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Tuscany, Florence, Siena

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. Anyone have any other suggestions?

22 Answers

top answer by
Matthew from Boston

Siena is a good 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 Horse Race, a horse race around the main square where each of the cities neighborhoods are represented by a rider. 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.

I'd also recommend  Montepulciano, if you eat pork, then grab yourself a porchetta panino (pork sandwhich) it is some of the best in Italy.  Fiesole is a really easy visit from Florence, just outside the city and it is filled with Roman ruins.

I would visit  Montalcino, home of the Brunello di Montalcino. Brunello is one of the best wines in Italy and renowned worldwide. One of my favorite day trips I took when living in Florence was here just because of the lunch with wine. Definitely try some of these wines. If you still want more small towns then check out  Arezzo and  Pienza.

While in Florence I would recommend eating at  Acqua Al 2. They have opened two in the States (one in DC, one in SD), but this is the original and much better than their expansions. Try either the balsamic steak or blueberry steak (I know it sounds strange, but it has a blueberry garnish that is amazing). Another restaurant that I highly recommend in Florence is  Golden View Open Bar. I know the name looks strange, but it is situated on right on the Arno just next to  Ponte Vecchio. It has an amazing view and I recommend either the truffle chicken, truffle ravioli, or pasta with a boar meat sauce. Just a heads up, as with most restaurants in Italy, portions tend to be smaller. 

No trip to Italy is complete without good pizza, and while the country invented it, there are a lot of places that are not very good, meant for tourists. The best pizza I had in Florence was  Pizzeria Spera (Via Cernaia 9r, 50129 Florence, Italy). If you have time, go in and sit down, grab a liter of the house wine (last time I was there it was only 5 Euros) and enjoy. 

Mentioned in this answer:

  1. Palio Horse Race (attraction)
  2. Montepulciano (city)
  3. Fiesole (city)
  4. Montalcino (city)
  5. Arezzo (city)
  6. Pienza (city)
  7. Acqua Al 2 (restaurant)
  8. Golden View Open Bar (restaurant)
  9. Ponte Vecchio (attraction)
  10. Pizzeria Spera (restaurant)
  11. Siena (city)
15 thankscomments (4)

answered by
Victoria from Riga

Andreas, there are plenty of things to add. If you are going to take a longer trip to the sea, I'm also voting for Cinque Terre, but definitely visit immensely beautiful cities Lucca and  Portofino.

Right around Florence there are so many gorgeous little towns and one of the best wineries in the world.

When you will go to Siena, on the way back I highly recommend paying a visit to the butcher restaurant of Dario Cecchini. His is a local celebrity, his steaks are incredible. His is making people from all over the world happy at his restaurant Officina della Bistecca (Via XX Luglio, 11
50022 Panzano in Chianti – Fi – Italia) in  Panzano in Chianti.

Book in advance. Website.

His wife Kim is dealing with all bookings. I recommend going there while it is still day light, the roads are so picturesque.

Half an hour away from Florence there is a beautiful town called Tavarnelle Val di Pesa with a castle and amazing restaurant L'Antica Scuderia (via di Passignano 17 - 50028 Tavarnelle Val di Pesa (FI)) with an incredible wine collection. It is a restaurant of the Antinori actually.  website

Hope this helps!

Mentioned in this answer:

  1. Cinque Terre (region)
  2. Lucca (city)
  3. Portofino (city)
  4. Panzano in Chianti (attraction)
  5. Tavarnelle Val di Pesa (city)
  6. Officina della Bistecca (restaurant)
  7. L'Antica Scuderia (restaurant)
10 thankscomments (2)

answered by
Caterina from Florence

I agree with your friend: YOU HAVE TO SEE SIENA and walk uphill until you reach its fantastic Cathedral... only after that you can continue to famous Piazza del Campo and seat down right on the Square pavement (very romantic in my opinion, especially at night).

I also recommend Montepulciano (where some Twilight scenes were filmed),

Pienza (the Ideal City of the Renaissance + UNESCO World Heritage site),

Pitigliano (entirely built on a tuff hill)

and Bagno Vignoni (very well known for its 16th-century rectangular tank containing the original source of water that comes from the underground aquifer of volcanic origins)

and of course Fiesole (take your girlfriend here La Reggia degli Etruschi... ;-) the best restaurant with view).

If you are interested, you can check out this website and discover some itineraries I personally wrote years ago. I hope it may help, Tuscany is literally filled with wonders... almost impossible to mention them all!

Have a great time in my Region!


Mentioned in this answer:

  1. Piazza del Campo (attraction)
  2. Montepulciano (city)
  3. Pienza (city)
  4. Pitigliano (city)
  5. Bagno Vignoni (attraction)
  6. Fiesole (attraction)
  7. La Reggia degli Etruschi (restaurant)
6 thankscomments (4)

answered by
Carina from San Francisco

As a former study-abroad student residing in Florence, Italy, I can confidently say that all of the answers so far have been spot-on! However,  I feel inclined to mention the exquisite little town of Fiesole! 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. 

