Tuscany town bound?

What is it about our North American genetic makeup?

We have an alarmingly high predisposition to the “Tuscan Holiday” syndrome.

At some point in our life, usually around a marriage, a divorce, or our 20th wedding anniversary, the symptoms become increasingly acute and we seek treatment.

Our cure?

Rolling hillsides. Chianti by the litre. And a rental car with extortionate day fees and a GPS dialed to an unpronounceable hill town.

The people affected by this syndrome are in the millions. The book, Under the Tuscan Sun sold over 2 million copies. The movie was a box office success and grossed over 60 million.

It’s true that there’s equally stunning scenery in other parts of Italy, but something about Under the Trento Alto Adige Sun or Under the Friuli Venezia Giulia Sun just doesn’t have the same ring to it.

So whether “Tuscan Holiday” is genetically predisposed or not, Tuscany is easily the most celebrated region in Italy to visit.

Which is the most popular town in Tuscany?

The most famous city is Florence of course. But the hot list also contains Pisa, Sienna, Lucca, San Gimignano and Cortona.

What’s an alternative to those places?

Do you want something a little lower key?

Would you like to find your own slice of paradiso in terracotta?

Then you’re gonna need a car.

And your gonna need some great ideas.

Sorry–you can’t have my car but you can steal my ideas.

I must tell you that I didn’t pick these towns. I never could have. When I lived in Italy I always deferred such choices to the locals. I just jumped in the car and went for the ride.

So for this list I asked my Italian friend to give me her best picks. I wanted “under the radar” and “picturesque”.

She gave me this list. If you visit her in Italy, this is where she would take you.

Now go forth. And dream with reckless abandon.

6 Towns in Tuscany Your Travel Agent Has Never Heard Of:

1. Pitigliano


Pitigliano is a medieval town with Etruscan heritage. It’s found in the southern Tuscan region of Maremma in the province of Grosseto.

The Maremma region is definitely my favorite region in Tuscany; it’s less popular than the hill towns of Chianti but it’s where Italians spend their summer holidays.

The earth under Pitigliano is riddled with tunnels, caves and tombs that you can explore – hook up with the local tourist office to arrange a tour. There’s also a Christian cave chapel said to be the oldest in Italy, from about 400 AD.

For the best views of the surrounding valley head to Piazza Becherini.

There’s no train service to Pitigliano–therefore a car rental is your only option other than a bus from Sienna or Florence.

2. Capalbio


Capalbio is also located in the province of Grosseto, close to the Lazio border.

The views from Capalbio give you an awesome picture of the entire Maremma region all the way to the sea.

The old and lovely things that attract people to the town are the Renaissance Collacchioni Palace which houses the piano of Giacomo Puccini–Capalbio’s most famous vacationer.

The main square has a 13 century church decorated with Romanesque architecture and Renaissance frescoes.

If looking at art commissioned by rich eccentrics is more your thing–head to the Tarot Garden featuring the 22 characters of the Tarot cards.

Wash it all away on the coast of Capalbio which is 12 kilometres of sandy beaches and clear water.

3. Manciano


The town of Manciano is built on a hilltop with massive views of the surrounding valleys and the sea. You can even see clearly to Giglio Island, where the Costa Concordia cruise ship sank.

Apart from the views, you wanna visit Manciano to enjoy the thermal hot springs.

Many people don’t know that Italy has some amazing natural springs and the Saturnia hot springs just outside of Manciano are famous within Italy.

You can pay for access to the thermal waters via the spas in Saturnia. The free access is just two kilometres outside of Saturnia at Mulino waterfalls, also known as Cascate del Gorello.

Manciano is just eleven miles SW of Pitigliano (above) so it would make sense to see them both on the same trip while you’re bombing around in your car.

4. Montescudaio


Montescudaio is a miniature Tuscan town with a whopping 1800 residents.

The village is a medieval borghi, a fortified town surrounded by protective walls. The town is located on a hill close to Pisa.

This is a beautifully preserved town where you might want to plunk yourself at a restaurant with a terrace with stunning views of the ocean, the Islands of Elba, Capraia, Giglio and Montecristo.  You’re just 12 km from the coast.

At the restaurant you’ll want to take a sip of the local product: Montescudaio D.O.C. wine. The red is made from the Sangiovese grapes and the white from the Trebbiano Toscano, and the D.O.C certification mean that the grapes are guaranteed to be from that tiny geographical area. No outsider grapes, man.

If you happen to be in Montescudaio in summer and you need some beach time, choose Marina di Cecina, Vada or Bibbona.

5. Montefioralle


If you dream of staying in a farmhouse in the famous hills of Chianti Classico then Montefioralle might be your golden ticket for under the radar Chianti living. It’s on the road between Florence and Sienna where vineyards, scattered peasant houses and beautiful villages are dotted between hill-top woods.

