The 7 Best Villages in Tuscany

The 7 Best Villages in Tuscany Best villages in Tuscany

With medieval Italian hill towns overlooking a stunning landscape of rolling hills, cypress trees, and luw green vineyards, a trip to Tuscany can’t help but feel like somewhere magical. If the scenery weren’t enough, there’s also the local wine and food with specialties like the Florentine T-bone steak, Cacciucco fish stew, and the famous Chianti wine. To get the best recommendations on Tuscany, I’ve teamed up with some great female travel bloggers who also adore Tuscany to create our top 7 list of the best villages in Tuscany. So whether you are a foodie, history buff, luxury traveler, or outdoor enthusiast, we’ve got you covered with our complete guide to the best villages and most beautiful towns and cities in Tuscany! 

Some links in this article may contain affiliate links which I may earn a small commission from at no extra cost to you. 

Map of Tuscany Towns to Visit  

Map of tuscany towns

For tips on what to pack for Italy, click here.

Vinci, Tuscany

Written by Janelle of My Vacation Pants

Vinci Italy

Italy is just one of those places that you dream about visiting your whole life and it definitely lives up to your dreams, but nothing quite prepared me for adorable charm and beauty of the small Tuscan village of Vinci, yep, the one Leonardo is from.

Things to do in Vinci

We stayed in an agroturismo right outside the city walls called Tenuta Le Colonie. This particular agriturismo was a farm where you stayed in a little villa with a full kitchen and multiple bedrooms.  It was a steal at $79 USD a night.  One of the cheapest places we stayed in our three-week stay in Italy.

On our full day, we went into the city walls and walked the streets and took it all in.  You almost felt like you were back in Leonardo’s time.  I don’t think the city has changed much in the last few centuries. We went to the Leonardo Di Vinci Museum and learned all about his life, art, and inventions.  The highlight of the museum was walking up to the top of the clock tower and hearing the bells ring out across the countryside.

For those of you who want the foodie experience check out Il Ristoro Del Museo.  Walk downstairs to a small dining room that sits on the wall of the city.  The homemade pasta and sauces were delicious and the couple that owned the restaurant were exquisite people.  Even though there were eight of us all together they had no problem making room for us.

Seriously, I know that there are many famous places to visit in Italy, but you won’t be disappointed if you stop in this fantastic little Tuscan town.  I still dream about those rolling hills…and the pasta.

Check out our tips to travel with a family on a budget at and follow our travelogue at 

Tavarnelle Val di Pesa, Tuscany

Written by Diamond of Ink For Miles

Tavarnelle Val di Pesa - Towns in Tuscany

You know the romanticized version of Italy we’ve built up in our heads with the rolling green hills, vineyards, charming old Tuscan homes, cobblestone paths and fresh olive oil in every restaurant? Yes, the picture that is forming in your mind right now…that’s Tavarnelle Val di Pesa.

Things to do in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa is a beautiful little slice of Italian countryside located 30 minutes away from Florence. Throughout history, as far back as the Middle Ages, Tavarnelle has been a pit-stop for travelers going to and from Siena and Florence. It was where people stopped to get some rest and a hot meal before continuing on their way. Even now, you probably never heard of Tavarnelle but I’m sure you know Siena and Florence well. Tavarnelle may never fully shake off its reputation as a pit stop but thankfully it still remains a hospitable, beautiful place.

Tavarnelle may not have Michelangelo’s David, but what it does have is the opportunity for guests to indulge in free wine tastings. Borgo di Cortefreda is one such hotel where the public is allowed to sample their collections of wines, cheeses, jams and extra virgin olive oil.

After a long day eating your way through Tavarnelle you can rest your head in a charming little hostel called Ostello del Chianti. Between the delicious samples of the region and the kind, welcoming townspeople, you’ll love every minute you spend in Tavarnelle Val di Pesa. Happy Travels!

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San Gimignano, Tuscany 

Written by Shweta of Zest In A Tote

San Gimignano, one most beautiful villages in Tuscany

Do you want to be transported to the medieval era? Feel what it would be like to walk past stone towers, ancient buildings, and rustic architecture. San Gimignano, a town 60 km away from Florence is the place for you.

Things to do in San Gimignano

The first look of those stone towers rising atop a hill, and you will realize why San Gimignano was put in UNESCO’s World Architectural Heritage.

There is one main road that cuts through the entire town and it is packed with tourists and boutique stores and lovely cafes.

Like any other beautiful village in Tuscany, San Gimignano has a central square – Piazza del Duomo – where you can visit the Cathedral and see the various medieval towers. The only tower open to the public is the Torre Gross. This stands the tallest at 54 meters (177 feet) in height and offers panoramic views of the Tuscan landscape.