I almost forgot- getting to Fiesole is almost the most fun part! You simply take the Number 7 bus out of Florence, and let your wild ride ensue: the Italian bus drivers are notorious for their ability to operate their massive vehicles in a manner similar to a roller coaster. As you ascend upwards from Florence, not only does the view get better, but the extremely windy roads also make the ride more of an adventure. Hanging on to anything (literally, anything) is a definite must to survive the ride. Haha!

I hope that this answer will provide you with a nice inhalation of fresh air on your trip!

Mentioned in this answer:

  1. Florence (city)
  2. Fiesole (city)
5 thankscomments (1)

answered by
Yuka from Osaka

I recommend two cities around Florence. Lucca is very lovely city surrounded by walls and perfect to explore by foot. 

Another is Orvieto. This city is not in Tuscany but you can visit there in an hour and a half from Florence. Orivieto has the beautiful and huge cathedral.

Have a nice trip!

Mentioned in this answer:

  1. Lucca (city)
  2. Orvieto (city)
4 thankscomments (2)

answered by
Tiffany from Corvallis

All of the above.  Seriously. If you have time, do everything. Tuscany is so rich with beauty and culture.

Florence is stunning, so it's great you're staying there. You could easily spend a week there and probably still not have fully 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. (My Florence blog post)

We really enjoyed San Gimignano. You need a day there to explore - seriously beautiful and do stop and have gelato by the entrance gate. It's just on the left as you enter - a family run business wih the best gelato I had in Italy. No contest. (Photos and the ice cream shop)

Siena is another that you will want a full day in. Look into local festivals in these towns before you go so that you can either catch one or avoid one depending on your interest. Siena has some really amazing festivals.

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.  Close by is Pisa. It's easy to see both towns in a day if you're short on time, but if you want to stroll the wall in Lucca and relax and enjoy your time Italian style, then a day for each would be great. Pisa is smaller with less to see outside the obvious attractions. There is more than the Leaning Tower of Pisa though - 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 sun set. 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 a great foccacia shop here that's easy to find.

We drove to Cinque Terre, but driving was difficult and parking was nearly impossible - and that was in the winter. Take the train. Or a boat. Just don't drive. But do go. It absolutely warrants a trip.

Mentioned in this answer:

  1. Florence (city)
  2. Piazzale Michelangelo (attraction)
  3. Borgo Antico (restaurant)
  4. Pisa (city)
  5. Leaning Tower of Pisa (attraction)
  6. Marina Di Pisa (attraction)
  7. Cinque Terre (region)
  8. San Gimignano (city)
  9. Lucca (city)
  10. Siena (city)
4 thankscomments (1)

answered by
Augusto from Puerto Rico

You guys should also go to San Gimignano with its mideval towers, Volterra an its roman theater, Montalcino  and taste the Brunello, Pienza small but beautiful, Montepulciano also a romantic  wine town and Cortona is the tipical mideval Tuscan town that makes you feel you time traveled.

Mentioned in this answer:

  1. San Gimignano (city)
  2. Volterra (city)
  3. Montepulciano (city)
  4. Cortona (city)
  5. Pienza (city)
  6. Montalcino (city)
4 thankscomments (1)

answered by
alessandro from Asciano


of course you have not to miss Siena (you can have a nice lunch as a local at Osteria da Trombicche in Via delle Terme). Other fantastic daily trip could be at Greve In Chianti and Panzano in Chianti. You can try to organize a wine cellar visit (Fontodi Winery in Greve in Chianti could be a good spot, they do free visits and tastings, they are organic producers) and you can have lunch at Solociccia, Dario Cecchini's restaurant. Othere 2 places that you should visit are Volterra and Certaldo.


alessandro draghi

agriturismo il molinello

Mentioned in this answer:

  1. Osteria da Trombicche (restaurant)
  2. Panzano in Chianti (attraction)
  3. Volterra (city)
  4. Certaldo (city)
  5. Fontodi Winery (attraction)
  6. Solociccia (restaurant)
  7. Siena (city)
  8. Greve In Chianti (city)
3 thanks

answered by
Alessia from Dicomano

You should visit the Chianti countryside and its wonderful Medieval villages (as San Gimignano, Monteriggioni) and the beautiful city of Siena

Mentioned in this answer:

  1. Chianti (attraction)
  2. San Gimignano (city)
  3. Monteriggioni (city)
  4. Siena (city)
3 thankscomments (1)

answered by
Andrea from Tampa

You should most certainly take a day trip to the Brunello region! Chianti is wonderful, but the Brunello is such a different wine. We took a trip with Tuscan Escapes, and it was the best!

