Where to Stay in Chianti - Best Bases & Hotels
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The Chianti region, the swath of rolling hills between Florence and Siena in the heart of Tuscany, serves up some of the most romantic and soothing scenery in Italy, if not the world.
Stone villages and ocher-hued towns crown the hilltops and are nestled in river valleys. Villas and manor houses are tucked away at the end of cypress-lined drives amid acres of vineyards and the towers of centuries-old castles rise above deep forests of chestnut and oak. Not only are the landscapes timeless and transporting, but they also produce some of the world’s most acclaimed wines.
Whether your idea of heaven is drinking excellent wines or simply drinking in soothing views, you’d be hard-pressed to find a more beautiful and welcoming part of Italy, and that’s saying a lot.
So, no matter where you choose to stay in this wonderful little place, I think you’ll have a great time. But I’ve of course got my own preferences and there are spots that I like more than others, so I’m going to dig into all of that throughout this guide.
Toward the end of the article I’ve recommended a bunch of my favorite hotels/lodgings in the area, but before getting to that I want to cover some of the essential things for you to consider as you try to work out where is best for you.
Let’s jump in.
Table of Contents
Where is Chianti and what is it
Before we get into anything else, let’s just quickly cover the very basics: first, I’ll explain where Chanti is in Tuscany, and then what exactly it is.
Chianti is a hilly, largely rural area best known for its vineyards and olive groves that lies between the cities of Florence (to the north) and Siena (to the south).
The towns of Chianti are all within easy reach of both Siena and Florence, and of one another. To give you an idea, the town of Greve is about 20 miles south of Florence and 25 miles north of Siena. It won’t take you much more than half an hour to reach it from either city.
As for what Chianti is, I think the best answer is that it’s a small largely agricultural sub-region of Tuscany that’s famed for its Chianti Classico Wines which are produced from the local Sangiovese grape.
This isn’t actually an official administrative area of any kind, but it’s generally thought to encompass these eight towns:
Barberino Val d’Elsa
San Casciano in Val di Pesa
Castelnuovo Beradenga
Castellina in Chianti
Gaiole in Chianti
Greve in Chianti
Panzano in Chianti
Radda in Chianti
Things to consider when planning your visit
Poggio Amorelli winery in Castellina in Chianti. Photo: Ray in Manila, CC BY 2.0, via Wikimedia Commons
Chianti is small
The region is about one-fourth the size of Rhode Island, the smallest U.S. state. It’s only 30 km (18 miles), or 35 minutes by car, from Greve, in the north of the region outside Florence, to Castellina in Chianti, in the south, outside Siena. This means that no matter where you stay you’ll be well located to visit the rest of the region, and other parts of Tuscany as well.
It’s the experience, not an exact location, that matters
Given the relatively small size of the Chianti region, a particular town or neighborhood, big factors in pinning down accommodations in many places, are not a major consideration when choosing a place to stay in Chianti. This frees you up to choose the type of place you want to stay rather than where it is, and there are many appealing options.
You might want to focus on a countryside stay, where choices range from simple accommodations with rustic charm to posh villas, or be in or around a town or village, and here, too, you’ll have many appealing options, from a simple bed and breakfasts to restored palaces.
You should spend at least a couple of days here
Lots of people just cruise into Chianti on a day trip from Florence or Siena, departing as night falls. And while any amount of time here is worth it, this beautiful corner of Tuscany is really ideal for longer stays.
To me, a big part of the pleasure of being here is settling in and leisurely savoring the rolling hills, making use of the hiking and biking trails, visiting vineyards, and taking meandering country drives.
The countryside accommodations that are abundant here often have lawns, gardens, pools, tennis courts, and other outdoor amenities that tempt guests not to do anything more than just relax, so this genuinely is a place to slow down and enjoy your surroundings.
Making a leisurely circuit of the towns and villages is very rewarding, too, and although they’re small, they’re very pretty and are perfect places to stop for a meal and go for a stroll.
Having a rental car is a must
Chianti is one of the few regions in Italy that is not served by train, and bus service is limited, with no through service along the relatively short route between Florence and Siena: Buses from Florence only go as far as south as Lucarelli, with stops in Greve, Panzano, and other towns along the way, and others go from Siena to Gaiole, Castellina. and Radda.
