Jenna, Lyndsey, Nicole & Kristen find plenty of things to do in Tuscany on their relaxing girls trip – complete with plenty of wine and pizza!
Agriturismo Terre Di Nano in Pienza
Activities
Cannot recommend Terre di Nano enough! Staying here was our favorite activity of all the things to do in Tuscany! This gorgeous estate is working winery where you can stay for a few days. We loved lounging outside, reading a book, and drinking a glass of wine while soaking in the amazing view. We were a group of 4 girls, but this would be amazing as a romantic trip for a couple. They have a pool, bicycles, a bocce ball court, and also offer a few activities listed below:
Cooking class
One of the popular things to do in Tuscany is a cooking class, and this was by far a highlight of our trip! Christina taught us how to cook homemade gnocchi, tomato sauce, and tiramisu, and it was all amazing. We had a huge lunch, and then got to take the leftovers back to our room to heat up again for dinner. She was a great teacher, and we were able to write down all the recipes at the end so we could go home and recreate them.
Winery tour
We also got a chance to tour their wine cellars, learn about their wine making, and do a wine tasting. We enjoyed it and bought several bottles of wine to fly back to the States with. Naturally, wine tastings are one of the best things to do in Tuscany!
La dolce vita!
Restaurants
Since the estate is out in the country, there really aren’t any options of places to go eat. They do have a small restaurant on-site. We stopped by a grocery store on our way there the first day and brought meats, cheeses, and breads for meals. We also had our leftovers from our cooking class another night. You can choose to pay extra to have breakfast included with your room as well.
Hotel
Since there were 4 of us, we rented the Bellavista apartment. It was 2 bedrooms, 2 bathrooms, and was very spacious with a nice kitchen. They also have 2-person rooms, with no kitchen, and larger 4-8 person houses.
Transportation
Terre Di Nano is located in the Provence of Siena. We took the train from Florence to the Chiusi station and they sent a driver to pick us up there. It was about a 15 minute drive. The estate is not close enough to walk anywhere, but you can arrange transportation through them to get a driver to drive you to Pienza or Montepulciano, which are both about 15 minutes away.
Castiglion Fiorentino
This small, walled, former medieval city is in the province of Arezzo, between the cities of Arezzo and Cortona. Its quaint feel, narrow cobblestone streets, friendly people, and lack of tourists make for a wonderful day trip or overnight stay. It’s located right on the main train route from Florence to Rome, so it’s even an easy middle point to stay several nights and do day trips within Tuscany. There are so many things to do in Tuscany within a few hours from here.
Activities
Agriturismo La Pievuccia
La Pievuccia is a beautiful organic farm and working winery. We went for a wine tour, tasting, and olive oil tasting and it was fabulous. Make a reservation ahead of time because they only do tastings on select days/times. It was about a 30 minute walk for us to walk there; it’s outside of the city.
They also have beautiful apartments to stay overnight, accommodating 2-6 people. For those staying overnight, they have a restaurant onsite that serves breakfast and dinner, for a fee. They have a pool and working garden. It looked fabulous to stay overnight there, but it didn’t work out for us to stay on this trip. I’m sure if you’re staying overnight you can arrange a pick-up with them in town, so you don’t have to walk with your luggage.
Archeological Museum and Public Library
Castiglion Fiorentino was founded by the Etruscans around 500 B.C. and is known as an Etruscan archeological site. The Archeological Museum showcases many of those artifacts. The Library was cool because there was a room at the top with shelves and shelves of old books. They were written in the 13th, 14th, 15th centuries. These books were not written on paper, but instead were on sheepskin (like a very thick piece of paper) and handwritten by monks. The museum and library are located at the top of the hill in the center of town.
Corso Italia
Corso Italia is the main street through the center of the walled part of the city. It has interesting little shops to wander through. We stopped in at a wine shop on the corso for a wine and cheese tasting.
Restaurants
Roggi’s
Roggi’s was a favorite spot and the pizza was amazing. True Italian thin crust pizza! It was filled with mainly locals, and located in the center of the city, just off the main corso.
Velvet Underground/Garden Underground
Velvet Underground and Garden Underground are bars are owned by the same people and each only open half the year. Garden Underground is the outdoor bar, open during the summer and closing early October. Velvet Underground is indoor, open in the fall and winter. Both are great bars – filled with locals and often have live music. Garden is located on Via Trento, just down the street from the main entrance to the walled part of the city. Velvet is in the center of the city, off the main corso, just around the corner from Roggi’s (above).
