Last updated on January 10, 2024 by Stefano Ferro, founder of MEL365, following extensive travelling in Tuscany

Where to Stay in Chianti: Insider’s Guide to the 7 top areas

Wondering where to stay in Chianti for the best taste of Tuscany? Look no further! This guide is designed to help you discover the best places to stay in Chianti, where the charming Italian lifestyle is as popular as the renowned wine.

The Chianti region caters to a diverse range of interests, from history and food to wine and nature, ensuring there’s something for everyone to enjoy.

Our suggestions will take you through medieval towns, peaceful vineyards, and even traditional farms or ‘Agriturismo‘, providing you with an unforgettable experience on a handy map and a table to compare all the destinations.

But let’s dive into it

Cypress landscape of Tuscany on a foggy morning
Cypress landscape of Tuscany on a foggy morning

Where to Stay in Chianti – Let’s compare the best areas

Here is a table that compares the 7 best places to stay in Chianti. It’s a very handy reference, perfect to have a quick overview of the region and understand what could work better for your own holiday.

Click on the area name to read a full description, including all pros, cons, main attractions and the best restaurants and wine bars. Swift left or right on a mobile to view all columns.

AreaSuggested forProsConsBudgetAccessibilityAttractionsRestaurantsFamiliesNightlifeCharacter
ImprunetaBest town to stay in Chianti for familiesFamily-friendly, quiet, close to FlorenceLack of nightlifeMid-rangeGood, especially with a carTerracotta fornaci, annual Grape FestivalExcellentExcellentPoorTraditional, artisan
San Casciano Val di PesaBest town to stay in Chianti for the wineRich in history, fantastic wine cultureNot the most budget-friendlyHigh-endGood, but easier with a carMonastery of Santa Maria del PratoExcellent, especially for wineGoodModerateHistoric, wine-focused
Tavarnelle Val di PesaBest town to stay in Chianti on a budgetAffordable, stunning landscapesLimited attractions in townLowGood, both car and public transport Natural parks and landscapesModerateGoodNoneNatural, tranquil
Greve in ChiantiBest town to stay in Chianti for first-time visitorsVibrant atmosphere, great food scene, charming central squareCan be busy in peak seasonMid-to-highGood, but easier with a carThe central square, numerous wineriesExcellentModerateModerateVibrant, food-focused
Radda in ChiantiBest town to stay in Chianti for romantic couplesPicturesque medieval village, romantic settingNo nightlife, poor public transportationHigh-endRequires a carVineyardsExcellentModerateNoneCharming, romantic
Castellina in ChiantiBest town to stay in Chianti for historyRich history, lovely sceneryCan be busy during peak seasonMid-to-highRequires a carThe fortress, Archaeological Museum of ChiantiExcellentModerateNoneHistoric, picturesque
AgriturismoBest place to stay in Chianti for natureUnique accommodation, serene surroundingsFar from towns and centresVariesRequires a carNature and local farm experiencesExcellent (local food)ExcellentNoneRural, authentic
Best areas to stay in Chianti

Siena and Florence are two other great places to stay in Tuscany to be based and organise one or two day trips to the Chianti area.

I personally recommend renting a car in Tuscany if you want to explore the Chianti region. Technically it can be done also with public transportation, but besides taking 3-4 times more, you may end up with the impossibility to visit some of the medieval villages or wineries around your stay (taxis are rare, especially in peak season).

Map of where to stay in Chianti
Map of where to stay in Chianti
Chianti classico in spring
Chianti classico in spring

Impruneta

🌎 Best place to stay in Chianti for families and art

Pros: Peaceful atmosphere, family-friendly, renowned for terracotta production, close to Florence.

Cons: Limited nightlife, few late-night bars.

Attractions: Fornace Terrecotte Masini, the Basilica of Santa Maria, and the annual Festa dell’Uva.

Suggested Restaurants and Cafes: Diadema Wine Bar & Restaurant, La Loggettina, Ristorante Il Battibecco, Gelatilandia.

The question of where to stay in Chianti often depends on your particular interests, and if you’re fond of art and prefer a quieter stay suitable for a family, Impruneta could be just the spot for you.

This small town dates back to the Etruscan times with its terracotta tradition. And it is still producing some amazing pieces of art, today world-famous.

Of course, once in Impruneta, you should check out one of the many fornaci, where they make famous terracotta products. One place I suggest is the laboratory of Terrecotte Masini, just an easy stroll from the centre of town.