This means you can’t easily move between the major towns in the region by bus, from Greve to Radda, for example. Nor can you explore smaller villages, travel backroads, visit wineries, or reach most countryside accommodations without a car.
Chianti is really easy to reach
As rural and scenic as Chianti, the region is extremely accessible. Florence, with excellent high-speed train connections to the rest of Italy and an airport, is just to the north of the region and only half an hour from Greve.
Most major car-rental companies and many smaller ones have offices in central Florence and at the city’s Amerigo Vespucci airport. The region is also well connected to the A1 autostrada, Italy’s major north–south highway, with easy access onto the Chiantigiana, the scenic road through the Chianti countryside, from the outskirts of Florence and Siena. Via the A1, Greve, the largest town in Chianti, is 2 hours and 45 minutes north of Rome and a little more than 3 hours south of Milan.
You can stay nearby and still easily visit
It’s easy to visit Chianti from nearby towns. Florence and Siena are at the north and south of the region, respectively, and these are good bases for travelers who prefer being in a larger and livelier cities. Smaller Siena provides the easiest access onto the SR222/Chiantigiana road that bisects the region.
It’s also easy to explore the region from such outlying towns as Barberino Tavarnelle, at the far-western edge of Chianti, and Colle Val d’Elsa, a little farther west. These attractive towns also have easy access to the quick toll road, the Raccordo Autostradale, between Siena and Florence, so they are handy for touring beyond Chianti.
What to expect from a stay in Chianti
A square in Castellina in Chianti. Photo: Lorenzo Gaudenzi, CC BY-SA 4.0, via Wikimedia Commons
Lots of scenery
The largely rural area has not changed much over since 13th-century Florentine governors began laying claim to these desirable lands. The rolling countryside is covered in a mix of oak and chestnut forests, olive groves, and, of course, vineyards, and small towns and villages command many of the hilltops.
One of the most scenic roads in Italy, the Chiantigiana, climbs, dips, and curves across the hilly region for 60km (37 miles) between Florence, to the north and Siena, to the south. Great views are common currency in this part of the world, and the higher up you go, usually the better.
From Castagnoli, a hilltop hamlet surrounding a somber stone rocca, fortress, outside Castellina, the views take in not only the terraced vineyards that drop away beneath your feet but extend way west across forests and hills that roll toward the horizon.
Lamole is another scenic, view-filled spot, high up in the hills at the end of a cypress-lined road between Greve and Panzano.
Great wines
More than 300 Chianti wineries produce some of the most legendary vintages in the wine world, with the most notable wines denoted as Chianti Classico and bearing the trademark black rooster, Gallo Nero, on the label.
Many wineries are open to the public and offer tastings, usually with a choice of three to five wines, at varying prices, often accompanied by ham and cheese or other appetizers. You’ll probably also be able to take a look at the cellars and wine-production facilities, and almost all have shops and will ship internationally.
At some you’re welcome to walk through the vineyards, and a few offer meals in which food is paired with estate wines. Some wineries also accommodate guests (see below), usually in character-filled and often luxurious surroundings.
Character-filled places to stay
Accommodations in Chianti are much more than just places to lay your head for a night or two. They include farm estates, storybooks castles, remote abbeys, restored hamlets, and character-filled old palaces.
Many hotels are in notably beautiful settings, with extensive grounds overlooking quintessentially Tuscan backdrops of distant hilltop villages and rolling hills draped in vineyards and olive groves, and many have swimming pools and pretty gardens along with other outdoor amenities.
Even the more basic choices are usually loaded with charm. See below for some of the many options.
Very pretty and very small towns and villages
While the main appeal of the region lies in the beautiful landscapes, it’s also a pleasure to wander through the many towns and villages that appear every few miles along the region’s enticing back roads and are reliably quaint and picturesque.
Panzano’s medieval atmosphere and views across the countryside are topped by the presence of one of Italy’s most famous butchers, Dario Cecchini, who operates a shop and restaurant in the village.
