Plan Your Journey
Chianti
Itineraries
Routes through the hills, villages, and cellars of Chianti Classico.
The Strada Chiantigiana — the SR222 — is one of Italy’s great drives. It winds between Florence and Siena through cypress alleys, hilltop villages, and an unbroken corridor of vine. These itineraries follow that road and the lanes that branch from it, taking you into the cellars, kitchens, and landscapes that define the zone.
Two days is enough to taste the heart of Chianti Classico. Base yourself in Greve or Panzano and let the Chiantigiana do the rest.
Greve in Chianti → Panzano
Arrive, taste, eat, sleep
Piazza Matteotti, Greve in Chianti
Arrive in Greve and walk the arcaded triangular piazza — the social heart of the Chianti zone. Pick up provisions at the morning market if visiting on Saturday.
Le Cantine di Greve in Chianti
One of Tuscany’s great wine shops, formerly Enoteca Falorni, with an extraordinary cellar and a self-service tasting system that lets you sample a large selection of wines by the glass. An essential introduction to the appellation.
Antica Macelleria Cecchini, Panzano
Drive the Chiantigiana south to Panzano. Stop at Dario Cecchini’s legendary butcher shop — part theatre, part shrine to Florentine beef culture. Buy lardo or a chunk of his salami to take home.
Solociccia, Panzano
Then sit down at Dario’s communal table at Solociccia, Via XX Luglio 11: no menu, long shared tables, a procession of Florentine beef preparations and Chianti flowing freely — €50 per person, wine included. Book well in advance.
Villa Bordoni, Greve in Chianti
Return towards Greve to check into Villa Bordoni — an eleven-room boutique villa in the hills above the town, with an outstanding wine list, a small pool and rooms that look out over vine-terraced slopes.
Enoteca Ristorante Gallo Nero, Greve
Just off the piazza, the Gallo Nero pairs a serious wine list — heavy on Chianti Classico producers — with fresh pasta made in-house and well-executed Tuscan classics. Order the ribollita and ask what’s open by the glass. Or stay in and dine at Il Guardingo, Villa Bordoni’s own restaurant.
Radda in Chianti → Volpaia → Castellina
Medieval walls, high cellars, the road home
Radda in Chianti
Drive east to Radda, the zone’s historic capital. Walk the medieval walls that encircle the village, stop at the 15th-century Palazzo del Podestà, and have a coffee at one of the bars on the main street.
Castello di Volpaia, Volpaia
A 15-minute drive north brings you to the tiny medieval hamlet of Volpaia, which is also a working winery. The estate is certified organic, and tastings in the old cellars within the village are memorable. Bar Ucci, on the square, is good for a glass on the terrace.
Osteria Le Panzanelle, Lucarelli
A remote, rustic restaurant between Radda and Panzano, with a MICHELIN Bib Gourmand — worth seeking out for its brilliant pappardelle with hare and deeply honest cooking. Booking essential.
Castellina in Chianti
Drive west to Castellina, a hilltop town of Etruscan origin with its Rocca fortress and a main street lined with wine shops. Visit Enoteca Le Volte for last-minute wine purchases before departure.
Three days allow you to add Gaiole — the most historically profound corner of the Chianti Classico zone — to the weekend route. This is the ideal introduction.
Greve in Chianti → Panzano
Arrive, taste, eat, sleep
Piazza Matteotti, Greve in Chianti
Arrive in Greve and walk the arcaded triangular piazza — the social heart of the Chianti zone. Pick up provisions at the morning market if visiting on Saturday.
Le Cantine di Greve in Chianti
One of Tuscany’s great wine shops, formerly Enoteca Falorni, with an extraordinary cellar and a self-service tasting system that lets you sample a large selection of wines by the glass. An essential introduction to the appellation.
Antica Macelleria Cecchini, Panzano
Drive the Chiantigiana south to Panzano. Stop at Dario Cecchini’s legendary butcher shop — part theatre, part shrine to Florentine beef culture. Buy lardo or a chunk of his salami to take home.
Solociccia, Panzano
Then sit down at Dario’s communal table at Solociccia, Via XX Luglio 11: no menu, long shared tables, a procession of Florentine beef preparations and Chianti flowing freely — €50 per person, wine included. Book well in advance.
Villa Bordoni, Greve in Chianti
Return towards Greve to check into Villa Bordoni — an eleven-room boutique villa in the hills above the town, with an outstanding wine list, a small pool and rooms that look out over vine-terraced slopes.
Enoteca Ristorante Gallo Nero, Greve
Just off the piazza, the Gallo Nero pairs a serious wine list — heavy on Chianti Classico producers — with fresh pasta made in-house and well-executed Tuscan classics. Order the ribollita and ask what’s open by the glass. Or stay in and dine at Il Guardingo, Villa Bordoni’s own restaurant.
Gaiole in Chianti
Abbeys, the birthplace of modern Chianti, and medieval towers
Badia a Coltibuono, Gaiole
Drive east to this 11th-century abbey set deep in wooded hills above Gaiole. The estate has farmed organically since the mid-1980s and makes outstanding Chianti Classico. Tour the Romanesque church, explore the gardens, and visit the enoteca.
