Irresistible. Mesmerizing. Addictive. Italy weaves a magical spell on travelers. The food, the wine, the friendly people, the culture, the history, but none so entrancing as the Italian hill towns of Tuscany. One visit is never enough. No matter how long the stay once home, travelers long for glorious days of exploring vineyards and ancient hilltop towns.
Frequently asked for travel advice, the small towns of Italy often make the top of our suggestion list. Safe, slow-paced and jaw dropping beautiful, it is hard to go wrong with a stay in almost any of the Italian hill towns.
But where to go in Tuscany? With so many astounding hill towns in Italy, the prospect of planning can be overwhelming.
Below we list five of what we believe to be the best Italian hill towns. We hear the arguments beginning as dozens of other towns should make the list.
Below each of the locations chosen you will find our recommendations for the best places to stay in Tuscany. Our choice is one we have stayed in ourselves and is typically mid range price. Hill towns of Italy tried and tested.
A budget and luxury hotel has also been added for you to compare.
We will tell you what we loved about the Tuscany destination and also what we think you should be aware of before booking. We have not been sponsored by any of the hotels.
Where to stay in the Italian hill towns of Tuscany
Cortona
Little did Frances Mayes know what her romantic telling of her paradise ‘Under The Tuscan Sun’ would bring. Cortona, perching on hills that seem to bow down before its own beauty, made an incredible setting for the best selling book and subsequent film. The home Mayes occupied in one of the most beautiful Italian hill towns became so popular she felt the need to escape and left Cortona.
Retaining much of its 3000 year old history behind Etruscan stonewalls, Cortona delights with stunning views, medieval architecture, quaint shops and restaurants offering traditional and local cuisine. The charming city offers some of the best views in Tuscany.
Cortona under the Tuscan sun
Where to stay in Cortona
We stayed at Hotel San Michele
What we liked about Hotel San Michele
Besides being the most central of all accommodations in this walled Tuscan city, Hotel San Michele is within the 15th century Baldelli Place. Beautifully restored, the Ministry of Cultural Heritage lists the hotel as a national monument.
Furnished with antiques, the hotel is modernized with amenities and facilities. Each of the 40 rooms is uniquely designed. We took the short walk to the main square where stands of delicious chocolates and local artisan wares are sold.
Ask the staff to point out the wall painting of Madonna with child dating to the 1400’s. It feels a bit like traveling back in time with all the conveniences of modern day.
What we want you to know about Hotel San Michele
The hotel is on a hill. Welcome to Italian hill towns. When leaving or arriving you will be immediately heading uphill or down. This was not an issue for us but we do want you to be aware of the incline if you have significant mobility challenges.
Sitting area in Hotel San Michele
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Sorano
This ancient medieval Italy hill town is often referred to as the City of Tufa. Given its perching placement on volcanic tufa stone it comes by its nickname honestly.
Sorano retains much of the activity of centuries ago. Hovering above the Lente River, the hilltop town is surrounded by vineyards, fields of wheat, olive groves and grazing sheep.
Thought to be inhabited as far back at 3rd century BC, the Etruscans found the porous volcanic rock easily carved. Caves cut out centuries ago for tombs and hideaways are today used as garages and storage sheds. Talk about re-using and re-purposing!
View of Sorano from hotel window of Hotel Fortezza
Where to stay in Sorano
We stayed at Hotel Della Fortezza
What we liked about Hotel Della Fortezza
This one of a kind hotel is within the Fortezza Orsini di Sorano fortress. Walking across the drawbridge over a moat to one’s accommodation is not something we have ever encountered. The rooms each have a different design, some more spacious than others, but all with extraordinary views of Sorano.
Located in the center of this Italian hilltop town, exploring the ancient stone and stucco buildings of Sorano is easily done. Or if you have had enough of walking hill towns in Italy have a refreshment in the courtyard of your own castle.
What we want you to know about Hotel Della Fortezza
This is not a deluxe hotel. The hotel is decorated in good taste and fits well with the age of the building. As you will guess that since it is an ancient fortress, the hotel sits at the very top of what we consider one of the best Italian hill towns we visited. Exploring the town on foot requires significant stair climbing.