Montefioralle has just 2 restaurants and is virtually car free, so if you have kids then this would be a great place to relax.  It’s a 20 minute walk on foot to the popular village of Greve in Chianti, where you can visit a grocery store and see other humans apart from the 79 other residents who live in the Montefioralle.

6. Monteriggioni


Monteriggioni conforms perfectly to the mental image of a walled castle village.

The walls and towers are virtually intact and the streets are mostly traffic free.

Many Italian towns have festivals in the summer, but these people really know how to throw a party.  If you‘re visiting Italy in the summer – check out their medieval festival on the first weekend of July every year. I would recommend it as an alternative to Il Palio (the horse races) in Sienna – especially if are travelling with your kids or parents.

The locals dress in medieval costumes playing farmers, merchants, soldiers, cross-bowman friars, magicians, astrologists, ballad singers and jesters. Kids get in free. Their handlers, (us adults) gotta pay 10 euro.


This list is meant to give you a town in Tuscany worth visiting.

These towns are well preserved, picturesque and quaint. They are more terracotta than gold. More pappa al pomodoro than fusion cuisine.

And I guarantee the towns will be boring at night, which is sometimes, just what we need.


I’d love to hear from you.

Do you have any other suggestions?

Have you ever visited a small town in Tuscany?

Images: Pitigliano, Capalbio, Manciano, Montescudaio, Montefioralle, Monteriggioni



48 Responses

  1. Hi Bianca
    Funny I was just thinking of you and wondering when you were sending out the next Italian “fix”!

    I stayed for a month in Pistoia- it’s a market town and exactly 1/2 hour on train each way between Piza and Florence. Also buses – and good connection for day trips. The history is interesting- lots of art etc and cheaper to stay than Florence. Nice old villas on outskirts- restaurants etc
    One of these days – I hope to get back to Italy!!

    1. Hi Antoinette

      Thanks for bringing up Pistoia. They have a music festival every summer that draws big crowds.

      Glad to deliver your “fix”.

      As you can see, I have fun with it.

      xx Bianca

  2. This is a great post! I live in Chianti and I learned loads! Some great ideas I’ll pass on to our guests. Thanks Bianca!

    1. Hi Simon,

      Wow, I know you’re called the Tuscany Advisor on Twitter so that means a lot!

      xx Bianca

    1. Hey Sharon,

      Yes, the travel bug makes us itchy. That little bugger. It’s also contagious. xx Bianca

  3. Hi Bianca
    My friends and I are looking (just looking at this time) at your fabulous trips to Italy. Keep sending them. Never know when…..
    We just got back from seeing Julie & Dean and the rest of the kids in van. Hope you and your family are well.
    Good luck with the travel business. With all that enthusiasm I’m sure you will do well. Would love to join you sometime.

    1. Hi Ellie,

      Thanks so much for dropping by my digital home. Wish I could put the kettle on and make you tea. Thanks for your encouraging words. xx Bianca

  4. It is a good post for Tuscany Lover like me!!
    I got the best moment in Tuscany during my trip, I really love Tuscany and wanna visit all the places there.

    I also recommend Pienza, a small village but have a classic and stunning view of Tuscany!!

  5. Just came across your website which is perfect for an Italiophile like me! My uncle lives near Arezzo which is full of wonderful Renaissance frescoes and has an amazing antiques market on the first (or is it last) weekend of the month.

  6. So happy I discovered your site. We leave April 18 for three months in Italy, one month in Roccalbagna and one month in Le Marche area. It’s my first time and along with the major tourist cities, I most want to visit the small towns and less traveled regions.

    Great site and great sense of humor. Ciao!

  7. Hi Bianca,

    Thank you for this helpful post!! My husband and I are going to be in Tuscany in early September to celebrate our 1 year wedding anniversary. We plan to stay 4 nights in Florence, then 4 nights in Montepulciano (unless you recommend otherwise) and 3 nights in Rome. We are having a difficult time trying to decide whether we should stay in the town of Montelpulciano so we can go to dinner and have wine and walk home or if we should stay outside of the town in one of the bed and breakfasts in the outskirts? Any suggestions and recommendations would be greatly appreciated! Thanks so so much!!

    Claire Jessen

    1. I have been to Italy 4 times. 2 nights in Montepulciano is plenty because in my opinion you will be sorry if you don’t spend more time in Rome, if these are your only destinations. Staying in a hill town to me is an amazing experience.I would highly recommend that, over staying in the outskirts.

