Tuscany Road Trip, A Trip that Will Inspire

A Tuscany road trip was always one of our dream vacations. Driving through the green landscapes, enjoying the food and wine, and learning about the history and architecture of cities like Florence and Siena or get lost in the beautiful towns. It was a trip we simply had to take at some point. And this summer luck was on our side! On a trip to Madrid for a presentation by Booking.com, there was a contest and Abby won first prize: a trip where ever we wanted in Europe with the hotels and airfare paid by Booking! It was time to visit Tuscany!

Tuscany Road Trip

Florence, our first stop in Tuscany

As we planned our trip, Booking.com helped us by making our hotel reservations at the places we chose and finding our flights. The first flight was with Swiss Airlines and left Malaga with a layover in Zurich, putting us in Florence at 7pm. It was our first stop, an obvious choice with it’s architecture, history, gastronomy and cobblestone streets. There is so much to see in Florence, and the two days we spent weren’t enough, but we did try to take advantage of the time we had!

Follow us through Tuscany!

We decided to take a tour with Walks of Italy to see the architecture of Florence and better understand the significance of some of the great works of art in the city. What impressed me most, more than I expected, was seeing David close up. There was so much definition in the details. We were really glad that we took the tour and our guide, Teresa, was able to show us the important sights in a friendly and fun way. The rest of our time in Florence was spent wandering the streets and tasting our first bites of delicious Tuscan cuisine.

The pose of Michelangelo's David in Florence

The Tuscany Road Trip Begins

Azzienda Il Palagio, Panzano en Chianti

We couldn’t wait to drive through the green fields of Chianti, and our first stop on our road trip through Tuscany was a wine tasting. We were heading to the Azzienda Agricola II Palagio in Panzano in Chianti. There Gioia, a wonderful woman who was going to show us the vineyard and explain everything about the wines and the ecological products, was waiting for us. The best part was the story of how her family had started the vineyard, everything was very personal. Of course we tried the wines that they had to offer, along with some local cheese (tears come to my eyes when I remember the moment!). In Chianti we also saw other towns including Panzano and Greve, all full of light and color that left us wanting to continue exploring on our trip!

Monteriggioni, Tuscany

Everyone had told us that Monteriggioni was a gorgeous town that we just had to visit! At first we were surprised to see a medieval city with it’s wall completely preserved in such excellent condition. When we went inside we were expecting a city where we would see people living in medieval surroundings in the 21st century. We were a bit disappointed to see that it was geared towards tourism and didn’t have the atmosphere that we were hoping to see. Although as an historic monument it is very impressive and worth a visit!

Siena, Tuscany

In Siena we spent the first night of our Tuscany road trip. Lorenzo, who had started a B&B in the house where he grew up, took great care of us! Siena was a surprising city full of little cobblestone streets that you didn’t know they might lead. The views from on top of the would be door to the cathedral are absolutely amazing (almost better than the Torre del Mangia). And the whole cathedral was black and white!

Colle di Val dElsa, Tuscany

Before we headed to San Gimignano from Siena, we made a quick stop in Colle di Val d’Elsa. An unexpected stop that was just at the top of a hill. However, if there is one benefit to taking a Tuscany road trip, it is finding towns like this one, from another century that seem to be untouched by tourism. Take a walk through the streets of these towns, that’s all you have to do to enjoy.

San Gimignano, Tuscany

Gelateria Dondoli, San Gimignano

We finally arrived in San Gimignano, which everyone had told us was beautiful. They were right because even though the town was full of tourists, it still has some of the authenticity that makes you feel like you are back in medieval times. Apart from walking around the town, check out the Museum of Torture where they show numerous real artifacts and explanations of how these devices were used. At night, just before we left, we enjoyed a concert in the main plaza while enjoying a lemon and white wine gelato from the Gelateria Dondoli, winners of the best ice cream in the world! (Not a bad end to our day!)

Volterra, Tuscany

Volterra was one of the towns on our road trip through Tuscany that we enjoyed the most. We would have stayed longer had we known, because it captured our hearts right away! The buildings, streets, hills, roman theater, etruscan ruins and the food! (The crostinis and wine at a little bar called Sapore di Toscana! were delicious! Send some to Málaga if you are reading this!)

Livorno, Tuscany

We stopped in Livorno because we wanted to include a stop along the Tuscan coast. Although there are some interesting places including the board walk and the Venetian Neighborhood, it reminded me of Málaga before it was renovated into the beautiful city that it is today.