Who doesn’t want to stay in a castle in Tuscany?
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San Casciano
The quiet Tuscan village sitting atop a hill (how unusual in Italy we know) can be found mere minutes south of Florence. Away from rush of one of Italy’s busiest cities, taking haven in San Casciano is one of the best of Tuscany.
As part of the agricultural area of Chianti, the local restaurants serve extraordinary wines, extra virgin olive oil and organic food of the region. The village is small but has good restaurants and pubs. Little shops sell groceries and pastries. During our visit, which happened to be on a Saturday, a marketplace was set up on main street.
One of the more secluded Italian hill towns San Casciano
We stayed at Sette Querce
What we liked about Sette Querce
Sitting at the edge of this Italian hill town, each guest has an entire suite. Arriving after a day of cycling, how luxurious to have a small kitchen and living area with a sofa. So much space to spread out our gear.
Each of the suites has a small terrace and the building is surrounded by oak trees. Breakfast is served to each of the brightly colored rooms. Frankly I found it challenging to pack up and get back on my bike. Home away from home in this Tuscany destination.
What we want you to know about Sette Querce
With the hotel being surrounded by beautiful trees, the views at Sette Querce tend to be of the forest and the village. The dramatic vistas of Tuscan rolling hills are more easily seen from viewpoints within San Casciano.
Kitchen area in room at Hotel Sette Querce
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Montepulciano
Known around the world for the wine produced in the area, Montepulciano towers over the rolling hills sitting atop a 2000 foot limestone ridge. Not far from the larger city of Sienna, the walls of this Tuscan city date to the 14th century. Evidence has recently shown Montepulciano was in existence as early as the 4th-3rd centuries BC.
Stretching for 1.5 kms (0.9 mi), the main street of this hill town of Italy will ensure you have a thorough work out. With car-free streets, blissful meandering among shops and wine tasting venues Montepulciano receives high points from visitors.
The city is well known for its ancient churches and Renaissance history. Perhaps most stunning of all are the astounding panoramic views of the valleys that surround one of the best situated Italian hill towns.
Montepulciano
We stayed at Villa Cicolina
What we liked about Villa Cicolina
Once a noble family called Villa Cicolina their retreat. With frescoed ceilings and antique furniture one feels as though you may be apt to meet royalty on the way to the infinity pool.
Located outside the city, the flowers and fields surround the entire property. Garden areas and walkways lead to a small church should you be so inclined. The olive trees near the pool provide welcome shade from the Tuscan sun.
What we want you to know about Villa Cicolina
Sitting outside of Montepulicano will mean you need to drive into the city or cycle. If you are looking to walk easily to amenities during your stay then this may not be the right spot for you.
Villa Cicolina infinity pool looking over the Tuscan hills
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Bagno Vignoni
Located in the heart of Tuscany, Bagno Vignoni is best known for its thermal waters. The springs of this Italian hill town have been soothing travelers since Roman times. At the end of a day of cycling the Italian hills, peering at the famous waters held in a 16th century rectangular tank, the temptation to jump in, bike and all, crosses my mind.
Pilgrims of ancient times slogging to Rome stopped in Bagno Vignoni to soak in the waters springing from a volcanic aquifer. The hot springs definitely have staying power and still draw tourists to the town surrounded by the valley of the Orcia River.
We stayed at Hotel Osteria Dell’Orcia
What we liked about Hotel Osteria Dell’Orcia
The setting of Hotel Osteria Dell’Orcia may be on of the most beautiful in Tuscany. Nestled just below one of the quaintest Italian hill towns, rich with history, the rolling hills go on forever.
As the sun set silhouetting the cyprus trees, we meandered through the pristine gardens. I still recall turning to Hubby and suggesting we should come back for a month. Following one of the most delicious dinners we had in Tuscany I suggested we move in permanently.
What we want you to know about Hotel Osteria Dell’Orcia
The hotel is a five minute walk across a foot bridge to Bagno Vignoni. Call him a unique watch dog or town crier, the hotel also has a resident donkey.
