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 in Montecatini Terma. 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.
Read about Florence and Tuscany
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 city on the Serchio river in Italy’s Tuscany region. It’s renowned for the well-preserved Renaissance walls encircling its historic city center and its cobblestone streets.
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.
Montecarlo di Lucca
Montecarlo di Lucca is a hill town in the Province of Lucca in the Italian region Tuscany.
Montecatini Alto
Montecatini Alto is a hill town located above 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.
Siena
Siena, a large and beautiful city in Italy’s central Tuscany, is distinguished by its medieval brick buildings.
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 here.
Montepulciano
Montepulciano is a medieval and Renaissance hill town located in southern Tuscany.
Florence
Florence, the capital of Italy’s Tuscany region and birthplace of the Renaissance, is home to masterpieces of art and architecture.
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.
Planning a Trip to Tuscany
Find a hotel in Tuscany
- Booking.com – Find a place to stay in Florence.
Get the best price on a flight to Florence
- Skyscanner – Find the most affordable flight to Tuscany on a search engine you can trust.
Rent a car in Tuscany
- Auto Europe – This site offers the best auto rates in Europe.
Take a tour of Tuscany
- Tour Tuscany – Book a tour on Viator to see the amazing sites of Tuscany.
- Tours by Locals – Find a local guide to take you on a private and personalized tour.
Don’t forget to buy travel insurance!
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Hi Rebecca! Your photos are wonderful. We visited Tuscany several years ago and LOVED Sienna and Montepulciano! Such an amazing country. Of course we were there in the fall so it was warmer so coats weren’t necessary. But you brought back a lot of great memories AND some encouragement to visit some of the other cities you mentioned. Thank you! ~Kathy
Thanks Kathy,
I wish we could have been there in October during the grape harvest and full on truffle season but actually November and December was pretty comfortable. So glad you were able to see Siena and Montepulciano. I agree, they were both amazing! There are so many wonderful little towns to visit. I can’t wait to go back.
Isn’t Italy delicious? Thanks so much for sharing your pictures. They brought back good memories!
Thanks Laura,
Yes, Italy is delicious in many ways besides just the food. Glad to tweak some memories for you.
Our son studied in Florence his Junior year at UCLA. We had a ball discovering Italy through the eyes of a resident. I loved your photos. The architecture of Tuscany is so magical, isn’t it?
I bet that was so much fun! My boyfriend’s daughter studied in Florence with Chapman University as well and he visited when she was there but that was before we lived together. I wish I’d had more time in Florence. Cruise ship excursions are way too quick.