This serene town is ideal for families, providing a calm and relaxed environment that is a refreshing escape from the fast-paced and crowded cities.

The narrow, cobbled streets of Impruneta are perfect for leisurely strolls, and the town’s proximity to Florence makes day trips to explore the art and history of the Tuscan capital easy and convenient.

For the foodies, Impruneta offers an authentic taste of Tuscany. Try the Bistecca alla Fiorentina at Ristorante Il Battibecco, or the Peposo (a local beef stew) at the Diadema Wine Bar. And don’t forget to pop into Gelatilandia for Italian gelato.

Let’s jump to the drawbacks of this option. The quiet charm of Impruneta might be a pro for some, but for those looking for some sort of nightlife and bars open late into the night, it might not be the best fit. The nightlife here is low-key, focusing more on relaxing evenings and quiet nights.

However, if a peaceful stay amidst beautiful terracotta and close to the Tuscan capital sounds like your cup of tea, Impruneta might just be one of the best places to stay in Chianti.

Here are 2 great hotels in Impruneta

Bellavista Impruneta($$): Charming hotel, breathtaking views, modern facilities, friendly staff. Immaculate rooms. Authentic Tuscan cuisine. Value for money.

B&B il Connubio ($$): Perfect retreat with clean rooms, fantastic kitchen, and friendly staff. Secluded yet accessible.

Amazing spring landscape with green rolling hills and farm houses in the heart of Chianti in morning
Amazing spring landscape with green rolling hills and farmhouses in the heart of Chianti in the morning

San Casciano Val di Pesa

🌎 Best place to stay in Chianti for the best wine in the world

Pros: Immersed in history, rich wine culture, picturesque countryside, and numerous wineries.

Cons: Not the most budget-friendly option, fewer attractions than in larger towns.

Attractions: Pieve di Santa Cecilia a Decimo, The Museum of San Casciano, Cantina Antinori

Suggested Restaurants and Cafes: Ristorante Nello, Antica Fiaschetteria del Chianti, Antinori nel Chianti Classico

The question of where to stay in Chianti becomes a no-brainer for wine enthusiasts and history buffs when San Casciano Val di Pesa comes into the picture.

You will find this town nestled between rolling hills and vineyards. It’s a town full of history and with huge wine culture, we are in the heart of Chianti after all.

The town offers a range of wineries that produce some of the best vintages in Italy.

The Cantina Antinori is a particular favourite, a wine estate that has been producing high-quality wines for more than 600 years. A visit here is an absolute must for any wine lover.

After all, Antinori has been named World’s Most Admired Wine Brand in 2023, thanks to its amazing futuristic winery architecture and its well-known and prized wines, as the Super Tuscan label.

The history of San Casciano Val di Pesa goes back to the medieval era, and you will quickly notice that in the architectural style around town.

The Pieve di Santa Cecilia a Decimo (church) is a particular gem, standing majestically amidst the Tuscan hills.

Similarly, the Museum of San Casciano provides a fascinating look at the town’s history and culture, with unique pieces of art.

San Casciano Val di Pesa is also home to some truly incredible food. Ristorante Nello is a standout choice, with its classic Tuscan dishes and extensive wine list.

Alternatively, Antica Fiaschetteria del Chianti offers a mouth-watering selection of regional dishes.

Finally, a must is to have either lunch or dinner at Antinori, however, book your table well in advance. The locally produced wines are of course a winner.

However, as perfect as it might seem, San Casciano Val di Pesa isn’t for everyone. It’s not the most budget-friendly town in Chianti, with the premium wines and fine dining experiences reflecting a price tag to match.

But if you are into history and good wine, there’s no better place to be. This town truly embodies the essence of Chianti, making it one of the best places to stay for a genuine Tuscan experience.

Here are 2 great hotels in San Casciano Val di Pesa

Palazzo Tempi ($$-$$$): Charming blend of historical elegance, modern comfort, and ideal location. Needs minor improvements for perfection. Great value for money.

Villa Il Fedino ($$$): Exquisite 14th-century villa offering luxurious comfort, impeccable service, and a stunning outdoor pool. Truly a Tuscan gem

Amazing Tuscany landscape with green rolling hills, olive trees, vineyards and farm houses
Amazing Tuscany landscape with green rolling hills, olive trees, vineyards and farmhouses

Tavarnelle Val di Pesa

🌎 Best place to stay in Chianti on a budget

Pros: Affordable accommodation options, breathtaking natural landscapes, tranquil atmosphere, and proximity to nature.