Montespertoli is on a hillside above a patchwork of fields and vineyards with a medieval castle that was once the stronghold of the Machiavelli family.
Montefioralle is also magically atmospheric, surrounding a castle keep, with a double-circuit of medieval walls.
Volpaia and San Gusme are two charmingly medieval fortified villages still enclosed within their walls.
Among the larger towns are Castellina, built around a formidable fortress, or rocca, and with one street, the underground Via delle Volte, that tunnels beneath the city walls.
Radda is also surrounded by a circuit of thick city walls, and the somber, medieval Palazzo del Podesta is a reminder of the town’s onetime importance.
Greve, home to about 14,000 residents, is the largest town in Chianti and the unofficial capital; at the heart of town is a large square (actually, more of a triangle) surrounded by arcades that house cafes, wineshops, and enotecas.
Plenty of opportunities for hiking and biking
A network of well-marked strade bianche (gravel routes) laces the region and are ideal for hiking and biking, as are many secondary roads, which are mostly free of heavy traffic. Gaiole in Chianti, the start of the October L’Eroica gravel-path bike race, is the region’s biking center, and bike and e-bike rentals are available from shops in town.
Easy access to other parts of Tuscany
Tempting as it is to stay put in this beautiful part of the world, you’ll probably also want to do some exploring. Wherever you stay in Chianti, you’ll only be 30 minutes to an hour away from Siena or Florence, and both of these treasure troves of art and architecture top the must-see list for an Italian visit.
You can also get over to the Val d’Orcia, another region noted for its pretty hill towns, beautiful scenery, and wine, in an hour, or travel west in about the same amount of time to tower-topped San Gimignano then continue on to Volterra, with one of the world’s most important collections of Etruscan artifacts.
Arezzo, a lively and attractive city famous for its frescoes by Piero della Francesca, is about an hour to the southeast, and it’s an easy drive onward from there to Cortona, a proud and beautiful hill town with which you may already be familiar from the book and film Under the Tuscan Sun.
Where to stay
Beacause of its small size, no matter where you stay in Chianti you will be well-poised to explore the rest of the region. You can also rest assured that whether your lodgings are deep in the countryside or on the cobblestone lanes of an old village, they’re likely to be filled with character and an abundance of Tuscan charm.
Since where you stay geographically within the region is not actually all that important, I’ve decided to make my recommendations based on the type of accommodation rather than the town or area. As I’ve mentioned throughout this guide, Chianti is filled with beautifully restored historic properties and lovely accommodations with expansive grounds, and since I recommend exploring leisurely and actually spending time at your hotel/accommodation, I think the property you choose is really important.
And since there are a number of typical types of accommodation in Chianti, I’ve provided a quick overview below of each of those along with my favorite properties in each category.
Manor houses
Throughout the Middle Ages and Renaissance powerful families in Siena and Florence acquired vast tracts of land in what is now the Chianti region, building grand houses on their estates that produced prized wines, along with olives and other products.
Cosimo III de Medici officially put the region on the map when he stablished the boundaries of Chianti in 1716, making the land holdings even more valuable and desirable. Many of the estates have since been broken up, but the houses from which aristocrats once overlooked their holdings have been converted to character-filled hotels, usually surrounded by extensive grounds.
The aristocratic homeowners are often in residence to ensure their guests enjoy good food, comfortable accommodations, attentive service, and all the others pleasures of a privileged country-house stay.
Some of my favorites
Villa Le Barone (Panzano). A count and countess host guests at their charming manor house outside Panzano, where the old-world ambiance is enhanced with modern comforts and beautiful grounds. From 300 euros.
Badia a Coltibuono (Gaiole in Chianti). A stylishly converted abbey is set in a nature preserve high above Gaiole. From 180 euros.
Castello Vicchiomaggio (Greve in Chianti). A 700-year-old wine estate near Greve has hosted Leonardo da Vinci and other luminaries and now houses guests in a storybook, castle-like manor house and a beautifully restored priory. From 180 euros.
Castle hotels
Bucolic as the Chianti region is today, throughout the turbulent Middle Ages the ever-feuding lords of Siena and Florence, bitter rivals, fought over these lands that lie between the two cities. Powerful landholders defended their holdings against marauding armies from castles that still command strategic hilltops across the region.