Originally purchased with the thought of giving rides to children of guests, donkey was not keen on the idea of trotting wee ones around. Thinking better of it, the owner changed donkey’s role to marketing.
Hotel Osteria Dell’Orcia is well known for the hee-haw calling tourists to inquire why there is a donkey. Once on site the beauty of the setting is hard to resist.
Hotel Osteria Dell’Orca
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beautiful blue skies, with the promise of more to come… great pictures.. inviting.. thanks =^_^=
Tuscany is truly one beautiful scene after another. Happy to share our fond memories with you.
Mmmmm glorious! So many places still to explore in Italy and your post is helpful in highlighting your favorites and for good reason. After reading this enticing post you have made me dream of a return visit soon!
Peta
Peta I am delighted to hear the post brought to mind future visits to Italy. Time after time of pulling this information together for those asking us where to go in Tuscany, I felt it might be something others would be interested in too. Hard to resist the endless rolling hills and the history of the little towns sprinkled on the hills of Italy.
Great photos, so lush and green. ❤️
Thank you John. Knowing how much you love driving and taking photos on your journeys Tuscany would be a delight.
Indeed! ❤️
Waving a magic wand and we will see you in Tuscany! 🙂
Fantastic post, Sue — so thorough and inviting. Each town looks dreamy, with the hill-top vistas, and the numerous accommodations you offer, along with helpful details about accessibility–all sound wonderful. Your photos did a great job of capturing the hill effect, and your verbiage did too. Grazi.
You are very kind Jet and I appreciate the generous feedback. For years we have been dishing out advice on visiting Italy so it seemed reasonable, and hopefully more thorough, to keep all of our recommendations in one spot. It’s rare that any one place is perfect so we hope we have given a balanced description. Wishing you a good weekend and may we find ourselves in those rolling hills of Tuscany again one day.
Gosh, beautiful Tuscany so nicely presented, Sue and Dave. It looks very inviting indeed, gorgeous photography and wellwritten as always. I hope they get their rooms all booked! 🙂
Wishing you a wonderful weekend. In England is the last Bankholiday -Ruhe vor dem Sturm … 😉
Thank you for the lovely feedback. Tuscany has so many gorgeous spots to stay. We hope the piece will be helpful for those planning to go to Italy.
As this place is on my bucket list (the MUST do one) I appreciate this post so much. Just looking at the photos and descriptions gives me travel lust 🙂 Great job. I’ll bookmark this one for future planning, booking.
Wendy we will be happy to chat more about Tuscany and these lesser known spots. Wait I have an idea! ( Dave sighs as he hears me with another idea) We’ll come along and spend days exploring vineyards and hill top towns.
I was hoping you’d say that!
Wonderful! Let’s hatch a plan.
great post and very informative as always, Sue. perfect too for we are going to italy in december and planning on visiting a tuscan town or two. thank you!
Wonderful to hear of your upcoming trip Lola and that the post might be helpful in narrowing down the choices if hill towns to visit.
Very helpful info should I ever get there. Thanks!
You are most welcome Carrie. An easy trip in comparison to some. I think Tuscany would be an incredible spot to do some writing.
Sigh. You’ve brought back wonderful memories. We stayed in a glorious six-room villa at Montepulciano with four other couples a few summers ago. July, so it was hot hot (90s) but the villa was old with thick walls, cool enough that we never wished for AC. And the pool was delicious. Lots of walking for us (no biking) and used our rental car for day trips to Florence, Sienna, etc. A friend of mine biked Italy with her (super strong biking) husband recently. She rented an electric bike and said it was fantastic. Did you see many of those on your biking journeys?
Your time in Montepulciano sounds fabulous. We loved it there and definitely would go back for an extended stay. I can see why your friend would find an electric bike fabulous. Yes starting to see them more and more. On this cycling tour in Tuscany one of the riders had recently injured her knee so the bike allowed her to do the tour. Also it makes me happy knowing I will be able to cycle for decades, moving to an e-bike as needed.
