Day 1: Florence to Chianti — The Black Rooster Territory
Pickup from your Florence hotel by private driver-guide. Drive south into the Chianti Classico hills. First stop: an organic family-run estate where the owner personally guides you through vineyards planted with Sangiovese, Canaiolo, and Colorino grapes. Walk the barrel room where Chianti Classico ages in large Slavonian oak botti and smaller French barriques. Tasting: Chianti Classico, Riserva, and Gran Selezione with local pecorino cheeses, prosciutto Toscano, and estate olive oil. Lunch at the winery paired with their wines. Afternoon: a second estate featuring Chianti Classico and IGT Super Tuscans. Continue through the medieval hill town of Colle di Val d’Elsa. Overnight in Chianti countryside.
Day 2: Montalcino & Val d’Orcia — The Kingdom of Brunello
Morning: drive through the UNESCO Val d’Orcia to Montalcino. This hilltop fortress town is synonymous with Brunello di Montalcino — the first Italian wine to receive DOCG status and still arguably Italy’s greatest red. Visit two prestigious estates: first, a historic producer whose cellars date to the 16th century, for a vertical tasting of Brunello across multiple vintages — the differences between a young and an aged Brunello are a revelation. Second, a small boutique estate producing fewer than 10,000 bottles annually where the winemaker personally leads the tasting. Lunch at a Michelin-recommended restaurant in Montalcino with panoramic Val d’Orcia views. Afternoon: drive the iconic cypress-lined roads of the Val d’Orcia, stopping at photo viewpoints that have appeared in countless films and advertisements. Overnight Montalcino area.
Day 3: Bolgheri & Volterra — Super Tuscans and Etruscan Mysteries
The morning delivers Tuscany’s most famous road: the Viale dei Cipressi at Bolgheri — a perfectly straight 5-kilometer avenue of 2,540 cypress trees leading to the medieval village. Bolgheri is the birthplace of the ‘Super Tuscans’ that revolutionized Italian wine in the 1970s — Sassicaia, Ornellaia, Masseto. Visit a Bolgheri estate for a tasting of these iconic wines and learn the fascinating story of how renegade winemakers defied Italian wine laws and created some of the world’s most coveted bottles. Afternoon: Volterra — a dramatic walled city perched on a high plateau with Etruscan roots stretching back 3,000 years. Walk the Porta all’Arco (an Etruscan gate from the 4th century BC), the Roman Theatre, and the alabaster workshops for which Volterra has been famous since Etruscan times. Overnight Volterra area.
Day 4: San Gimignano, Vernaccia & Pisa
Morning: San Gimignano, the ‘Medieval Manhattan.’ Climb the Torre Grossa for views of the 14 remaining medieval towers. Visit a Vernaccia di San Gimignano winery — Tuscany’s only DOCG white wine, made from the Vernaccia grape cultivated here since the 13th century and praised by Dante. Afternoon: the perfect conclusion — Pisa’s Piazza dei Miracoli (Square of Miracles): the Leaning Tower (climb if desired), the stunning Romanesque Cathedral, the Baptistery (with its famous echo), and the monumental Camposanto cemetery. Return transfer to Florence. Arrivederci Toscana.