If you are planning just a day trip here, my suggestion would be to relax, soak in the pleasant vibes, eat lots of gelatos, drink some wine, try wild boar salami at a gourmet food store and do window shopping at the myriad leather, ceramic and food stores. I got tempted to buy a lovely pair of leather sandals.

For more on San Gimignano, check out Shweta’s blog or follow her on Instagram!

Volterra, Tuscany 

Written by Daniela of Ipanema travels to…

The Italian hill town of Volterra

Volterra is one of those beautiful towns that you can’t miss when traveling in Tuscany. It’s standing there on the top of the hill, surrounded by the old Etruscan city walls, inviting you to discover its charm and historical treasures.

Things to do in Volterra

Volterra was an important place during the height of the Etruscan civilization (9th – 3rd century BC). You can learn more about the Etruscans (who were they, how they lived) at the Gurnacci Etruscan Museum, which I highly recommend. The Romans that followed the Etruscan, have also left they mark in Volterra. Today, you can visit one of the biggest and best preserved Roman theatres exactly in Volterra.

The historic city center is a real gem of medieval architecture with the impressive Palazzo dei Priori – the oldest town hall in Tuscany – built between 1208 and 1257. Walk around and get lost in the tiny streets and try to picture how life was there when Volterra was flourishing as one of the city-states before it was conquered by Florence and included in the Grand Duchy of Tuscany in the 15th century.

Volterra offers one of a kind dining experience at the Medici Fortress – the so-called Cena Galeotta – “dinner in prison”. The fortress functions as a prison and you can book a dinner there. The inmates will be cooking and serving your meal as part of a project for their re-integration and education before while finishing their sentence.

Read Daniela’s complete guide to all tourist attractions in Volterra on her blog and follow her on Instagram!

Castellina in Chianti, Tuscany 

Nestled in the Tuscan rolling hills is one of the best villages in Tuscany… Castellina in Chinati. Here, traditional old stone farmhouses stand between vineyards whose grapes produce the well known Chianti wine. 

Castellina in Chianti one of the most beautiful towns in Tuscany

Things to do in Castellina in Chianti

When searching for the most beautiful towns in Tuscany for our honeymoon, Jugo and I chose to visit Castellina in Chianti. We stayed at a B&B called Castello di Fonterutoli which is located in a medieval hamlet with vineyards and a winery of its own which has been kept in the Mazzei family since the 11th century. We had a lot of fun going on a wine tour and sampling their Chianti wine. There are also many other vineyards close by including:

Vineyards in Tuscany

If wine drinking isn’t your thing, check out some of the sites. Take a walk in Via Delle Volte which is a stone-walled tunnel that was used in medieval times to protect the town. It is located above the town which gives you great views of the valley. Inside are local boutique shops and cafes. Another option is to visit Rocca di Castellina, a fully restored castle that sits on top of the hill with great city views. Or if you prefer ancient ruins, visit the Etruscan Tomb which dates back to the sixth century.

Lastly, stop by local tavernas and eat some pizza and pasta! Talk with locals to find the best places to or visit any place that’s packed with locals. Jugo and I also enjoyed visiting local bakeries and shops to pick up supplies up for a picnic. The scenery is so beautiful,  you can pretty much stop for a picnic anywhere!

Pienza, Tuscany 

Written by Katy of Untold Morsels
Best towns in Tuscany, Pienza.
In a region blessed with so much beauty, Pienza is a town that stays with you long after you left.
Sitting high on a hill in southern Tuscany, the town overlooks the Val D’Orcia and there are spectacular 
views at almost every turn.

Things to do in Pienza

Pienza is one of the most beautiful towns in Tuscany whose cobbled streets lead to pretty piazzas, an impressive Duomo, and a grand palazzo. As you wander along the streets, notice their love-themed names like Via del Bacio (Kiss Street).
This pretty town is one of those places where the best activity is to wander and soak up the atmosphere but there are a couple of must-see things to do in Pienza. Palazzo Piccolomini was the home of two popes and is worth a visit to discover more about the town’s history, an impressive garden as well as the best views of the surrounding countryside. You should also take a peek inside the impressive cathedral next door.
Pienza is well known for pecorino cheese and many people go there just to taste and take home the celebrated sheep’s milk cheese. If you go to Pienza in the fall you can take part in the town’s annual harvest festivals. The most famous of these is the cheese rolling event in late September.
For more on small towns in Italy check out Katy’s blog or follow her on Twitter!

Cortona, Tuscany 

Written by: Alicia of Miles Less Traveled

Medieval towns in italy - Cortona, Tuscany

Made famous in the early 2000’s by the romantic film Under the Tuscan Sun, Cortona is the picturesque town everyone imagines when they begin planning a trip to Italy. Tucked into the majestic Tuscan hillside, the winding, narrow cobblestone streets ooze with charm. It is a town of history, leisure, and excellent food.