Ah, nice to know you don’t snub the idea of an e-bike. Another friend (who has done 100-mile races, etc.) has hurt her foot (surgery, etc.) and rented an e-bike for a 3-day ride with friends. She loved it! 🙂
I think anything that gets folks out enjoying this amazing world of ours is fantastic. Electric wheelchairs to bikes it’s all excellent! Glad to hear the while worked so well for your friend.
Makes me want to revisit Tuscany! Great information. Thank you, Sue!
Like you Amy I could return in a heartbeat. You are most welcome.
Oh I’m drooling Sue. I want to go back to Tuscany and explore more NOW! I can’t believe we didn’t get to any of these places!!! But we did get to several others. So much world, so little time.
Alison
I am so with you. We have been to Italy numerous times and still so many places we haven’t been. Putting the post together definitely made me long for Tuscany again.
Will save this for when we go to Tuscany.
Hope you find it helpful Darlene!
Hi Sue, what a fabulously comprehensive and helpful guide for anyone thinking of visiting! I’ve never been to Tuscany but it’s certainly somewhere I want to go. Have you seen the movie ‘Letters to Juliet’? Much of that is filmed in Tuscany – I just love that film, I know it’s really just a sappy Hollywood romance movie, but it’s so beautiful in many ways, reading your post here has made me want to watch it again (I think I’ve only seen it twice, so that’s ok 🙂 )
I have not seen Letters to Juliet but will now be on the hunt for it Vanessa. Thanks kindly for the feedback and I do hope the guide will be helpful. If nothing else it will be an easy way for me to answer travel advice questions rather than digging through links on an individual basis.
It looks like you had a marvellous holiday in the Greek islands. Perhaps one day it will be Tuscany.
I’m still sighing! It could be just what the doctor ordered, Sue. Except that after I’d dabbled my toes in that infinity pool I’d have to be up and off, chasing my shadow again! No rest for the wicked. 🙂 🙂 Beautifully done. I’d be happy with any of them.
Imagine the walking to be done in Tuscany Jo. So many ancient buildings to be explored and wee places to be discovered. Like you I’d be happy to be based in any of the locations. Meet you there!
That’s a plan, Sue! And very tempting 🙂 🙂 It’s somewhat grey here.
Hoping sunny skies are coming your way Jo. We have had the most brilliant summer and feeling very fortunate.
‘ short walk to the main square where stands of delicious chocolates and local artisan wares are sold.’ I can only imagine how enticing the walk from your hotel in Cortona to the main square – always hard to resist chocolate especially if you love the sweet stuff 🙂 Sounds like you stayed at a variety of places, and you also got to experience the local marketplaces like the one in San Casciano and come across such quaint, stunning views. In a way it sounds like pace of life slowed down for you and company while you were there 🙂
Mabel perhaps that is what I love so much about Tuscany. The slower pace and the feeling of peacefulness. It comes from the friendly people, the stunning landscapes and oh yes the delicious food and wine. We enjoyed it so much.
This is my new goal in life. I want to write a book, have them make the movie, and ruin some quaint little town somewhere. Elizabeth Gilbert did it to Bali. Mayes, here. Badfish…hmmmm.
Badfish in this case Mayes felt the attention she received from people coming to the house she lived in was the issue. Luckily Cortona itself retained its charm. When we were there it just seemed like a beautiful slow paced spot to meander about in. Unlike coastal Italian towns that are feeling the crush of the cruise ship industry, Cortona isn’t next door to a port or a large center. I hear you though. Places like Cinque Terri and Venice are drowning in tourism.
Ah the Tuscany way of life sounds awfully much like how I would like to spend my weekdays, doing nothing…hahaha..too bad for work…I love the idea of staying in an old fortress though! Although I imagine my legs wouldn’t be too happy with me for a while…thanks for the summary of places for me to think of for future plans Sue…:)
I think Tuscany is one of those great places where you can get tons of exercise or just sit back and relax all day long in the beauty. Happy to share what we loved about Tuscany. I cant think of anyone I wouldn’t recommend it to.