Mentioned in this answer:

  1. Brunello (region)
  2. Chianti (attraction)
3 thankscomments (1)

answered by
Beckah from Minneapolis

Siena is a beautiful city that you should absolutely spend some time in. If you are active, hop on a bike with Florence by Bike and take a tour of the Chianti countryside to a private farmhouse for a delicious lunch prepared by the owner. My mother and I did this when she was visiting while I was studying abroad in Siena and we loved it!

Mentioned in this answer:

  1. Chianti (attraction)
  2. Siena (city)
2 thankscomments (1)

answered by

There is a lot to visit around florence:

- San Gimignano

- Certaldo

- Artimino (near Carmignano)

- Montespertoli

These are all small villages where you can find good restaurants and wine.

Mentioned in this answer:

  1. San Gimignano (city)
  2. Certaldo (city)
  3. Carmignano (city)
  4. Montespertoli (city)
  5. Artimino (attraction)
2 thankscomments (1)

answered by
Paul from Amsterdam

You could go on a day trip through the  Chianti region, and visit some cute little villages there.  Greve In Chianti and  Castellina in Chianti are both wonderful, and there are a couple more. A bit further away, but also worth it is  Cortona, a small village on the slope of a hill. From there, you could also visit the  Lago Trasimeno, and visit the isle.

Mentioned in this answer:

  1. Chianti (attraction)
  2. Castellina in Chianti (city)
  3. Cortona (city)
  4. Lago Trasimeno (attraction)
  5. Greve In Chianti (city)
2 thankscomments (1)

answered by
Cristina from Enna

Isola d'Elba. San Gimignano, Arezzo, have a tour all around tuscany. If you'll stay longer you can also cross the regional border. Public transports are very well organized but if you have the possibility to rent a car u can stop wherever you like.

Enjoy your holidays!

Mentioned in this answer:

  1. San Gimignano (city)
  2. Arezzo (city)
  3. Isola d'Elba (attraction)
2 thankscomments (1)

answered first by
frieso from Brussels

Arezzo, MontepulcianoSan Gimignano and if you have a few days, the coastal region of Cinque Terre is amazing.

Mentioned in this answer:

  1. Arezzo (city)
  2. Montepulciano (city)
  3. San Gimignano (city)
  4. Cinque Terre (region)
2 thankscomments (3)

answered by
maria from Chiavari

Lucca is a medioval town, is beautiful.
Pisa with the pending tower.


Mentioned in this answer:

  1. Lucca (city)
  2. Pisa (city)
  3. Arezzo (city)
1 thankscomments (1)

answered by
Andrew from Fort Lauderdale

Going to be a little critical and tell you that had I missed out on visiting Pisa - it would have been better spent elsewhere. 

Mentioned in this answer:

  1. Pisa (city)
1 thankscomments (1)

answered by

Mentioned in this answer:

  1. San Gimignano (city)
1 thankscomments (1)

answered by

Mentioned in this answer:

  1. Montepulciano (city)
  2. Pienza (city)
  3. Montalcino (city)
  4. Lucca (city)
1 thanks

answered by
Christine from Philadelphia

Monteriggioni is a great place. It's a day or half-day trip; there's enough to do to last a couple hours, and it's far enough away from Florence that the traveling there and activities will take up at least half a day.

Mentioned in this answer:

  1. Florence (city)
  2. Monteriggioni (city)
1 thankscomments (1)

answered by
Marco from Bergamo

Mentioned in this answer:

  1. Monteriggioni (city)

answered by
Tina from Livorno, Italy

I propose an itinerary a bit off the beaten track, in the very heart of Tuscany, starting from...Micciano, a small little village with 34 habitants, surrounded by a natural park where in May you can find rare wilde flowers! There You can eat at Osteria Del Borgo, calling Anna before ( you need to reserve, it is really a small hosteria) . Where the weather is good, You can see the sea from there! So you can decide to go to the coast, or decide to vist Volterra. Volterra, the very Etruscan land! You will sudden understand why Romans put about 100 years to take it !

First of all then I strongly recommend Museo Etrusco Guarnacci, the Etruscan museum. Just in front of it there is a very popular wine bar, La Vena di Vino where you can drink a nice glass of local red wine, or if You go in Volterra in the evening, you can't miss Caffe dei Fornelli where in the week end you can listen at good live jazz music! If You rather prefer ice cream, Chic & Shock is the one for You!

In Volterra there where noble and powerful families, one of these was the Viti family, that had its country manor at Mazzolla, a very incredible little village preserving the image of the past. You will find it in the way to Siena. There please eat at Trattoria Albana, You will adore it, and maybe drink a glass of our wine, we will be happy!


Mentioned in this answer:

  1. Volterra (city)
  2. Micciano (city)
  3. Osteria Del Borgo (restaurant)
  4. Museo Etrusco Guarnacci (attraction)
  5. La Vena di Vino (attraction)
  6. Caffe dei Fornelli (attraction)
  7. Chic & Shock (attraction)
  8. Mazzolla (city)
  9. Trattoria Albana (restaurant)
  10. Siena (city)

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