A Tuscan Road Trip – Our Favorite Pit Stops

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Dream with me for a bit. Imagine green, infinite landscapes covered in a layer of fog just as the sun starts to rise. Imagine old, historic brick monasteries on a hilltop surrounded by old, colorful shops. Imagine climbing to the top of an Italian church’s tower and breathing in the most breathtaking view of the town. Imagine freshly made pasta at your table along with crackling, warm bread that you can dip into the homemade, 100 year-old secret pasta sauce. And, finally, add in a bottle of wine, only found into that region, hyperlocal, being poured into your glass to top off your experience.  When I think about my trip to Tuscany, I think of all of these things. I had dreamed of visiting this Italian region for years and my expectations were met and then –surpassed.

We rented a car in Lucca, Italy and hit the road through several small Tuscan towns over 5 days. Driving is the best way to see Tuscany as public transportation isn’t very common in the small villages or near wineries. We flew in and out of Pisa (rental cars are cheapest if picked up and dropped off in the same location).

Map Italy

Here’s a look at our 5-day road trip & recommended stops along the way. We hope it inspires you to take a trip to Tuscany one day!



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  • Our first and favorite stop in Tuscany (we drove straight here from Pisa’s airport)
  • We stayed: 1 night
  • The city is surrounded by an old, historic brick wall (set up in a circular shape) – it’s small enough to walk around the inner rim of the city within an hour or two (we did!)
  • Town can be quiet at night (many shops shutdown) especially on Sunday when we were there


  • ACTIVITY: Take a Tuscan cooking class! We took a traditional Tuscan cooking class with Chef Paolo Monti at his cooking school ($100/per person). We learned how to cook biscotti, veggie & meat raviolis, a traditional Lucca-style pasta sauce, roasted pork stuffed with herbs, a panzanella salad & more! The class includes one-on-one instruction, lunch (from the food you make), wine & biscotti to take home. IMG_5854 3
  • EAT: Osteria Da Rosolo We had the most amazing (and affordable) meal at this traditional Lucchese-style restaurant. Order the pappardelle w/wild boar sauce & the lasagna. And to end your meal, true Tuscan-style, order the Vin Santo (Italian dessert wine) with biscotti.IMG_6485 2
  • CULTURE: Take a walk to the top of the Delle Ore Tower for a stunning view of the entire city. The Guinigi Tower is also an option.



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  • We stayed: 1 night
  • The city has colorful buildings, narrow alleyways, a large piazza w/restaurants and shops
  • Larger than Lucca


  • ACTIVITY: Walk! We conquered most of Siena’s hotspots in a couple hours by-foot. We started by walking around the edges of the city and working our way inward. There are beautiful alleyways and stairways that provide vistas of the entire city.IMG_5313
  • EAT: Osteria La Chiacchera – this place was recommended by a couple people – we thought the food was traditional and affordable. It’s nice for tapa-style dining.
  • CULTURE: Visit the Palazzo Pubblico – This is the quintessential Italian piazza — with a tall clock tower. It’s a great spot for shopping for Tuscan ceramics and stopping for a quick espresso.




  • Wine region!
  • A short and beautiful drive from Siena
  • Wineries are well spread out and typically require a reservation before arrival
  • Very quiet area — not many restaurants or areas to stop


  • Visit a Winery & Take a Tour: We visited Avignonesi winery and took their tour. We enjoyed the tour because it gave us more of the history of the region and the winery — you also learn more about their speciality wines. Afterward, a tasting of 4 wines was included + a tasting of their olive oil.



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  • Stayed: 1 night (we stayed here as a pit stop after wine tasting in Montepulciano)
  • Very small and quiet town — especially in the Fall (we were here at the beginning of December) – we were only able to find one open restaurant on a weekday for dinner
  • Quaint town with shops and small brick alleyways
  • Stunning views that look like a Tuscan postcard
  • Give yourself 1-2 hours to walk through the town – you won’t need a full day here



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  • Stayed: 1 night
  • A quiet town, resting on the top of a hill with beautiful views
  • Very few spots were open for lunch in the Fall (early December)
  • Park inside the city — there aren’t many sidewalk options if you park just outside the city’s border


  1. Walk – another walkable city (once you are inside) — the city is also fairly small so you can cruise through the town pretty quickly. We walked for about 2 hours and then stopped for lunch. There are plenty of beautiful views since Montalcino is on top of a hill.
  2. EAT AND DRINK: Osteria Enoteca Osticcio – We stopped for lunch here. The restaurant has a beautiful view of the Tuscan landscape. The food was tasty too! We ordered a glass of the house wine from Montalcino.
  3. Visit a winery: Montalcino is another great area to try out different styles of Tuscan wines. There are plenty of wineries along the drive from Val d’Orcia — most, require reservation. We visited Castello Banfi — wow, what a beautiful stop and it really lives up to its name, ‘Castello’ (castle in Italian)! The staff was also very nice and knowledgable about wine.IMG_2009IMG_3404 2

Super Tuscan tasting



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  • Stayed: 1 night
  • A 2-hour drive from Montalcino with ocean views on the way to Pisa
  • We had to get back to Pisa the following afternoon for our flight so we decided to drive to Cecina to break up our final driving day — PLUS, living in Paris, we hadn’t seen the coast in weeks and the drive to Cecina was just what we needed!
  • A quiet beach town in the late-Fall — however, there was still several restaurants open
  • It was too cold to bask in the sun but we still enjoyed a leisurely walk along the sand, collecting seashells and rocks
  • EAT: EL FARO – we ate here, per our hotel’s recommendation (which we usually don’t take– we like to explore on our own but the town was quiet), and we were impressed! They have a nice 2-coursed menu that was reasonably priced and a great craft beer selection.



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  • We had a VERY quick (as in 2-hours before we needed to get to the airport quick) stop in Pisa on the way to drop off our rental car. We almost didn’t visit this cool town (lots of Italians didn’t have much good things to say about the city) but we were glad we stopped for a famous photo with the leaning tower of Pisa and a panini & espresso.
  • We would recommend staying a night in Pisa over staying in the beach town of Cecina, especially if you are visiting in late-Fall, winter. There is more to do in Pisa and more restaurant selections.



  • Be wary of electronic speed traps — there are signs that are posted on major highways that track your speed (the sign has a police man with his hand up)– if you’re caught speeding, expect a ticket in the mail
  • Renting a car is easy. Bring your driver’s license and passport. We played it safe and also bought the car insurance + snow chains. It’s better to be prepared!
  • Plan as you go when road tripping. We planned a general summary of places we wanted to see and also based some of our travel stops on appointments we had (i.e. the cooking school, winery visits) — BUT the rest of the time we planned as we went. I would look up hotels while Jeremy was driving –there are usually great deals on the day-of through the ‘Hotels Tonight’ app and Hotels.com. This also helped us determine places we wanted to visit longer — after visiting Montalcino we decided it would be a nice resting place while we learned that Val d’Orcia was too small to stay any longer than we needed to. Our rationale? These are things you won’t know until you get to the area — and if you already have a hotel booked for 2 nights there — you are stuck instead of exploring other areas.


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