Wow, what amazing scenery! Tuscany is one place I’d love to explore, partly because of the beautiful views and history, but mostly because I’ve heard the food is wonderful! Thank you for the hotel recommendations – if I ever make it over there, I’ll know where to start. 🙂
We would highly recommend Tuscany Dianne. I think you would like the slow pace, the serene beauty and oh my goodness the food is ridiculously good. I do hope you make it there one day.
Well that’s a lovely list to choose from Sue. From your photos I like the look of San Casciano . I’d like to go there.
I enjoyed Verona and Assisi when I was in Italy. I stayed in monasteries and convents that were very comfortable, quiet and close to attractions.
San Casciano is perfect. So quaint and quiet but so close to a larger center. My guess is that it is hard to go wrong in the area. The accommodations you chose sound so serene.
I never felt as if I was reading reviews on hotel in Italy, it was as if I was going through a story of Italy and as a tourist I was able to see through the lanes and by-lanes, antique furniture, medieval architecture, stunning views of the picturesque valleys, the vineyards to the oak forest to the hot water spring and the old castle to the new interiors inside those hotels, the painting to the panoramic view…I was enjoying every bit of the journey with you.
What really stuck to me is the “Hotel San Michelle”, as it is the book that is one of my most favorite one, the book “The Story of San Michelle” by Alex Munthe. I don’t know whether you have read it. This is such a wonderful book and the story is deeply seeped into my mind and it is there in my world, I keep analyzing it and I have kept it a secret to unearth when I visit Italy, and with so much to explore and enjoy it has to be a little longer trip. I have read and want to see the “Villa San Michele in Anacapri that was the dream home of the Swedish physician, Axel Munthe.
Munthe first came to Capri in 1885. He built his villa on the ruins of an ancient Chapel dedicated to San Michele…
Thanks Sue for reminding and making me nostalgic of a book I am so fond of.
😀
Nihar your comment makes me very happy as I definitely hoped to give readers a feel of the places not just cold, hard facts. How wonderful that the post triggered your fond memories of the book. I have not read it but can feel through your words the inspiring visions and descriptions it brought forth. Italy is a fabulous country that we have been fortunate to explore several times. The Capri area along the Amalfi Coast is stunning as well. Sending very best wishes and hoping one day you can find these places for yourself.
Thanks Sue and yes I will definitely make a visit to the place I have got so much involved while reading the book. Capri must be beautiful place and the location must be as captivating as described by you for other places surrounding Italy.
Your posts have always been so beautifully presented it doesn’t give a feeling of just reading it but truly experiencing it.
😀
Nihar you truly are a kind soul to shower such generous praise on us. Many sincere thanks. I have read your very interesting article on storytelling which is a subject near and dear to me. I am having issues commenting on my phone so how to visit on my desktop later today.
I am always so inspired by your travel and adventurous stories and stories is what I look around and such fabulous stories from your desk keeps me meaningfully engaged. Thanks as always Sue.
😀
So generous of you Nihar. My heartfelt thanks for your ongoing support.
Always my pleasure Sue and wonderful sharing thoughts with you.
😀
My children and their family always go to Tuscany, as a vacation. Tuscany is one of many beautiful vacations spots in Italy 🙂 Thank you for share Sue.
How wonderful to have family vacations in Tuscany! Happy to share some of our special places.
Everything looks beyond gorgeous Sue! Amazing snaps too. I am not a huge Europe fan only because I prefer to hang in the tropics but Tuscany is one of the few places I need to see there. The views, the architecture and overall feel of the place suggests that it’s a paradise.
I think you would like Tuscany Ryan. So much exploring, wide open space and did I mention the food and wine? It’s a very relaxed way to travel. Not to worry it can be very hot there so if that’s what you like try July and August. As a Canadian I tend to melt into a pool of sweat for fall is my best time. Besides i love watching the harvesting of the grapes. Always a pleasure to see you here Ryan. Much appreciated.
So very beautiful! Ever since I saw “Under the Tuscan Sun,” like everyone else I’ve wanted to go there! Thanks for this wonderful post, Sue! 😀
Linda it is as beautiful as the book makes it out to be. i hope one day you can see it for yourself. Thanks so much for your kind words.