Castello di Brolio, Gaiole
The most historically significant estate in all of Chianti — the birthplace of the modern Chianti formula, set down by Baron Bettino Ricasoli in 1872. The castle commands extraordinary views across the valley, and the Barone Ricasoli Gran Selezione is among the finest wines in the zone.
Osteria di Brolio, Gaiole
Eat within the Brolio estate — a refined but unshowy restaurant serving traditional Chianti cooking alongside the full Barone Ricasoli range. The pici all’aglione are essential.
Castello di Ama, Gaiole
One of Chianti Classico’s great art-focused estates, with permanent site-specific installations by Louise Bourgeois, Anish Kapoor, Daniel Buren and others. The wines — particularly L’Apparita Merlot and the Vigneto Bellavista Gran Selezione — are exceptional. Tastings by appointment.
Il Pievano at Castello di Spaltenna, Gaiole
Return to the 12th-century castle hotel above Gaiole for dinner at its MICHELIN-starred restaurant, where chef Antonio Iacoviello cooks. If the budget allows, stay the night at Spaltenna — it is among the finest hotels in the zone.
Radda in Chianti → Volpaia → Castellina
Medieval walls, high cellars, the road home
Radda in Chianti
Drive east to Radda, the zone’s historic capital. Walk the medieval walls that encircle the village, stop at the 15th-century Palazzo del Podestà, and have a coffee at one of the bars on the main street.
Castello di Volpaia, Volpaia
A 15-minute drive north brings you to the tiny medieval hamlet of Volpaia, which is also a working winery. The estate is certified organic, and tastings in the old cellars within the village are memorable. Bar Ucci, on the square, is good for a glass on the terrace.
Osteria Le Panzanelle, Lucarelli
A remote, rustic restaurant between Radda and Panzano, with a MICHELIN Bib Gourmand — worth seeking out for its brilliant pappardelle with hare and deeply honest cooking. Booking essential.
Castellina in Chianti
Drive west to Castellina, a hilltop town of Etruscan origin with its Rocca fortress and a main street lined with wine shops. Visit Enoteca Le Volte for last-minute wine purchases before departure.
Five days allow a fuller immersion: the entire 3-day Chianti route, plus a great architectural winery, Siena, and San Gimignano on the way home.
Greve in Chianti → Panzano
Arrive, taste, eat, sleep
Piazza Matteotti, Greve in Chianti
Arrive in Greve and walk the arcaded triangular piazza — the social heart of the Chianti zone. Pick up provisions at the morning market if visiting on Saturday.
Le Cantine di Greve in Chianti
One of Tuscany’s great wine shops, formerly Enoteca Falorni, with an extraordinary cellar and a self-service tasting system that lets you sample a large selection of wines by the glass. An essential introduction to the appellation.
Antica Macelleria Cecchini, Panzano
Drive the Chiantigiana south to Panzano. Stop at Dario Cecchini’s legendary butcher shop — part theatre, part shrine to Florentine beef culture. Buy lardo or a chunk of his salami to take home.
Solociccia, Panzano
Then sit down at Dario’s communal table at Solociccia, Via XX Luglio 11: no menu, long shared tables, a procession of Florentine beef preparations and Chianti flowing freely — €50 per person, wine included. Book well in advance.
Villa Bordoni, Greve in Chianti
Return towards Greve to check into Villa Bordoni — an eleven-room boutique villa in the hills above the town, with an outstanding wine list, a small pool and rooms that look out over vine-terraced slopes.
Enoteca Ristorante Gallo Nero, Greve
Just off the piazza, the Gallo Nero pairs a serious wine list — heavy on Chianti Classico producers — with fresh pasta made in-house and well-executed Tuscan classics. Order the ribollita and ask what’s open by the glass. Or stay in and dine at Il Guardingo, Villa Bordoni’s own restaurant.
Gaiole in Chianti
Abbeys, the birthplace of modern Chianti, and medieval towers
Badia a Coltibuono, Gaiole
Drive east to this 11th-century abbey set deep in wooded hills above Gaiole. The estate has farmed organically since the mid-1980s and makes outstanding Chianti Classico. Tour the Romanesque church, explore the gardens, and visit the enoteca.
Castello di Brolio, Gaiole
The most historically significant estate in all of Chianti — the birthplace of the modern Chianti formula, set down by Baron Bettino Ricasoli in 1872. The castle commands extraordinary views across the valley, and the Barone Ricasoli Gran Selezione is among the finest wines in the zone.
Osteria di Brolio, Gaiole
Eat within the Brolio estate — a refined but unshowy restaurant serving traditional Chianti cooking alongside the full Barone Ricasoli range. The pici all’aglione are essential.
Castello di Ama, Gaiole
One of Chianti Classico’s great art-focused estates, with permanent site-specific installations by Louise Bourgeois, Anish Kapoor, Daniel Buren and others. The wines — particularly L’Apparita Merlot and the Vigneto Bellavista Gran Selezione — are exceptional. Tastings by appointment.
