Ultimate Guide for a Tuscany Road Trip (and just beyond)

This Tuscany Road Trip guide would take two to three weeks depending on how long you stay in each area. The following itinerary is what Mihaela of WorldTravelBug.com and I did, it is chock full of destination, hotel, restaurant and other recommendations. If you have any questions, feel free to leave a comment below.

Tuscany Road Trip view - Photo by Mike Shubic of MikesRoadTrip.com

Tuscany (Toscana in Italian) is a place romanticized in movies, immortalized by famous authors and artists, and, on the bucket list of many who dream of drinking wine and dining al fresco under a Tuscan sunset.

After spending three weeks road tripping around Tuscany, I can say for certain that this is a magical place that lives up to its reputation—and dare I say, surpassed my expectations.

Tuscany Road Trip Guide - Photo by Mike Shubic of MikesRoadTrip.com

Tuscany embodies everything that traveler’s look for in a vacation—deep history, romantic setting, rolling hills that kiss the horizon, world-class wine and so much more.

This Tuscany Road Trip Vehicle was an Alfa Romeo Giulietta

Tuscany Road Trip vehicle was the 2019 Alfa Romeo Giulietta

Decent car, but not much in way of power performance. It handled the curvy Tuscan roads quite nice though and it gets great gas millage.

Tuscany Road Trip Map screenshot

I booked the car online from Auto Europe and got a great deal for this three week Tuscany road trip. Auto Europe is an OTA (online travel agency), the vehicle itself was rented through Avis/Budget, which I would NOT recommend. At least not in Italy. When I returned the car three weeks later there were some minor scratches on the wheels in which they charged me over 1100 Euro. Thankfully, I booked the car with my World Elite MasterCard and they are dealing with the situation.

Tuscany Road Trip starts in Rome

Vatician Ceiling by MikesRoadTrip

Most everyone visiting Tuscany will fly into Rome or Florence depending on your departure city. If you fly into Rome, be prepared to wait a long time to pick up your rental car. I waited over three hours with Avis/Budget. Three hours! I’m not alone, after posting my frustration on social media; I learned this is common practice at this particular airport. It’s really inexcusable, but knowing this up-front might help you plan accordingly.

While in Rome we stayed really close to the entrance of Vatican City and spent most of our day there. I rented an Airbnb just a few hundred meters from the main gate of the Vatican and would highly recommend the space/unit.

I’m not going into detail on Rome as there is a lot of content on that city, plus, it’s not in Tuscany, the subject of this guide.

Next Stop Was to Civita di Bagnoregio

Civita di Bagnoregio aeria by Mike Shubic of MikesRoadTrip.com

Civita di Bagnoregio is located about 75 miles (or 120km) north of Rome and is just outside the borders of Tuscany. This remarkable hilltop village can only be accessed by a long and vertical ascending pedestrian bridge. No cars allowed. There is however a parking lot available at the end of the bridge.

While in Tuscany I visited many incredible hilltop villages, Civita di Bagnoregio is no exception when it comes to charm and intrigue. The town teeters atop a peak rising high above an enormous canyon. The earth that once connected Civita, to its bigger sister town, Bagnoregio, has eroded away over time, hence the reason for the footbridge—which is the only way in or out of the village.

Civita di Bagnoregio small square by MikesRoadTrip.com

If you’re staying in Civita di Bagnoregio, you can hire an ATV to bring your luggage into the village. When I was there it was 5 Euro per trip, which given the length and ascent of the bridge, is a bargain.

After the long walk across the bride, you’ll come to the main entrance, which is a large stone passageway cut by the Etruscans more than 2,500 years ago. The entrance is like passing through a portal into another world, one that dates back before Christ.

Tuscany Road Trip Guide Tuscany Road Trip Guide

While in Civita di Bagnoregio we stayed at a lovely B&B called Libera Mente Bed and Breakfast, the accommodations were not luxurious, but quite comfortable and full of charismatic charm. One window looked out to the massive valley below, while the other had a view of a small piazza. While “B&B” is in the name, they don’t actually serve breakfast, but rather provide you with a coupon for coffee, juice and a pastry at the restaurant below. [Note: In Italy, not much emphasis is placed on breakfast.]

 Libera Mente Bed and Breakfast collage by MikesRoadTrip.com

Don’t Miss

  • Osteria Al Forno is a pretty decent place for lunch or dinner.
  • We also had a couple uniquely flavored local beers at L’Arco, a nice little bistro for a sandwich, gelato or cold beverage.
  • There is an underground museum with lots of historic artifacts really worth checking out (only place in town, you can’t miss it).

 Museum in Civita di Bagnoregio by MikesRoadTrip.com


  • Il Pozzo dei Desideri is partially housed within an old Roman cistern (where we dinned), which was an interesting experience, but the food was not great.
  • En route to Montefollonico we stopped in the small village of Torrita Di Siena for lunch at Ristorante Piccolo, which offers some pretty stunning views, but just mediocre food.