Things to do in Cortona

Take in the countryside on a vineyard tour of the surrounding regions that produce some of the best known and loved wines in the world. Or, spend time simply wandering from restaurant to restaurant, taking in the traditional and old architecture along the way that makes this town the beauty that it is.

For an unforgettable meal, have lunch at Fiaschetteria Fett’unta. Order a sampling of the crostinis, a bowl of traditional Ribollita soup, or freshly shaved truffle over handmade pasta.

For a place to stay look no further than Le Bifore, where the property manager Laura will treat you to a rotating selection of delightful homemade cakes for breakfast. If you upgrade to a suite, get the room with views overlooking the valley, they are truly incredible.

Follow Alicia on Instagram!

The Best Cities to visit in Tuscany

If you are looking for places in Tuscany with more things to see and do, consider adding a couple cities to your itinerary. If you are flying into Tuscany, Lucca is just a 25-minute drive away from the Pisa Airport while Siena is around an hour away from the Florence Airport. 

Lucca, Tuscany

Written by: Jessica of The Belle Voyage

Lucca, Tuscany

Situated in Northern Tuscany, Lucca is a well-preserved gem that is one of Italy’s most charming cities.  Located close to other visitor favorites such as Florence and Pisa, Lucca makes for a perfect base if you’re spending a few days in Northern Tuscany. 

What to do in Lucca

There are a few must-dos when visiting Lucca.  Rent a bike and cruise the medieval walls that surround the city, and lunch in the oval-shaped Piazza Anfiteatro.  Wander the narrow cobblestone streets, and boutique hop on Via Fillungo, Lucca’s main shopping street.  Climb to the top of Guinigi Tower for a spectacular view of Lucca’s red rooftops, and to see the sky-high hanging garden.  And if you’re spending the night in Lucca, you absolutely must check out a Puccini concert.  An Italian opera composer, Giacomo Puccini was born in Lucca, and the city honors his legacy by putting on a nightly concert featuring his pieces.  Hearing the opera classics in such an authentic setting is a travel memory you won’t soon forget.

Follow Jessica on Instagram @thebellevoyage!

Siena, Tuscany 

Written by Rachael of Bee Anything But Boring

Siena, Tuscany 

When exploring Tuscany, Siena is a town you cannot miss! In fact, the city center was declared a UNESCO World Heritage Site and is arguably one of Italy’s most unique medieval towns.

Things to do in Siena

At the center of Siena is Piazza del Campo, which is where the world-famous Palio di Siena horse race occurs twice each summer. Depending on when you visit Siena, you may find the square covered in clay in preparation for the event.

For stunning views of the city, you can climb up 400 steps to the top of the Torre del Mangia. This bright red tower 102 meters above the square, is the tallest symbol of Siena.

You also can’t miss visiting Siena’s Duomo, a beautiful gothic style church, decorated inside and out in white and dark green striped marble and mosaics. If you have previously visited the Duomo in Florence, you may be surprised at the striking differences between the two.

Finally, like in most Italian towns, the food, the wine, and the gelato speaks for itself!

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Now it’s time to start planning your trip to the best villages in Tuscany! Which village are you most excited to visit? Comment below. 


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11 thoughts on “The 7 Best Villages in Tuscany

  • I love Italy! We honeymooned on the Amalfi Coast for a week, and I keep saying on our next trip to italy we should explore Tuscany! This has given me serious wanderlust…

    • Hi Erin, thanks for your comment. I’ve never been to Amalfi but from the pictures I’ve seen, it looks like an amazing spot for a honey moon. Tuscany is definitely perfect for a romantic trip for couples so maybe you should return to Italy for a wedding anniversary!

  • Wow these towns look magical!! San Gimignano is the only one I’ve been to, and it might be one of my favorite towns in Italy! (They have some bomb gelato, so that already puts them way up towards the top of the list lol.) Can’t wait to read more of your posts!

  • I love this post. I immediately started dreaming of the rolling Tuscan hills. I can’t believe that I have been to Italy three times and have yet to include Tuscany. I have to change that!!

    • Hi Michelle, thanks for your comment! Tuscany is pretty amazing and definitely worth a fourth trip 😉

  • Take me back to Italy!!! This post gave me the serious feels as I did a semester abroad in Florence and LOVED Tuscany! I missed some of these so I would love to go back and do this entire route!

    • Hi Megan, thanks for your comment. Wow! That’s amazing that you got to spend a whole semester in Florence! I was only there for a week but definitely need to go back and spend a lot more time exploring and tasting there 🙂

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