Touring Tuscany: From Grand Cities to Rustic Hill Towns

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We spent 3 weeks touring Tuscany in November/December. It’s a magnificent region where you can visit mysterious medieval cities and tiny Etruscan hill towns. All are located within driving distance. The food, the wine, and the magnificent views make it hard to ever leave.

We took a train from Rome to Florence and headed off to stay for a few days at the Ercolini E Savi Hotel in Montecatini Terma.

Check current prices at Ercolini E Savi Hotel here.

It’s a spa town located in the heart of Northern Tuscany between Florence and Pisa. While we were there we went to one of their famous mineral spas. We also visited several old cities and hill towns including Lucca, Montecarlo di Lucca, and Montecatini Alto. Then we drove South to Siena stopping at Castellini in Chianti and Montepulciano.

We spent 2 nights in Siena, which was magnificent, and then drove to Sorrento where we stayed for five nights. We booked a private tour that took us on a day trip through the Amalfi Coast and Pompei.

We then headed back to Rome to board the Cunard Queen Elizabeth at the ancient port of Civitavecchia. Our first port was Livorno back in Tuscany where we boarded an excursion bus that took us on a too-quick tour of Florence and Pisa.

Tuscany is an amazing place to visit and I especially loved exploring the hill towns. We were traveling during winter so most of the towns were quiet and relaxed with almost no tourists. There’s nothing better than sitting on top of a beautiful hill overlooking vast vineyards, sipping a glass of Chianti and nibbling on freshly baked bread dipped in truffle oil.

To read more in-depth about our adventures in Italy click on the following articles:

• What I Learned About Eating in Italy
• My Foodie Vacation in Italy Continues to Tuscany
• Our Italian Itinerary and Recommendations
• First Days in Rome Foodie Heaven
• Collecting Doors and Travel Memories

Scroll down to see my photo galleries of the cities and hill towns we visited in Tuscany.

Lucca

Lucca is a medieval city on the Serchio river in Italy’s Tuscany region not far from Pisa. It’s renowned for the well-preserved Renaissance walls encircling its historic city center and its cobblestone streets. We climbed to the top of the Guinigi Tower where you can get a sweeping view of the entire area. 

The city is Etruscan in origin but during the Roman era, it served as a meeting place for Ceasar and Crassus. It’s known as the city of 100 churches. You can take a bike ride through the city and its walls, enjoy a variety of restaurants, museums, and enjoy gelato on the square.

Click on the thumbnails in the photo galleries below to view them FULL SIZE. Please feel free to share any photos you like on social media.

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Montecarlo di Lucca

Montecarlo di Lucca is a medieval hill town in the Province of Lucca in the Italian region Tuscany on top of the hill of Cerruglio. After the Pisan occupation ended in 1333 it took on the name Monte Carlo in honor of the future emperor who had helped Lucca get rid of the Pisans.

It was once the site of the ancient castle of Viviana. Looking down from the hill you see a landscape filled with olive trees and rich vineyards that produce some of the finest wine in the world.

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Montecatini Alto

Montecatini Alto is another medieval hill town that overlooks Montecatini Terma in the eastern end of northern Tuscany between Florence and Pisa. During high season, you can take a funicular up to the old city.

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Siena

Siena is located in central Tuscany and is known as the “city of art.” The old city is protected by walls and is surrounded by a field of olive trees and vineyards. It started as a Roman colony.

During the middle ages, it was a rival of Florence and endured fierce fighting and devastation from civil wars and plagues. It reached its height of power during the 11th century and arts and culture began to flourish.

The large Piazza del Campo is the central gathering and eating place surrounded by famous buildings like the Palazzo Pubblico with its Tower of Mangia. The magnificent Duomo, that stands out with it’s black and white striped marble rises above it. It’s one of the most incredible cathedrals in all of Europe.

The streets are made of bricks and stones and it hasn’t changed much from medieval times. Art museums, the Academy of Music, and other architectural wonders are everywhere you look.

It’s a city of college students and I felt safe walking through it even at night. During the winter, at least, when we were there, I didn’t see any hustlers as you do in tourist-laden Italian cities.

One of its most famous events is the Palio of the Contrade di Siena that began as early as 1310. It is a feast to honor the Blessed Virgin where costumed horse riders compete for the painted silk drape. The race is followed by a parade of participants in elegant costumes with drums and flag-waving. The Palio takes place twice a year on July 2 and August 16.

We stayed at the Hotel Italia Siena, a small and charming boutique hotel, which is conveniently located right outside the Camollia Gate.

Check current prices at Hotel Italia Siena here.

I would love to go back there by myself to spend time wandering the streets at a slow pace to take in all the art and beauty.

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Castellina in Chianti

Castellina in Chianti is a hill town near Siena. The city’s origins go back to Etruscan times and many artifacts from that time period can be found there. The Archaeological Museum of the Sienese Chianti was founded in 2006 after an excavation unearthed the Etruscan burial mound of Montecalvario.

It’s worth checking out if you come to this village. It was the furthest stronghold of the Florentine Republic but was seized and destroyed by the Visconte of Milan in 1397. In 1478, after the damage had been repaired, it surrendered to the Sienese and Neopolitan troops. As punishment, the fortress was burned.

In the mid-1920s, the fortress was restored and bought by the city of Castellina.

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Montepulciano

Montepulciano is a hill town village located in southern Tuscany on the border of Umbria that is Etruscan in origin. It was strategically located along the most important paths of commerce during medieval times. The village has been remarkably preserved and plays host to a wide range of cultural and religious events.

It’s also known for its wine, food & crafts products. We enjoyed lunch at the Art Noveau-style Caffe Poliziano, established in 1868. It sits in the historical center of Montepulciano overlooking the Valdichiana from the balcony.

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Florence

Florence, the capital of Italy’s Tuscany region and the birthplace of the Renaissance, is home to masterpieces of art and architecture.

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Pisa

Pisa is a city of 89,523 residents but is best known for it’s Square of Miracles consisting of the Cathedral, Baptistery, and the Bell Tower – Leaning Tower of Pisa. Both the Cathedral and Baptistery are beautiful and hold priceless artwork and artifacts.

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Check out top things to do in the area here.

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