Plan Your Journey
Chianti
Itineraries
Three routes through the hills, villages,
and cellars of Chianti Classico.
The Road
The Strada Chiantigiana — the SR222 — is one of Italy's great drives. It winds 80 kilometres 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.
Enoteca Falorni, Greve
One of Tuscany's great wine shops, with an extraordinary cellar and a self-service tasting system letting you sample over 100 wines by the glass. An essential introduction to the appellation.
Enoteca Ristorante Gallo Nero, Greve
On the piazza, the Gallo Nero pairs a serious wine list — heavy on Chianti Classico producers — with a short menu of well-executed Tuscan classics. Order the ribollita and ask what's open by the glass.
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 famous salami to eat with bread and wine.
Villa Bordoni, Greve in Chianti
Return to Greve to check into Villa Bordoni — a Scottish-owned boutique villa with an outstanding wine list, a small pool, and rooms that look out over vine-terraced slopes.
Solociccia, Panzano
Drive back to Panzano for dinner at Dario Cecchini's communal meat feast — no menu, long tables, theatrical cuts of Florentine beef, lard candles, and Chianti flowing freely. Book well in advance.
Radda in Chianti → 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 corso.
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 biodynamic, and tastings in the old cellars beneath the village church are memorable.
Osteria Le Panzanelle, Lucarelli
A remote, rustic restaurant between Radda and Panzano — worth seeking out for its brilliant pappardelle with hare and deeply honest cooking. Booking essential.
Castellina in Chianti
Drive west to Castellina, an Etruscan hilltop town with the Rocca fortress and a charming 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
As the weekend itinerary — see above
Follow the Weekend Day 1 programme
Piazza Matteotti → Enoteca Falorni → Gallo Nero → Antica Macelleria Cecchini → Villa Bordoni check-in → Solociccia dinner.
Gaiole in Chianti
Abbeys, birthplaces of wine, and medieval towers
Badia a Coltibuono, Gaiole
Drive east to this 11th-century Benedictine abbey set deep in wooded hills above Gaiole. The estate produces outstanding organic 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, as codified by Baron Bettino Ricasoli in 1872. The castle commands extraordinary views across the valley. 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 cuisine alongside the full Barone Ricasoli range. The pici all'aglione is 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 Vigneto Bellavista Gran Selezione — are exceptional. Tastings by appointment.
Il Pievano at Castello di Spaltenna, Gaiole
Return to the 12th-century castle hotel for dinner at their Michelin-starred restaurant. If the budget allows, stay overnight at Spaltenna — it is among the finest hotels in the zone.
Radda → Volpaia → Castellina
As the Weekend Day 2 — the arc home
Follow the Weekend Day 2 programme
Radda in Chianti → Castello di Volpaia → Osteria Le Panzanelle lunch → Castellina in Chianti → depart.
Five days allow for a fuller immersion: the entire 3-day Chianti route, plus a great architectural winery, Siena, and San Gimignano on the way home.
Full 3-Day Chianti Route
Greve → Panzano → Gaiole → Radda → Castellina
Complete the 3-Day Itinerary above
Follow the full 3-day programme through Greve, Panzano, Gaiole, Radda, and Castellina before continuing south.
Antinori nel Chianti Classico → Siena
Architecture, art, and the greatest piazza in Italy
Antinori nel Chianti Classico, Bargino
Drive north of Greve to Bargino for one of the most architecturally remarkable wineries in the world — a vast subterranean building by Archea Associati (2012), invisible from above, burrowed into the hillside. The tasting room and restaurant are exceptional. Home to Tignanello and Solaia vineyards. Book ahead.
Siena
Drive south to Siena — the medieval rival to Florence and a UNESCO World Heritage city. Walk the extraordinary Piazza del Campo, climb the Torre del Mangia, and visit the Duomo. Stop at the Enoteca Italiana in the Medici Fortress for a final structured tasting of Tuscany's finest.
Siena — Osteria Le Logge or Trattoria Papei
Dine in Siena. Osteria Le Logge (elegant, great wine list) or Trattoria Papei (local institution on 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 northwest 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 — Italy's oldest DOC white wine — at Tenuta Il Colombaio di Santa Chiara or Montenidoli.
Colle di Val d'Elsa
Drive 15 minutes east to Colle di Val d'Elsa — less visited and more authentic than San Gimignano. Lunch at a simple trattoria in the medieval upper town (Colle Alta). The town is also famed for its crystal glass production.
Return north via the Chiantigiana
Rejoin the SR222 north toward Florence, stopping if time allows in Greve to pick up bottles from Enoteca Falorni for the journey home. The drive north through the vineyards in afternoon light is among the most beautiful in Italy.
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 90 minutes by road. Rome Fiumicino (FCO) is served by more intercontinental routes — allow 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 (1h45), 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 unsigned. Speed limits are strictly enforced. Many wineries and agriturismo have long gravel driveways — a high-clearance vehicle is useful. Designate a driver for winery visits, or use a taxi service from Greve or Radda for evening meals.
- ZTL (traffic restriction) zones apply in most village centres
- Petrol stations are sparse — fill up in Greve or Castellina
- Park outside village walls and walk in
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 tourist crowds are thinner than July–August. Harvest season (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 August 15 (Ferragosto). November–March is quiet, cool, and atmospheric — many estates and restaurants close for winter, but those that remain open offer a rare sense of solitude.