Cons: Limited local attractions, reliance on natural beauty over cultural or historical landmarks.

Attractions: Badia di Passignano, Santa Lucia al Borghetto Church.

Suggested Restaurants and Cafes: Osteria La Gramola, Pasticceria La Fiorentina, Ristorante La Torre, La Fornace

If you’re deliberating on where to stay in Chianti that perfectly balances cost and beauty, Tavarnelle Val di Pesa will definitely charm you.

This tranquil town is a haven for budget travellers and nature lovers, showcasing the rustic charm of Tuscany without putting too much strain on your wallet.

The landscape surrounding Tavarnelle Val di Pesa is a sight to behold. It’s a beautiful and typical Tuscan countryside made of vineyards, olive groves, and panoramic views of the rolling hills.

A trek to Badia di Passignano, a historic abbey nestled amidst these landscapes, is a truly memorable experience.

For lunch, you should reserve a table at the Ristorante La Torre, just outside town. Besides the fine dining experience, you will experience one of the best views of the Chianti region.

Osteria La Gramola offers an unforgettable culinary experience with its locally sourced ingredients and innovative interpretations of traditional dishes.

For something a bit more casual but equally delightful, La Fornace serves up local favourites that will keep you coming back for more.

However, it must be said that Tavarnelle Val di Pesa is a bit limited when it comes to local attractions. The town is quieter than some of its neighbours, making it a peaceful retreat rather than a bustling tourist hub. If you’re seeking a serene getaway amidst nature, this town could be the perfect fit.

If, however, you’re after a more active holiday filled with sightseeing and cultural experiences, you might find Tavarnelle Val di Pesa a little lacking.

Here are 2 great hotels in Tavarnelle Val di Pesa

Via Naldini n 61($): exceptional service, immaculate rooms, and a prime location.

Cris&Giuli House ($): clean and comfortable stay at a great price

Exploring the Chianti area
Exploring the Chianti area

Greve in Chianti

🌎 Best place to stay in Chianti for first-time visitors and foodies

Pros: Vibrant atmosphere, incredible food scene, charming central square, and a wealth of wine-tasting opportunities.

Cons: Can become crowded during peak tourist season, making for a slightly less peaceful experience.

Attractions: Montefioralle, Chianti’s smallest historic centre, Wine Museum, and the charming Piazza Matteotti.

Suggested Restaurants and Cafes: Enoteca Ristorante Gallo Nero, Antica Macelleria Falorni, Il Vinaino Di Greve in Chianti, Pasticceria Chianti.

When pondering where to stay in Chianti, Greve often emerges as a top contender, especially for first-time visitors and foodies.

This lively town brims with Italian charisma and offers an unforgettable gastronomic journey through the best of Tuscan cuisine.

Greve boasts a prime location, right in the heart of the Chianti region, with easy access to several of the best attraction in Chianti.

Yet, the town itself is a treasure trove of attractions. Montefioralle, one of Chianti’s smallest historical centres, is just a stone’s throw away and promises a fascinating journey back in time.

The Wine Museum in Greve is another must-visit, especially for wine enthusiasts keen to delve into the region’s rich viticultural heritage.

Greve’s central square, Piazza Matteotti, is a delight to explore. Framed by arcaded walkways housing various shops and eateries, this charming piazza pulses with life and energy.

Foodies are sure to find their paradise here, with restaurants and cafes dishing up everything from hearty pasta to gourmet creations.

At Enoteca Ristorante Gallo Nero, you can savour traditional Tuscan dishes paired with a broad selection of local wines. For a taste of Chianti’s renowned cured meat and local cheeses, make a beeline for the Il Vinaino Di Greve in Chianti, a historic bistro that’s been serving up these local specialities for centuries.

So, what is the drawback of staying in this town? The town can become quite crowded during peak season, and while this adds to its vibrancy, it may detract from the peaceful Tuscan experience some visitors seek.

Despite this, Greve remains one of the best towns to stay in Chianti, particularly for those keen on a dynamic, flavour-filled Tuscan adventure.

