You’ve heard of the wonderful things to do when vacationing in Tuscany, but where is Tuscany?

The region of Tuscany, according to is made up of 10 provinces: Florence, Arezzo, Grosseto, Livorno, Lucca, Massa Carrara, Pisa, Pistoia, Prato, and Siena. The capital is Florence and in Italian, Tuscany is Toscana.

A first timer to the region will find it challenging to choose where to visit and what to do just like Trippy users, Ann Dawson and Andreas Rossi.

Ann asked:

What to do in Tuscany
In Italy: We are a group of 5 women who have rented a villa on the outskirts of Siena in Italy for 10 days. What are some of the best places in the area to visit and what recommendations do you have for transportation?

And here’s Andreas’ question:

Which towns in Tuscany should we see?
My fiancee and I are renting a small apartment in Florence this summer, and we’d like to take a few day trips outside the city, but we’re not sure where to go. A friend has recommended Siena, but that’s the only one on our list. Does anyone have any other suggestions?

To start a tour of Tuscany, most people fly into Florence or Pisa. Or cruise to Livorna and arrive by Trenitalia trains. And if you’re like Ann wondering what to do in Tuscany, here are ideas given by locals and travelers that have been to the region.

1. Spend time in Siena

Don’t miss Siena when visiting Tuscany. Matthew Coccoluto from Boston wrote:

Siena is an excellent location to check out, especially the main square. If you are there on either July 2nd or August 16th, then you may want to look into checking out the Palio, a horse race around the main square where a rider represents each of the cities neighborhoods. It is a very unique and special event followed by massive celebrations, especially for the winning neighborhood. I don’t want to compare it to say Carnival in Rio, but it is one of those unique to location events, that people from around the world check out.

Some of the top attractions in Siena are:

  • Siena Cathedral
  • Mangia Tower
  • Santa Maria della Scala cultural center and museum (was the oldest European hospitals)
  • Piazza del Campo
  • Orto de’ Pecci (an urban oasis with gardens and a restaurant)

2. Visit Cortona

Matthew Holmes suggested Cortona:

One of my favorite Tuscan towns is Cortona. It is just the right size to maintain its charm and still have a few good options for drinks, dinner and meandering up winding alleys or through shops. Cortona is perched on top of one of Tuscany’s famous hills giving it views from almost every point. Also, there is a nice park that runs along a ridge that is very relaxing to take a stroll in; it even has an outdoor theater connected to it. The main shopping road is Via Nazionale, and if you happen to be there on a Saturday, there is a market in Piazza Signorelli.

When in Cortona visit:

  • Museum of Peasant Culture in Fratticciola
  • Girifalco Castle
  • MAEC, the Etruscan Academy Museum

3. Drive through Crete Senesi

Besides the cathedrals, castles, and piazzas in towns and cities, Tuscany also boasts of the awe-inspiring landscape filled with cypress trees, rolling hills, farms, wineries, and medieval villages. One must take a drive to admire the view of the Crete Senesi says Trippy user Roni Kennison. She said:

I would recommend renting a car and exploring small towns and wineries. I would also say to drive through the Crete region. There are incredibly beautiful landscapes just outside Siena that often go missed. I also love the Tuscan coast. The town of Castiglione Della Pescaia is just 1 hour 15 mins from Siena with a great old town and beautiful beaches. In the region of Maremma, there are many incredible towns like Pitigliano that are truly incredible. In addition, there are several hot spring spas near Siena that are also very beautiful, like San Casciano dei Bagni or Rapolano Terme.

Places to check out:

  • Buonconvento – a medieval village
  • San Giovanni d’Asso Truffle Museum
  • Asciano – stunning architecture and art

4. Explore the art and architecture in Florence

Even if you’ve been to Florence more than once, this world-famous Renaissance city is still worth a visit again and again if you like art and architecture, because as Tiffany Weber, a Trippy user pointed out:

You could easily spend a week there and probably still not have thoroughly done/seen everything especially if you enjoy art. The museums are amazing. Do walk to the other side of the river and see the view from Piazzale Michelangelo and stop to eat at Borgo Antico.

You’ll also want to check out:

  • Michelangelo’s David
  • Uffizi Galleries
  • Ponte Vecchio
  • Florence Baptistery

5. Stop by the Leaning Tower of Pisa

Pisa is only an hour train ride from Florence. Most people head over there for a half day trip to check out the Leaning Tower of Pisa. Trippy user, Tiffany Weber said there is more to Pisa than just the tower:

There is more than the Leaning Tower of Pisa – the neighboring church is truly gorgeous. Take the time to see it all and then head to Pisa’s beach at Marina Di Pisa, a very tiny town that is essentially a strip of land, one road along the water full of restaurants. It’s a beautiful, peaceful place for dinner and to watch the sunset. If you get there between dining hours (Italians eat lunch closer to 2-5 and then dinner 9-, so the American dinner hour is closed.), there’s an excellent focaccia shop here that’s easy to find.