Montefollonico, Italy

Montefollonico aerial photo by Mike Shubic of MikesRoadTrip.com

Montefollonico is a great little hilltop village with fantastic views of Tuscany. I highly recommend attending Cook in Tuscany, which is where we spent a week cooking with local chefs and sightseeing the region’s lesser-known Tuscan villages. Here are some of the highlights, whether you do them with Cook in Tuscany, or on your own. [Click the following link for a complete itinerary of our experience at Cook in Tuscany]

Don’t miss:

Cooking in Tuscany - Photo by Mike Shubic of MikesRoadTrip.com


Susanne at Cook in Tuscany - Cooking in Tuscany - photo by Mike Shubic of MikesRoadTrip.com

One of our cooking classes was at Netta’s Kitchen which was a great experience. Cortona has fantastic shopping options and the views of/from Santuario di Santa Margherita are amazing. BTW, this is where the famous book and movie “Under the Tuscan Sun” takes place.

Bagno Vignoni, Italy

Tuscany road trip to Bagno Vignoni in Tuscany Italy by MikesRoadTrip.com

This village is bit different from many others around Tuscany, instead of a main square; Bogno Vignoni has a massive thermal pond in the city center. The spring flows through town down a hillside into a series of pools in which you can go for a soak in the therapeutic waters. If you didn’t bring your swimsuit, you can take off your shoes, roll up your pants and soak your feet in the stream that flows through town before making its way over the edge of the hillside. These thermal waters have been used since antiquity. 

Pienza, Italy

Tuscany road trip to Pienza Tuscany by Mike Shubic of MikesRoadTrip.com

Named for Pope Pius II who was born here in the early 15th Century, this is a wonderful hilltop city to explore. The views are breathtaking and so too is the superb renaissance architecture.

Don’t Miss:

  • Dining at La Bandita Townhouse – wonderful outdoor patio and some excellent food.
  • Gelato at Buon Gusto – some of the best gelato in all of Italy with some really unique flavors, such as kiwi and spinach. Trust me, it works!
  • Andreucci Tenumenti is an outstanding 7th generation winery and one of the best overall tastings we had in this region of Tuscany. Watch my Cook in Tuscany video to see what an incredible place this is.

Flavio at Andreucci Tenumenti

Montepulciano, Italy

Tuscan wine and vinger cellar by MikesRoadTrip.com

This is another medieval hilltop town surrounded by vineyards and is known for its Nobile red wine. Here you’ll see artisans at work, with lost of wine bars and vinegar & olive oil shops. There are caves and tunnels under the town that were used to connect the grand palaces. Today, these tunnels are the perfect environment for aging wine and vinegar. Almost all wine shops in town have their slice of the underground.

Don’t miss:

  • Chiesa di San Biagio – Really cool church just outside of town.
  • Cantina Ercolani is one of the best underground cellars with free wine tastings.
  • La Dolche Vita is one of the best wine bars in town.

Montepulciano craftsman - Photo by: Mike Shubic of MikesRoadTrip.com

Monticchiello, Italy

Tuscany Road Trip view - Photo by Mike Shubic of MikesRoadTrip.com

During Etruscan and Roman times, this small village was a crossroads of streets, connecting several villages. You can still see the Cypress trees lining these old roads with traces of medieval fortresses.

Don’t miss:

  • Podere Il Casale is an agro tourism farm with cooking classes and a restaurant. They make their own cheese, pasta, have lots of animals on site, harvest honey and other amazing farm fresh stuff. This is a fantastic place that should be on your itinerary. The Tuscan views are pretty decent (actually stupendous) too.

Il Casale Azienda Biologic copy


Siena, Italy

Tuscany road trip to Siena Italy aerial by MikesRoadTrip.com

Siena has a very long history, dating back to the Etruscan times some 500 years B.C. The city saw most of its growth during the Middle-Ages. Today, its urban skyline is visible from the surrounding hills, which is rich in monuments, palaces and churches; it is one of the most beautiful cities in Tuscany and is much less crowded than Florence.

We stayed just outside of Siena at a typical Tuscan estate called Borgo Scopeto. This wonderful resort property is ensconced by vineyards and olive groves and boasts a spa, two swimming pools and a delightful restaurant. The road leading up to the hotel is lined with cypress trees, which sets the stage for an unforgettable experience that lay ahead. The lodging experience is exactly what you likely dream about when visiting Tuscany.

Borgo Scopeto aerial photo by MikesRoadTrip.com

Don’t Miss:

  • The historical city center of Sienna is a UNESCO world heritage.
  • Duomo di Siena and [Plaza] Piazza del Campo are main squares in Sienna where you will find lots of restaurants, grand architecture, street performers and more. Piazza del Campo is considered one of Europe’s greatest medieval squares.
  • Duomo of Siena is one of the most magnificent cathedrals in Tuscany with an incredible interior and massive mosaic floor.
  • Torre del Mangia may not be as famous as the leaning tower of Pisa, but it is the most recognizable landmark in Siena. The views from the top are magnificent, but you do have to climb 400 steps to see them.
  • Trivia: Scenes from the James Bond movie Quantum of Solace were filmed in Piazza del Campo.