Hotel
Viziottavo Bed & Breakfast
We were very happy with our stay at Viziottavo Bed & Breakfast. It opened in 2011, so it’s fairly new. The rooms are nice, and it’s located on top of the hill in the center of town. Included in your stay is a nice breakfast of pastries, yogurt, fruit and cheese. I had a wonderful cappuccino made for me each morning. It’s about a 15 minute walk from the train station, but they offered to pick us up and drop us off, so that was nice.
Transportation
Everything within Castiglion Fiorentino is walkable. It’s located right on the main train line, so it’s easy to take a train straight there from both Florence and Rome. There are so many things to do in Tuscany within an hour or so train ride from here. Tip: Note that only Regional trains stop at that train stop. (These are the slower trains that make more stops in the smaller cities.) If you take a bigger express train, it will stop in Arezzo, the neighboring city, where you will then switch to a smaller regional train for 1 stop to get there. There is also a public bus system that you can take to get between the neighboring cities.
Day Trip: Cortona
This charming town is located in the province of Arezzo. The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill with spectacular views of the countryside. We spent an afternoon here, wandering through the shops filled with foods, handmade items, and art. There are a few wine bars, and we enjoyed lunch with an amazing view. This is also where Under the Tuscan Sun writer Frances Mayes bought her villa, though there isn’t anything to see regarding the book or movie.
Take a regional train to the Camucia Cortona stop. (It’s 1 stop south of Castiglion Fiorentino, written about above.) This lets you off at the bottom of the hill, so you’ll need to take a bus from there to the top of the hill. You can walk, but it’s about 2km of incline.
Day Trip: Perugia
This is another walled medieval city, located in the Umbria region. We traveled there for the day to visit the Perugina Chocolate Factory, home of the famous Italian Baci chocolates. We went on the tour of the factory to see the production, and then walked through the museum at the end. Yes, there are free Baci samples! Call ahead to book an English speaking tour. All the displays in the museum are only in Italian, but you’ll get the idea. This was another one of our favorite things to do in Tuscany!
You can take a regional train to Perugia. Then you’ll have to take a bus from the train station to get to the factory. It’s about 20 minutes from the center of the city.
Hundreds of chocolates!
Day Trip: Pisa
The Leaning Tower of Pisa is probably the most over-hyped, and one of the most popular things to do in Tuscany! Everyone knows the leaning tower of Pisa. It’s a freestanding bell tower, built on an uneven foundation, causing it to tilt over time. It’s cool to see, and take funny pictures with. You can buy a ticket to climb the stairs to the top and there are great views of the city. Also located next to the tower are the Pisa Cathedral, Baptistry and a museum.
Pisa is about a 2 hour train ride from parts of Tuscany. It’s better to stop through here if you’ll be in Florence, flying out of the Pisa airport, or going elsewhere in Italy. You’ll have to take a bus to get from the Pisa Centrale train station to the tower. It’s only about a 15 minute bus ride, or about a 2km, or 40 minute, walk. We were just in Pisa for a few hours, passing through, and I wouldn’t plan much more time than that there.
Things to Do in Tuscany – Italy Travel Tips:
Trains – You can take the train pretty much everywhere, so don’t be scared to use them. There are so many things to do in Tuscany that are only a quick train ride away! However, don’t forget to validate your train ticket! You’ll buy a general train ticket from one city to another, but you must stamp it with the date and time in order for it to be valid. If you get on the train without validating, and the conductor comes through to check, you could get fined. Look for little boxes on the train platforms near where you get on the trains to punch your ticket.
Siesta – In the small towns, many of the shops and cafes close for a few hours early afternoon so everyone can go home and rest, called siesta, or riposo. The timing varies from business to business, but usually lasts about 1 ½ hours to 2 hours. It may begin anywhere from noon and 1:30pm and run until anywhere from 2:30 to 4pm. Plan around this, so you’re not arriving just as everything is closing.
Other travel guides you might like:
Rome, Tuscany, Naples & Sicily, Italy – 2 Weeks in Italy: Rome, Tuscany, Naples & Sicily
Cinque Terre & Rome, Italy – Rome to Cinque Terre: Hikes, History & Pasta
Paris, France – 3 Days in Paris: Experience Paris City Life
London, England – The Ultimate 5 Day London Itinerary
Oia, Santorini, Greece – Guide to Oia: Where to Stay in Santorini
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