different atmosphere than the romantic one we had envisioned for our Tuscan Valentine’s dinner but it ended being a blast. The food was not memorable, a tasting course with fairly mediocre food, but the night itself was.

We buddied up with the table next to us, a delightful Italian couple who were the only other ones in the room aside from the film crew, and the four of us proceeded to drink the bar out of wine and, later in the night, rum. We chatted with Conan, our friends made a guest appearance on the show, and we happily stumbled out of there past midnight and back to our hotel room.

Night 6: Le Bifore

Homemade cake in Tuscany
Laura’s homemade cake with J A and hearts in sugar, can you even?

Day 7 Cortona to Rome

All the wine and all the rum from the night before rolled right into the next morning making it a rough one. Sad enough to be leaving Tuscany, we were too hungover to feel much of anything and ended the trip with Alicia passed out in the passenger seat and Joe, being the MVP, driving on to Rome. We made time for one last Autogrill pitstop but otherwise ended our Tuscan road trip by sleepily pulling into Rome for a week of eating in the Trastevere neighborhood.

**Side note, if you don’t know what Autogrill is, it’s worth renting a car and driving in Tuscany just to find out.

Tips for a Tuscany Road Trip

  • Autogrill: WAY better than any roadside store in the USA. This store has fresh espresso, sandwiches, meats, and cheese and they are located roughly every 50 miles on this drive.
  • The winding roads and beautiful views did make for a bit slower driving. Italians like to go fast so be sure to let them pass you by.
  • Agritourismo: Not super prevalent in the winter but very popular in the summer. This allows you stay on actual farms while also getting a bed and breakfast type feel.
  • There is no public transportation in Tuscany. If you do not want to rent a car, there are tours to join or drivers to hire.
  • Stating the obvious, but the wine, cheese, and food from this area are some of the best in the world. Be sure to indulge.
  • A deep Tuscan tradition still exists, as the bread in Tuscany is NOT salted. Most would think this wouldn’t make a difference but it does taste different. Most restaurants will serve salted butter with bread as a substitute.
Tuscany Road Trip Itinerary

Alicia is a freelance writer, bartender, and the MLT wife! She loves running, beaches, and tiny animals.


  1. January 30, 2021 / 3:18 AM

    Thanks for the write up, we are planning to spend most of fall 2021/winter 2022/spring 2022 in Italy and these kinds of blog posts really help us narrow down where to go and stay.

  2. September 4, 2019 / 3:10 PM

    Excellent! Love the content, thank you for sharing. I added your link to my page:

  3. May 15, 2019 / 2:57 AM

    Hi Alicia, I really liked your post how you showcase the 7 days road trip along with there beautiful places. Good Job.

    • Miles Less Traveled
      May 15, 2019 / 10:39 AM

      Thanks so much Don! Glad you liked it

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