Here are 2 great hotels in Greve in Chianti

Manto Palace ($$): 2BR Apartment. Charming and spacious, comfort, clean, superb location, and stellar hospitality. Excellent value for money

Apartment Piazza Matteotti ($$): Charming, traditional apartment in an excellent location. Steep stairs and occasional noise may be an issue, but overall good value.

Vines growing in rural vineyard near Radda in Chianti
Vines growing in rural vineyard near Radda in Chianti

Radda in Chianti

🌎 Best place to stay in Chianti for romantic couples amidst vineyard-covered hills

Pros: Picturesque medieval village, romantic setting, breathtaking views, charming architecture, vineyard-covered hills, perfect for couples seeking a romantic getaway.

Cons: Lack of nightlife, poor public transportation, far from both Siena and Florence.

Attractions: Propositura di San Niccolò

Suggested Restaurants and Cafes: La Bottega di Giovannino, Le Panzanelle, Bar Dante.

Deciding where to stay in Chianti can be quite a task given the array of charming towns that fill the region.

But if you’re a couple looking for a romantic escape, you’ll struggle to find a setting more idyllic than Radda in Chianti.

This picturesque medieval village set atop a hill is defined by its vineyard-covered surroundings, offering breathtaking views that will leave you and your partner enchanted.

The romance in Radda extends beyond its landscapes. Strolling hand-in-hand through its cobbled streets, you’ll come across charming historic architecture that further enhances the town’s allure. The standout landmark is the Propositura di San Niccolò (church), boasting a beautiful rose window.

Food lovers are not left out in this small town. Radda offers a range of restaurants and cafes that serve mouth-watering Tuscan cuisine.

La Bottega di Giovannino is a popular spot, known for its regional dishes and cosy atmosphere.

Le Panzanelle, although a 10-minute drive from the town, is another must-try for their delectable homemade pastas and traditional Chianti-style dishes.

Lastly, for a relaxing drink after a day of exploring, head to Bar Dante, a welcoming spot that serves a variety of local wines.

As one of the best places to stay in Chianti, Radda does come with some downsides. The nightlife is virtually non-existent, and public transportation options are also limited. Plus, it’s quite a distance from both Siena and Florence.

Despite these, the charm of Radda lies in its tranquillity and beauty, making it a perfect choice for couples looking to disconnect and enjoy each other’s company.

Here are 2 great hotels in Radda in Chianti

Dolcevita Chianti Apartments ($$): Exceptional cleanliness, comfort, and location. Well-equipped for self-catering. Hosts provide top-notch service.

Relais Vignale & Spa ($$$): Charming historic villa with panoramic views, exceptional staff and facilities

Chianti Vineyard in the Tuscan Hills on a Summer Morning
Chianti vineyard in the Tuscan hills on a summer morning

Castellina in Chianti

🌎 Best place to stay in Chianti for the history enthusiast

Pros: An impressive fortress, rich history, and picturesque scenery.

Cons: Can get very crowded during the peak season, and limited public transportation options.

Attractions: Via delle Volte, Rocca di Castellina, Archaeological Museum of Chianti Senese, Church of San Salvatore.

Suggested Restaurants and Cafes: Il Fondaccio dai Dottori, Albergaccio, Il Re Gallo.

When deciding where to stay in Chianti, history enthusiasts would undoubtedly find Castellina an appealing choice. This charming town is rich in history and boasts an impressive fortress that will undoubtedly inspire awe.

As you traverse its medieval streets, you’ll be treated to stunning views of the surrounding landscapes, amplifying the allure of this lovely town.

There are a number of attractions in Castellina in Chianti that you don’t want to miss. First, take a stroll down Via delle Volte, an intriguing medieval street that offers charming views of the town.

Don’t miss the opportunity to visit Rocca di Castellina, an imposing fortress that provides panoramic views of Chianti’s wine-growing regions.

Finally, explore the Archaeological Museum of Chianti Senese. There is a small entrance fee (5 Euros), and besides the boutique collection of regional artefacts, you will get to enjoy the magnificent view over the Chianti region from the upper level.

Surely you will have plenty of options when it comes to eating out in Castellina. At Il Fondaccio dai Dottori, you’ll be treated to delicious Tuscan cuisine in a cosy setting.

Albergaccio is another great option if you’re a fan of local dishes and excellent wines. For fresh pasta lovers, a visit to Il Re Gallo is a must.

Despite being one of the best places to stay in Chianti, Castellina does have its drawbacks. It can get quite busy during the peak season, which might not appeal to everyone.