Many of these walled and turreted compounds have been converted to hotels fitted out with spas and other modern luxuries.
Accommodations are often tucked into towers and turrets, great halls and other atmospheric space have been converted to dining rooms and lounges, and the extensive grounds, equipped with swimming pools and other amenities, often include winery operations.
Some of my favorites:
Castello del Nero (Barberino Tavarnelle). Frescoes and other medieval splendor abound at this 12th-castle and wine estate outside Barberino Tavarnelle, with modern comforts that include a lavish spa. From 700 euros.
Castello di Spaltenna (Gaiole in Chianti). A storybook castle set amid Sangiovese vineyards outside Gaiole pampers guests with amenities that include a restaurant in the Great Hall, a spa, and two swimming pools. From 400 euros.
Castello del Gabbiano (Mercatale in Val di Pesa). The romantic, turreted “Castle of the Seagull “ near Barberino Tavarnelle is surrounded by gardens, lawns, and vineyards, an idyllic setting for sipping the estate’s excellent wines. From 275 euros.
Castello la Leccia (Castellina in Chianti). Medieval ambiance combines with clean contemporary style in a castle and manor house on a working farm and winery outside Castellina. From 275 euros.
Castello di Querceto (Greve in Chianti). Apartments in a medieval castle and adjacent farmhouse outside Greve exude rustic Tuscan style and are on the grounds of a working wine estate. From 110 euros.
In-town accomodations
Towns in Chianti are small and usually have a few distinctive landmarks, such as medieval towns halls, grand piazzas, and in some, such as Radda and Castellina, fortresses and a ring of defensive walls. They are well supplied with shops, restaurants, and usually, outlets of the surrounding wineries, so an in-town stay puts these conveniences within walking distance.
Accommodations are often bed and breakfasts occupying apartments in older buildings or, in some cases, fine old palaces converted to full-service hotels.
Some of my favorites:
Hotel Palazzo Pacini (Col Val d’Elsa). A 17th-century palace in Col Val d’Elsa surrounds guests with comfort and historic ambiance. From 200 euros.
Palazzo Leopolodo (Radda in Chianti). A palace full of medieval salons and beamed guestrooms in the heart of Radda opens to a village square on one side and sweeping countryside on the other, providing in-town convenience along with rural beauty and amenities that include a spa and swimming pool. From 150 euros.
B and B L’Eroico (Gaiole). Basic but stylish accommodations in the center of Gaiole, the cycling center of Chianti, are a welcoming base for bikers and other travelers exploring the region. From 120 euros.
Grano e Lavanda (Greve). A pleasant and convivial bed and breakfast offers homey, attractive accommodations in a centuries-old palazzo just off the main square of Greve. From 110 euros.
Countryside settings
The appealing Chianti countryside is littered with rural lodgings that are less grand than manors and castles but no less appealing, These include poderi, farms, with accommodations in stone farmhouses and surrounding buildings, and in some cases entire rural farming hamlets where houses and outbuildings have been converted to posh quarters.
You’re likely to be surrounded by working farms and wineries, with products of the land at hand, and swimming pools and pleasant grounds are usually among the amenities.
Some of my favorites:
Borgo San Felice (Castelnuovo Berardenga). Guest rooms and cottages line the lanes and surround the piazza of a former farm settlement that’s still part of a working wine estate between Castellina and Siena. From 650 euros.
Borgo di Vescine (Radda in Chianti). A former farm-workers’ enclave of stone buildings connected by cobbled paths is now a stylish getaway outside Radda. From 330 euros.
Borgo del Cabreo (Greve). A stone house and restored farm buildings provide atmospheric accommodation on a hilltop wine estate high in the hills above Greve. From 300 euros.
La Locanda Country Hotel (Radda in Chianti). Character-filled accommodations in the converted stable yards on a hilltop outside Radda are as charming as they are comfortable and overlook miles of vineyards. From 175 euros.
Castello di Fonterutoli (Fonterutoli). Guest rooms in stone houses scattered around a rural hamlet outside Castellina are stylish and relaxing. From 170 euros.
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