I loved Under a Tuscan Sun! Loved the movie and everything about the whole get away and do something different thing. Having just come back from South Australia and the wine districts surrounding it, there are little mini areas with an Australian twist to Italian wine areas. You make it seem irresistible:)
Annie Tuscany really is addictive. We could definitely see ourselves spending a month or more there once Dave is retired. We would also love to explore more of the wine regions of Australia. Following our wonderful visit with you in Tasmania we did spend a day with another blogger who showed us around the wineries of Geelong. Such pretty country.
Sadly, even though my partner is Italian (and lived in Chianti for 6 years), I’ve never been to Tuscany …but now I want to visit more than ever ?. But I need to finish my circumnavigation first as this looks like a place that would be difficult to leave
Oh yes good point about not ever wanting to leave Tuscany. One day when you are old and finished sailing perhaps this could be a lovely place to spend some time.
What a great post Sue….our daughter and son-in-law just got back last month…2nd trip for them as they explore the region! My brother and his wife just got back and they loved the area….I feel a trip in our future!! Again, great post…beautiful pictures and very informative!
Kirt it sounds like they have paved the way for a future trip. I really can’t think of anything bad to say about Tuscany. A rental car is almost a must f you want to explore the smaller towns. Other than that it is a slower pace than Italian cities and the landscape speaks for itself. Thanks kindly for the generous feedback.
Ahhh – Italy! You are truly in my blood and in my heart <3
Each time I've returned, I considered myself blessed.
That is a wonderful way to word it Joanne. A blessing to be able to visit. Here’s hoping we return yet again to that amazing country.
Italy has been on my wishlist for the longest time. There are just so many things to see in the country! I haven’t been to Europe for ten years now, and you just gave me an idea where to go when I return to the continent one day (soon, I hope!).
It is a beautiful area Bama. Imagine all those small towns and villages you could research. So many ancient buildings with stories to tell. I hope you get there one day soon.
Wow, what a great post. Hard to pick which town seems most perfect for me but I think I have it: San Casciano, with great Chianti, restaurants, the extra virgin olive oil you mention as well as the organic foods. And I would have to stay in the hotel you mention, too, with an entire suite and the views? Sounds like just what we’re looking for!
San Casciano is a fabulous little village. The hotel’s ratings and reviews match our experience. Such friendly service on top of it all. I will say the view from our room was into the village and not the rolling hills of Tuscany. I just wanted to be clear about that part. It’s very hard to go wrong in Tuscany but this one is great value for the price.
Sue, I’m sure this très informative post will be very popular with Tuscany-bound travelers. The kitchen photo in Sette Quece is so charming and looks like so many places we’ve stayed. As you know, we’re all about apartments vs. hotels and this looks and sounds like a great one. Great post. ~James
James we have a dream of returning to Tuscany once Dave is retired and plunking ourselves down for a month. An apartment setting is exactly what we will be looking for. We definitely thought about that during our stay in wee San Casciano. Thank you for the kind feedback. In all honesty the post came about when I finally got tired of looking up the information over and over for people who asked. 🙂
Tuscany is a really breathtaking region. I would love to stay in Cortona as it seems so charming. When’s the best time of the year to explore this area?
Agness it can be quite busy in July and August however there may be more activity in the towns such as festivals as well. I would look at May-June and Sept-Oct. Outside of those months you would want to check that restaurants and smaller hotels actually stay open in the off season. A long winded answer to try to hit shoulder season.
We are headed to Rome this fall, but may make another trip back to Italy in the next few years, so will come back to this post if that is the case.
Have a fabulous time in Rome Amy. What a city and so much to see and do. Thanks for keeping this reference in mind for future visits.
Although we loved our entire time in Italy, staying in a farmhouse in the Tuscan countryside was probably one of our favorite stays. Thanks for giving me ideas for another visit, which we hope to do one day.
I’ve always had a love for hill stations, but never got to explore beyond the place I live. Thanks for this wonderful compilation.
A pleasure to share. This post remains one of our most popular. It seems many people dream of beautiful Italian hilltop towns.