Additionally, public transportation is not great in this corner of Tuscany and I would personally suggest renting a car in Italy to visit most of the Chianti region.

With its historical charm and beautiful scenery, Castellina in Chianti offers an unparalleled experience to history buffs.

My personal tip here. Remember to book a table for lunch, because restaurants can be quite busy, especially in peak season (May-October). This is less of a problem for dinner when most of the day trippers have left the town.

Here are 2 great hotels in Castellina in Chianti

Mariani Bed&Breakfast ($$): Charming B&B with exceptional staff, clean rooms, and hearty breakfast. Great value for a serene Chianti experience.

San Martino – Casa Landi ($$$): Charming Tuscan experience, authentic ambience, friendly staff, great views, great pool

Chianti is all about nature and wine
Chianti is all about nature and wine

Agriturismo

🌎 Best place to stay in Chianti for nature lovers

Pros: Scenic natural surroundings, direct proximity to wineries, and authentic local food experience.

Cons: Usually located far from town centres and lacking in public transportation options.

Attractions: Wine tours, Cooking classes, Olive oil tasting, Hiking in nature.

Suggested Restaurants: Typically, meals are prepared and served within the Agriturismo.

The agriturismo is a great place to stay for families and nature lovers
The agriturismo is a great place to stay for families and nature lovers

If you are wondering where to stay in Chianti for a different and unique experience, the Agriturismo may be your answer. This type of accommodation will put you directly in touch with nature.

But what is really an Agriturismo? These are typically farms-turned-rustic accommodations giving you a chance to stay amidst vineyards and olive groves while relishing home-cooked meals made from locally-sourced ingredients. I am personally a fan of this type of accommodation, so easygoing and such a great value for money.

What makes Agriturismos one of the best places to stay in Tuscany, and even more so in Chianti, is the sheer variety of experiences they offer.

Love wine? A good number of Agriturismo are actually wine producers or winemakers, which means you won’t have any trouble joining a customised wine tour of a winery.

And what about the food? Many Agriturismos offer lunch and dinner made from local products and you could even join cooking classes where you can learn to prepare traditional Tuscan dishes under the guidance of a local chef.

While the tranquillity of staying on a farm might be a big draw, it’s worth noting that Agriturismos are typically located far from town centres, which can be a downside for some.

Getting around can be challenging as public transport is often lacking. Therefore, hiring a car in Tuscany is highly recommended when staying at an Agriturismo.

Despite the minor inconveniences, if you love nature, crave an authentic food experience, and don’t mind being a bit out of the way, an Agriturismo can be an excellent choice.

Here are 2 great Agriturismo in the Chianti region

Agriturismo Corte Di Valle ($$$): Authentic Tuscan experience with delightful staff, exquisite homemade wines, and breathtaking views. Perfect countryside retreat.

Castello Di Gabbiano ($$$$): Immersive Tuscan experience in a historic castle; stunning views, superb facilities, friendly staff, intermittent WiFi

Typical rural landscape in the region of Chianti
Typical rural landscape in the region of Chianti

FAQ – Where to stay in Tuscany

What is the best town to stay in Chianti for wine tours?

San Casciano Val di Pesa is a great option due to its rich wine culture and abundance of wineries. You can also think to stay in Siena and take a day tour from there

I’m travelling on a budget. Where should I stay in Chianti?

Consider Tavarnelle Val di Pesa. It offers affordable accommodations and is surrounded by stunning natural landscapes

Which is the best place to stay in Chianti for a romantic getaway?

Radda in Chianti, with its charming architecture, beautiful views, and vineyard-covered hills, makes it a perfect spot for couples.

I’m looking for a unique accommodation experience in Chianti. Any suggestions?

Try an Agriturismo! These farm-stay experiences offer serene surroundings, beautiful landscapes, and the opportunity to learn about local agriculture.

Should I rent a car to visit the Chianti region?

Although you can visit the major town with public transportation, I highly suggest renting a car in Tuscany and exploring the region at your own pace. So many hidden corners will come up along the road trip

Stefano Ferro - MEL365.com Founder and Editor

About the Author

Stefano is a seasoned travel expert and the visionary founder of MEL365.com, a leading travel website with traffic across 6 continents. With a rich background in the travel industry, Stefano spent four pivotal years at Amadeus Travel Distribution System, gaining invaluable insights into travel technologies and distribution.

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