6. Wine tasting in Tuscany

Caterina Pomini, a Florentine knows where to go for wine tasting. She recommended the following picturesque and famous wineries:

1) Antinori nel Chianti Classico (Cantina Antinori) – It is located in San Casciano in Val di Pesa (exactly in Bargino) – approximately 30 minutes from Florence.

2) Petra (Cantina Petra) – Suvereto (province of Livorno) – a way to discover a “non-touristy area” near the Etruscan coast.

3) Castello Banfi Enoteca (Castello Banfi) – Montalcino (province of Siena) much more traditional

4) Tenuta Rocca di Montemassi (Rocca di Montemassi) – Roccastrada (province of Grosseto)- a way to get a glimpse of Maremma (the wildest part of Tuscany).

5) Rocca di Frassinello (Tenuta Rocca di Frassinello) – Gavorrano (province of Grosseto), in Maremma.

6) Castello di Brolio (Brolio Castle) – approximately 8 km from Gaiole in Chianti.

There is also a couple of wineries you can easily reach from Florence ( both located in Greve In Chianti.)

  • Montefioralle Winery (Azienda Montefioralle)
  • Castello di Verrazzano(Castello di Verrazzano)

She concluded:

I would like to end by saying that it all depends on your tastes… think about the places you would want to visit and then choose the nearest winery.

7. Go off the beaten track to the medieval village of Castiglion Fiorentino

Trippy user Michael Hennes from San Diego suggested off the beaten track destinations and wineries. He wrote:

There are so many places, if you want to get off the beaten path then head to Castiglion Fiorentino. You can get there on the train from Florence, Rome or Venice. Nobody knows about this medieval village, it is off the beaten tourist path, with some amazing local wineries and places to stay from small hotels to B&Bs or rent a farmhouse at a local vineyard.

When in Castiglion Fiorentino check out:

  • Collegiate Church of Santi Michel e Guiliano
  • The Franssineto Farm Estate
  • Civic Pinacoteca

8. Rent a bicycle in Lucca and cycle through the heart of Tuscany

Tiffany Weber highly recommends Lucca.

Tiffany wrote:

One of my favorite cities is Lucca. It’s surrounded by the old city wall which is a great place to walk or rent a bicycle and ride. Such a darling town, it’s truly beautiful inside and fun to walk through.

Per, you can cycle along Via Francigena, the ancient trade route, from Lucca to Siena, passing by Tuscan medieval villages like Monteriggioni and San Gimignano.

9. Take a trip to Fiesole for a bird’s eye view of Florence

Just a half hour drive away is Fiesole, a town with cypress-lined streets, gardens, ancient ruins and a viewpoint to get the best views of Florence. But there’s more to discover if you take the time to stroll through the Fiesole. A Trippy user, Carina Chiodo from San Francisco wrote:

With stunning, grapevine-embellished views of Tuscany’s panorama, this quiet hilltop getaway is like a breath of fresh air from the sometimes-chaotic city. There is nothing flabbergasting or high-energy about Fiesole, just breathtaking views in a relaxing, authentic Italian neighborhood. They have a Saturday farmer’s market with very memorable meats and cheeses- I still reminisce about feasting on hunks of freshly-baked ciabatta wrapped in torn up strips of fresh buffalo mozzarella as a picnic lunch. I would recommend getting a picnic and taking a scenic walk up the cobblestone Via Belvedere- it leads to the highest peak of Fiesole where you will take in views heavily laden with olives groves and a gorgeous Tuscan sky as the backdrop.

10. Stay in a Tuscan villa

Tina Cataldi from Livorno runs an agriturismo (bed and breakfast farmhouse) in Tuscany:

I am running an agriturismo near Volterra, it is called Agriturismo Fattoria di Statiano, and we produce wine in Micciano. We would love to have you at the farm! But mostly, I recommend visiting this part of Tuscany that is off the beaten tracks, really and authentic spot! Nearby there is the stunning little village on the top of rolling hills like for example Montegemoli and Querceto.

There are 4,500 agriturismo accommodations in Tuscany that cater to different budgets and interests. Check it out on

Going to Tuscany anytime soon? Get your questions answered. Become a Trippy user now.

Photo credit: Pixabay

Mentioned in this post
  1. Siena
    Metro Area in SI Italy

    SI Italy
  2. Cortona
    City in Italy

    Cortona Italy
  3. Florence
    City in Italy

    Florence Italy
  4. Pisa
    Metro Area in PI Italy

    PI Italy
  5. Chianti
    Hotel in FI Italy

    FI Italy
    040 219971124
  6. Castiglion Fiorentino
    City in Italy

    Castiglion Fiorentino Italy
  7. Lucca
    Metro Area in LU Italy

    LU Italy
  8. Fiesole
    City in Italy

    Fiesole Italy