Duomo of Siena by MikesRoadTrip.com

Pisa, Italy

TUSCANY road trip to the Leaning Tower of Pisa plaza by Mike Shubic of MikesRoadTrip.com

I’m sure that Pisa has a lot more to offer than just its leaning tower, but that’s all the time we had as we were heading to Cinque Terre. We were glad we stopped because the compound where the leaning tower of Pisa resides is not the only attraction. The Baptistery, Cathedral of Santa Maria Assunta and other structures are absolutely stunning. It is however very touristy, so be prepared for large crowds, especially during the summer months.


Cinque Terre (Riomaggiore)

Cinque Terre Italy - Photo by: Mike Shubic of MikesRoadTrip.com

Cinque Terre is a bit outside of Tuscany, but since we were so close, we had to visit for a few days. We stayed in Riomaggiore, which is the first of the five villages (from south to north). It did not disappointed…Cinque Terre is just remarkable and so much fun to explore. Plus, you get a heck of a lot of exercise walking up many flights of steps and inclines, which helped burn off a few of those Italian meals.

Monterosseo Cinque Terre aerial by Mike Shubic of MikesRoadTrip.com

Don’t Miss:

  • Take a boat tour to see the villages from the sea, which provides the best perspective. We took a sunset tour in a semi-private boat, which we would recommend. There is a large ferry-like vessel, but it is so crowed I’m not sure how much fun it would be.
  • Take the train to get from village to village. Since we were staying in the first village of Riomaggiore, we took the train to the last village (Monterosseo) and made our way back one village at a time. There is also a coastal trail, so you may want to walk to one of the villages, then use the train to get to your next stop.
  • We did 4 out of 5 villages and although it is quite difficult to choose, we thought that Vernazza was the most photogenic.
  • Torre Aurora in Monterosseo is an amazing place for lunch or dinner offering some extraordinary views.
  • Click the following link for live Cinque Terre weather forecast.

Monterosso al Mare in Cinque Terre by Mike Shubic of MikesRoadTrip.com

Tips When Visiting Cinque Terre

  • Don’t drive; it’s a pain to find parking.
  • Park your vehicle in La Spezia and take the train.
  • Pack just what you need and leave everything else in the car in La Spezia.
  • Check restaurant reviews before dining, lots of mediocre and overpriced food.

Continue Reading…

Click the following link for part two of this Road Trip of Tuscany.

Tuscany FAQ

  • How do I find the best place to stay in Tuscany?

    While you can find many wonderful hotels in Tuscany using a travel search engine like Travelocity, we have found that this particular region of the world is well served by Airbnb. You can stay in some really unique and high quality properties at affordable rates. If you prefer a hotel and know the area in which you want to stay, try using Google Maps to pull up the hotels in the area.

  • Do they speak English in Tuscany?

    In the larger cities that cater to tourists, speaking English is not a problem at all. In the smaller villages however, you may have a difficult time. If you are planning on visiting smaller villages, download Google Translate, this app will allow you to conduct a conversation with a non-English speaker.

  • Is it easy to drive in Tuscany?

    Yes, very easy. The roads are well maintained and generally easy to navigate. Beware of renting cars from Hertz or Avis/Budget without getting the insurance. If you drive away without insurance, and return the car with just the slightest scratch, they will charge you an arm-and-a-leg. Travel or insurance with your credit card will likely only cover the "damages," not all of the taxes and other fees they add on.

  • What currency do they use in Tuscany?

    All of Italy uses the Euro.

  • Is Tuscany Expensive?

    Depending on the time of year Tuscany can be on the expensive side if you visit the more popular areas. Tuscany is a massive region of Italy with many small villages that can be quite affordable.

Mike Shubic

Mike Shubic is a seasoned road trip travel video blogger, traversing the byways of the world looking for those hidden gems of the road. From unique destinations, unexpected discoveries, creative cuisine, intriguing inns to exciting attractions…the road is his page. The experiences are his ink. And every 300 miles, a new chapter begins. Whether you live vicariously or by example, Mike will do the exploring so you can have an adventure.


  1. What an incredible experience this sounds like. Definitely putting us on the bucket list .

  2. This really is one of those bucketlist items! I loved this trip and all the places we went to and experiences we had! I want to go back!

    1. It really was a lot of fun, and so amazing to do it with someone so special. Can’t wait to go back, but maybe next time in the spring. 😉

  3. What a great guide for Tuscany. Thank you so much, this is very helpful information. My wife and I are planning a trip there next year.

  4. What a fantastic guide to Tuscany. This sounds like an incredible trip! Thanks for all of your work.

  5. This sounds like an incredible trip. Thanks for the information.

  6. Wow, this sounds like such an amazing trip. I would love to do this one day. Thank you for letting me live vicariously through your experiences.

  7. Mike this post is amazing. This really is one of those bucket list places! I loved this trip and all the places you featured! Thanks for providing this information.

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