Tuscany Road Trip
Rolling hills, Renaissance art, Chianti wines, and the best pasta on Earth — la dolce vita in the Italian countryside.
Day-by-day itinerary
Day 1
Florence
Uffizi Gallery
Piazzale degli Uffizi
Ponte Vecchio walk
Ponte Vecchio
Lunch at Mercato Centrale
Via dell'Ariento
Duomo & Brunelleschi's Dome climb
Piazza del Duomo
Piazzale Michelangelo sunset
Piazzale Michelangelo
Bistecca fiorentina dinner
Trattoria Mario
Day 2
Florence
Accademia Gallery (David)
Via Ricasoli 58
San Lorenzo Market leather shopping
Piazza San Lorenzo
Lunch at All'Antico Vinaio
Via dei Neri 74
Boboli Gardens
Piazza de' Pitti
Oltrarno artisan workshops
Oltrarno
Day 3
Chianti
Drive through Chianti hills
SR222
Wine tasting at Castello di Brolio
Gaiole in Chianti
Lunch in Greve in Chianti
Piazza Matteotti
Radda in Chianti walk
Radda in Chianti
Drive to Siena
SR429
Dinner at Osteria Le Logge
Via del Porrione 33
Day 4
Siena
Piazza del Campo
Piazza del Campo
Siena Cathedral & Piccolomini Library
Piazza del Duomo
Lunch at Antica Osteria Da Divo
Via Franciosa 29
Drive to San Gimignano
RA3
San Gimignano towers & gelato
Piazza della Cisterna
Vernaccia wine at sunset
San Gimignano
Day 5
Val d'Orcia
Drive through Val d'Orcia
SP146
Pienza (pecorino cheese & views)
Pienza
Montepulciano & Vino Nobile tasting
Montepulciano
Farewell lunch at La Grotta
Montepulciano
Drive to Florence & depart
A1
Where to stay
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Things to do
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Travel essentials
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