    2. I would do rome FIRST. 3 Days is probably just right for a first time Visit. But the frenetic pace is really a horrible way to end the vacation. September is a GREAT time to visit italy. I would honestly do organized walking tours in Rome to make the most of your time on Day one. if there’s something you like, go back and take a deeper look on day 2. after the pace of rome, head to florence, 4 days is enough. Then I would END the vacation in Tuscany. If you do it the way you planned, you’re essentially saving the best for the middle. In tuscany, I would book an agriturismo outside of san gimignano and drive around from there. Casolare Bucciano is my favorite. From there you can easily visit volterra, siena, colle val d’elsa, and some other choice towns.
      You can also visit Montepulciano and Montalcino in a day (half and half). When in Chianti, you MUST stop by Volpaia, a TINY little town that is drop dead gorgeous. the 2 restaurants in town are owned by the same family and they are fantastic.

      Good luck! Cheers.

  8. Hi
    Hi Bianca, this is really great timing as we head off today for Itay and will be travelling through and staying in Tuscany. We are spending 6 weeks in Italy this time and looking forward to the food, wine, exploring more small towns and having a culture fix…..such a wonderful country and people. I look forward to your next post.


  9. I’m looking for a quaint, charming hotel in a small village in the Tuscan region. Want to walk to dinner and. breakfast.

    1. Hi Sue,

      One place really sticks out in my mind for you.

      It is just outside of the beautiful Tuscan hill town of San Gimignanao. It’s a working organic farm, and they provide quaint rooms and wonderful food smack dab in the the centre of classic Tuscan countryside scenery.

      I sent my close friends there and it was their favourite place in all of Italy. They couldn’t stop talking about it.

      The pace is called Fattoria Poggio Alloro.

      Enjoy your trip and report back upon return!

      Baci, Bianca

      1. Ciao Bianca,
        We have stayed at Poggio Alloro. Beautiful, friendly…make sure to be there for dinner which is served family style so you can meet all guests and maybe a family member.
        Food is authentic and the meal is typical Italian in that it takes about 3 hrs to complete, but you are having so much fun with everyone you don’t notice, esther

    1. Ciao Tiana,

      Yes, my friend Rosa has a knack for showing me great little places I didn’t know about. Whenever she takes me to Genoa (where she lives), even if I’ve been many times, it always feels new because she knows so many hidden places.

      Thanks for your comment,


  10. Planning a week in Tuscany with two other couples in September or October. We’d like to spend the week in a villa that we can use as a home base for seeing the countryside. We’ll be renting a car (or two). We’re thinking that something within walking distance of a town or village would suit us fine. We’re a family of wine lovers and good food. We’ll be cooking some of the meals so access to a market is important. Any suggestions for such a location that would keep our interest for the week?

  11. Hi. I am spending 4 days/nights in Tuscany at teh end of April and was wondering where best to stay for those 4 nights? I fly out of Florence so will spend 2 days minimum there, but was wondering how best to split up the 4 days. I was considering 2 days Siena & 2 days Florence, or perhaps 1 day Siena & 3 days Florence. Or……. Any advice greatly appreciated. Many thanks

  12. Can I just tell you how much I love your website, posts, recommendations?!!! I’m planning a trip to Italy in June (Florence/Tuscany, Cinque Terre, Almafi Coast, and perhaps a day trip to Capri?!) Unfortunately, I’m leaving the week before your tour 🙁 I’m looking into everything you posted but if you have any recommendations for a solo traveler, would love LOVE to hear them! 🙂 (I’ve been to Rome, Venice, Milan, Florence before). I’m only there for 10 days so I realize this is ambitious! 🙂

  13. Ciao Bianca, I am so happy to have found your website as we are returning to Italy in Fall. This time just my husband and I to celebrate our 43rd anniversary. We want to visit the hilltowns, we love Siena and san Gimigniano and will return there, but want to spend 3-4 days wandering in and about others. Volterra has been suggested and I would like to visit Assisi. Any others you can think of?

  14. Hi Bianca,

    We’re in Italy in November and would really love to visit Cinque Terre. If we go in early november compared to late November, will it make a difference with regards to how much rain there will be?

    Will this be the same in Amalfi Coast as well?


  15. Hi,

    I love Florence and Siena is completely special. San Gimignano is magical particularly in the evenings when the tourists leave. I also think that the Bolgheri and Castagneto Carducci are well worth visiting, and the roman tree lined road between the two is stunning and if you do get to Bolgheri, visit il Taverna del Pittore its stunning and the food’s great and in the evenings the tables spill out into the roadside – totally magical….enjoy

    1. Thanks Charlotte!

      These are fantastic recommendations and I so appreciate you dropping by and letting us know. You rock!

