Tuscany
🇮🇹 Italy
UnknownSubregions
Trails
The Tuscany Grand Tour
This isn't just a wine trip—it's the wine trip you'll tell every dinner party about for the next 20 years. You'll descend a $110 million spiral staircase into the hillside at the #1 vineyard in the world. You'll stand where Brunello was invented in 1888, touching the same brick-vaulted cellar where Franco Biondi Santi hid wines from Nazi plunderers. You'll photograph Chapel Vitaleta at golden hour, creating that exact shot you've seen on 10 million Instagram posts. And you'll crawl through Renaissance-era cellars beneath Montepulciano, past Etruscan tombs, drinking wine aged in caves carved by hand 500 years ago. This is Tuscany the way it was meant to be experienced.
19 stopsClassic Tuscan Wine Road
The quintessential Italian wine journey through rolling hills, cypress-lined roads, and medieval hilltop towns. From Sangiovese heartland to underground cellars carved into tufa rock.
6 stopsEtruria Heritage
Before Rome conquered Tuscany, the Etruscans were Italy's master winemakers. Rome absorbed and spread Etruscan wine knowledge across the empire. This adventure traces Tuscan wine DNA back 3,000 years—from Etruscan tombs to Super Tuscans.
10 stopsVenues (59)
Chianti Classico Consortium
winery
Osteria Acquacheta
restaurant
Ornellaia, Osteria San Guido
winery
Castello di Ama
winery
Chianti Classico - Antinori
winery · Bargino
Castellina in Chianti & Etruscan Tombs
wine_region · Castellina in Chianti
Montepulciano - Vino Nobile
wine_region · Montepulciano
Public piazza
landmark
Masseto
winery
Festa dell'Uva Impruneta
festival_grounds
San Gimignano: Medieval Manhattan & Vernaccia
wine_region
Antinori, Castello di Ama
winery
Consorzio del Vino Brunello
winery
Ercolani, Contucci, De Ricci
winery
Vin Santo & Biscotti Masterclass
school
Truffle Hunt & Wine Pairing in Crete Senesi
wine_region
Antinori
winery
Morellino di Scansano Maremma Safari
wine_region
Castello di Brolio
winery · Gaiole in Chianti
Biondi Santi
winery
Chapel Vitaleta Sunrise Photography
wine_region
Enoteca Pitti Gola e Cantina
wine_bar
Dario Cecchini
restaurant
Poggio Antico
winery
Enoteca la Fortezza di Montalcino
wine_bar
Enoteca Tognoni
wine_bar
Cantine Contucci
winery
Florence Archaeological Museum
winery · Florence
Volterra - Etruscan Capital
winery · Volterra
Bolgheri - Super Tuscan Coast
wine_bar · Bolgheri
Populonia & Gulf of Baratti
winery · Populonia
Podere Belvedere Scenic Drive
wine_region
Val d'Orcia to Bolgheri Transfer
wine_region
Tenuta San Guido (Sassicaia)
winery
Ornellaia
winery
Biondi-Santi
winery
Case Basse di Soldera
winery
Poggio di Sotto
winery
Greve in Chianti Evening
restaurant
Pienza: Pecorino & Wine Capital
winery
Viale dei Cipressi: The Cypress Road
wine_region
Tenuta San Guido
winery · Bolgheri
Isole e Olena
winery · Barberino
Enoteca Italiana
wine_shop · Siena
Ornellaia
winery · Bolgheri
Antinori nel Chianti Classico
winery · San Casciano in Val di Pesa
Biondi-Santi
winery · Montalcino
Fontodi
winery · Panzano in Chianti
Castello di Ama
winery · Gaiole in Chianti
Casanova di Neri
winery · Montalcino
Montevertine
winery · Radda in Chianti
Castello Banfi
winery · Montalcino
Frescobaldi (Castelgiocondo)
winery · Montalcino
Le Macchiole
winery · Bolgheri
Montalcino - Brunello Kingdom
wine_bar · Montalcino
Cortona & Eastern Tuscany
winery · Cortona
Morellino di Scansano
wine_bar · Scansano
Casanova di Neri
winery
Il Poggione
winery · Montalcino