Tower of Pisa, Tuscany

Near Livorno was our stop for that night: Pisa. This city surprised us in the best way because people had told us that all it had was the tower. It is a nice city to walk around with churches and buildings from the past. Also, this was the place where we tried the best ice cream we’d ever had in our lives. The lemon and the coffee ice cream from Gelateria De’ Cotelli (I would go back to this city just for the ice cream!)

Lucca, Tuscany

From Pisa to Lucca is only about 20 minutes by car, but the contrast between the cities is huge. It was in Lucca that we met Paolo in a small restaurant where we had a delicious lunch (La Tana del Boia). Paolo personallly contacted a friend of his who had a bodega in Montecarlo (on the way to Florence). Thats how, after visiting the Puccini Museum in Lucca, we continued our route according to Paolo’s directions.

Pedro and Abby in Tuscany

La Tenuta del Buonamico in Montecarlo gave us a tour and we tried some of their wines (the sparkling wines were fantastic!) Our route took us back to Florence where we would spend the night in order to catch our flight to Málaga the next morning. It was an amazing trip, full of wonderful memories, romance and delicious food and wine. A trip that we’ll remember all our lives. We don’t think a  “ruskommendation” is necessary; but if you go, make sure to take your time and do a Tuscany road trip

Having Wine in Tuscany

Where to stay in Tuscany: The hotels we chose

Five Roses B&B, Pisa

  • Palazzo Graziani, Florencia. A historic palace with impressive views, about 10 minutes’ walk away from the Duomo. A comfortable, relaxed place where we were treated to 5 star service. We ruskommend it with 5 boquerones.
  • Ai Canapi, Siena. A B&B enthusiastically run by Lorenzo and his girlfriend. (In fact, it was Lorenzo’s old home and we slept in his childhood bedroom.) Needless to say, we were treated with the utmost care. The only downside is that it’s 20 minutes’ walk from the historic center, but parking is easy and the neighborhood was peaceful with plenty of restaurants. We ruskommend it with 5 boquerones.
  • Five Roses, Pisa. Another B&B, this time run by a charming lady who literally made us feel like she was our mother who had invited us to her house! She prepared 5 different pastries and cakes for breakfast and all sorts of things for the buffet. The bedroom was charming and the service was amazing. It’s 20 minutes from the historic center, but once again parking is easy. We ruskommend it with 5 boquerones.

Where to eat in Tuscany: The restaurants we tried and ruskommend

Crostinis and wine in Sapori de Toscana, Volterra

  • Alimentari Uffizi, Florencia (a small deli with cold cuts and cured meats from the family farm).
  • Osteria del Buon Governo, Siena (Delicious gnocchi!).
  • Trattoria da Giacco, San Gimignano (to enjoy a beautiful sunset in the town).
  • Sapori di Toscana, Volterra (a charming place with crostinis and wine from the area).
  • Ristorante Galileo, Pisa (their specialty is pasta with fish and shell fish).
  • La Tana del Boia, Lucca (their specialty is sandwiches and cured meats).


Ristorante Galileo, Pisa

Ice Cream Shops and Cafés that we ruskommend

Caffè Brunellesco, Florence


  • Caffè Brunellesco, Florencia (for breakfast in Florence).
  • Caffè Gilli, Florencia (to have a drink with views of the Piazza de la República).
  • Caffè Rivoire, Florencia (excellent coffee).
  • Gelateria Perché No, Florencia (delicious ice cream).
  • Gelateria Dondoli, San Gimignano (Crema de Santa Fina was voted the best flavor in Tuscany 2015 and they were awarded the title of Best Ice Cream in the World in 2006, 2007, 2008, and 2009).
  • Gelateria De’ Cotelli, Pisa y Lucca (the best ice cream we’ve ever tried!).
  • Pasticceria Barone, Colle di Val d’Elsa (excellent canolis and ice creams).

Gelato in Tuscany

Canolis in Colle di Vals d'Elsa, Tuscany

Vineyards we visited in Tuscany

Grapes from Tuscany

Il Palagio, Panzano en Chianti

  • Azienda Agricola Il Palagio, Panzano en Chianti (Ecological).
  • Tenuta del Buonamico, Montecarlo (just outside Lucca).


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Pedro Ramirez
I was born and raised in Málaga, Spain. After living in Madrid, Barcelona and New York, I've returned home to enjoy the sun! I love to share the places I discover and write about them.
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