      Happy travels,

  16. Thanks so much for this wonderful information. My husband and I will be travelling to Tuscany for approximately 1 week in mid-August next year. Our children will be 2 and 4 years of age at the time. We are wanting to know where we should base ourselves and whether it’s possible to stay less than 7 days in villa/farmstay accommodation. I have found quite a few blogs that state you must stay Saturday through to Saturday. Appreciate your thoughts

  17. Want to go from Lucca to Manciano to do hot springs.
    We do not want to drive. Is there a train or bus?

  18. Hi Bianca

    Thanks for the awesome recommendations. We will be staying in Florence for 8 nights in May. What town / location would you suggest for a day trip out? We do not drive so we need to use public transport 🙁


  19. Hi Bianca

    Thanks for the awesome recommendations. We will be staying in Florence for 8 nights in May. What town / location would you suggest for a day trip out? We do not drive so we need to use public transport 🙁


  20. Visitig Volterra in Tuscany is a dream that come true like all Tuscany: Firenze, Pisa Lucca Arezzo Siena San Gimignano, come in Tuscany!!

  21. Hi Bianca,

    I enjoyed reading your blog and the way you invite your readers to make the most of Italy. I would like your advise in my trip to the Tuscany this early July. I will head it from Rome to spend 5 days including one day and a night in Florence. i will be traveling with my wife and a 10 years old daughter. Where do you suggest us to stay as a base place to move around and what towns to visit. i am planning to rent a car. Thanks a lot and regards, jorge

  22. Hi Bianca! Love your website. I’m traveling to Tuscany at the end of this month. Good you make some recommendations for a place to stay. Hotel/villa? Any wine tasting and cooking classes? I’ll be there for 5 nights Thank you so much!

  23. Hi Bianca
    We are vacationing in Italy next year to celebrate our Wedding Anniversary. Any tips and advices where to go and what to see. We enjoy being amongst the locals. Obviously, we want to enjoy the famous landmarks but for the most part we like to getting lost in cities we visit and enjoy local foods. We are travelling with three teenagers who has travelled to the England and France.
    Amalfi Coast – Ravello (5 nights)
    Rome (3 nights)
    Agriturismo in San Gimignano (4 nights)
    Cinque Terre – Vernazza (3 nights)
    Venice (3 nights)

    Thank you!

  24. Hi Bianca,

    My husband and I wanted to vacation in Tuscany but also wanted to be near a beach.. We both love the Tuscan homes so can bring family its us.. Plus I am trying to plan to go southern France and hoping you can tell what part of Tuscany that near southern of France if it is…

  25. Bianca,
    Haven’t been to Europe in 32 years, husband and I are celebrating our 23rd wedding anniversary. Found a great airbnb in Orvieto. Was thinking about using it as our home base for 4 days as we explore the area- but perhaps our home base should be Sorano or Pitigliano: Do you have any advice? thank you so much for your resources!

  26. Hey Bianca!
    My partner and I are travelling to Toscane next week and I thought on following your guide from A to Z. We’d like to visit places where there’s not that much tourism so I think this is great! Is there any recommendation on this places where to have a great Tuscany delight? Thank you so much for this useful list and yet on 2015 your list will still serve to those on need.
    Thanks again, kisses and salutations from Belgium.


  28. Bianca,
    We will be driving from Rimini to La Spezia in early September. We have visited Bologna and Florence in the past. Can you recommend a scenic drive?


  29. Hello
    My name is Viraj and im from Mumbai, India.

    My wife and I will be travelling to Italy for 10 nights in June.
    We will be staying in Florence for 2 nights and in Tuscany for 2 nights.
    Please help advise us with where, what part of Tuscany should we live in. What would be best for 2 nights.


  30. Great site and helpful info. We are planning an Italy trip for June 2017 with our family of 5 (my wife and i, kids, 12, 10, 7). Tenative plan:
    First stop (after a few days in Rome) is Positano for 2 weeks, then a week in Tuscany and a week in Venice.

    Question is (besides is this a good game plan) what is a great Tuscany base? We have never been to Tuscany and seeking a great town where we can rent an updated farmhouse with a pool and view and ideally walking distance or close drive to a great town as well as close driving distance to other destinations that may be child friendly and memorable? Have pienza and cortona short list but overwhelmed with options.

    Thanks in advance.

  31. HI Bianca,
    My best friend is planning to get married in Tuscany in October and I have offered to help her pick a venue. Needless to say, once I started looking I became overwhelmed. What she wants is to be married in the town hall of a small town/village then have dinner in a local restaurant (nothing too fancy, just great food in a beautiful location and as she puts it with little Italian grandmothers making pasta in the kitchen). The food might be more important than the location to be honest. There will be max 20 people travelling from all across Canada from Vancouver to Newfoundland to attend the wedding. Could you help a sister out with a few suggestions for a magical day.


  32. Hello, i feel that i noticed you visited my
    site thus i got here to ?return the want?.I am attempting to to find issues to improve my web site!I guess its good enough to use
    a few of your ideas!!

Leave a Reply

Your email address will not be published. Required fields are marked *