Il Pievano at Castello di Spaltenna, Gaiole
Return to the 12th-century castle hotel above Gaiole for dinner at its MICHELIN-starred restaurant, where chef Antonio Iacoviello cooks. If the budget allows, stay the night at Spaltenna — it is among the finest hotels in the zone.
Radda in Chianti → Volpaia → Castellina
Medieval walls, high cellars, Etruscan Castellina
Radda in Chianti
Drive east to Radda, the zone’s historic capital. Walk the medieval walls that encircle the village, stop at the 15th-century Palazzo del Podestà, and have a coffee at one of the bars on the main street.
Castello di Volpaia, Volpaia
A 15-minute drive north brings you to the tiny medieval hamlet of Volpaia, which is also a working winery. The estate is certified organic, and tastings in the old cellars within the village are memorable. Bar Ucci, on the square, is good for a glass on the terrace.
Osteria Le Panzanelle, Lucarelli
A remote, rustic restaurant between Radda and Panzano, with a MICHELIN Bib Gourmand — worth seeking out for its brilliant pappardelle with hare and deeply honest cooking. Booking essential.
Castellina in Chianti
Drive west to Castellina, a hilltop town of Etruscan origin with its Rocca fortress and a main street lined with wine shops. Enoteca Le Volte is the place to stock up. Stay the night in Castellina or return to your base.
Antinori nel Chianti Classico → Siena
Architecture, art, and the greatest piazza in Italy
Antinori nel Chianti Classico, Bargino
Drive north-west to Bargino, in the comune of San Casciano in Val di Pesa, for one of the most architecturally remarkable wineries in the world — a vast cellar by Archea Associati (2012), burrowed into the hillside and almost invisible from above. The tasting room and restaurant are exceptional. Book ahead.
Siena
Drive south to Siena — Florence’s medieval rival and a UNESCO World Heritage city. Walk the extraordinary Piazza del Campo, climb the Torre del Mangia, and visit the Duomo.
Fèlsina, Castelnuovo Berardenga
If time allows, detour east of Siena to Castelnuovo Berardenga, the southernmost corner of Chianti Classico, for a tasting at the Fèlsina estate. Book ahead.
Siena — Osteria Le Logge or Antica Trattoria Papei
Dine in Siena. Osteria Le Logge (elegant, with a great wine list) or Antica Trattoria Papei (a local institution on Piazza del Mercato, just behind the Campo — unfussy and excellent) are both reliable choices. Stay overnight in Siena.
San Gimignano → Colle di Val d’Elsa → Home
Towers, Vernaccia, and a long road north
San Gimignano
Drive north-west from Siena to the famous skyline of San Gimignano — 14 medieval towers rising from a hill above the Val d’Elsa. Arrive early, before the coaches. Taste Vernaccia di San Gimignano DOCG — the first Italian wine to be granted DOC status — at Tenuta Il Colombaio di Santa Chiara or Montenidoli.
Colle di Val d’Elsa
Drive south-east to Colle di Val d’Elsa — less visited than San Gimignano and famed for its crystal glass. For a grand lunch, book well ahead at Arnolfo (2 MICHELIN stars); otherwise eat at a simple trattoria in the medieval upper town, Colle Alta.
La Chiantigiana
Rejoin the SR222 north towards Florence, stopping in Greve if time allows to pick up bottles at Le Cantine di Greve in Chianti for the journey home. The drive north through the vineyards in afternoon light is among the most beautiful in Italy.
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Before You Go
Practical Information
Getting There
Florence Airport (FLR) is the closest gateway, with connections from most European hubs. Pisa Galileo Galilei (PSA) is about 90 minutes by road. Rome Fiumicino (FCO) is served by more intercontinental routes — allow around 2.5 hours by fast train to Florence, then hire a car.
Florence Santa Maria Novella is the main hub. High-speed Frecciarossa trains connect Milan (about 1h55), Rome (1h30) and Venice (2h15). From Florence, hire a car — there is no practical rail access into the Chianti hills.
Getting Around
A car is essential. The SR222 Strada Chiantigiana is the spine of any Chianti itinerary. Many of the best estates, villages and restaurants are only reachable by car — often via unpaved strade bianche. Hire in Florence or at the airport. GPS navigation is strongly recommended.
Roads are narrow, winding and often poorly signed, and speed limits are strictly enforced. Many wineries and agriturismi have long gravel driveways — a car with good ground clearance helps. Designate a driver for winery visits, or use a taxi from Greve or Radda for evening meals. ZTL (restricted traffic) zones apply in most village centres: park outside the walls and walk in. Petrol stations are sparse — fill up in Greve or Castellina.
Best Time to Visit
May–June and September–October are the ideal months. The hills are green or golden, temperatures are mild (18–26 °C), and the crowds are thinner than in July and August. Harvest season, from late September to mid-October, is particularly magical.
July–August is hot (32–38 °C) and busy — book everything well in advance. Many restaurants close around Ferragosto (15 August). November–March is quiet, cool and atmospheric — many estates and restaurants close for the winter, but those that stay open offer a rare sense of solitude.