Itineraries for Your Trip to San Gimignano
3 Days in San Gimignano for First Timers
With soaring towers piercing the skies above medieval rooftops, San Gimignano is one of the most impressive towns in Tuscany. More than just the quintessential Tuscan hill town, however, this blockbuster destination is the ideal base for exploring the pastoral landscapes and gem-like towns of Chianti, Val d’Orcia, and Crete Senesi.
It was its guidebook fame that drew me to San Gimignano on my first “check-list” tour through Tuscany, but over subsequent, slower-paced trips, I have been able to penetrate the tourist crowds and discover a quieter, more authentic side of this hilltop treasure. Here’s how to take in San Gimignano and the surrounding vineyards, olive groves, and villages for the first time in three days.
The Tuscan heat can be relentless in the summer, so arm yourself with sunblock, a hat, and water.
If you only have time for one thing, make it Torre Grossa for one of Tuscany's most stunning views.
Savor the time-capsule atmosphere of San Gimignano and explore the town’s delights inside and outside the medieval city walls. Explore the historic center, a UNESCO World Heritage Site. See its 14 soaring towers, the Collegiate Church of Santa Maria Assunta, Piazza Duomo and Piazza della Cisterna, and the remains of the town’s 16th-century fortress.
In the afternoon, set off through the Chianti countryside to visit the picture-perfect hill towns of Radda, Greve, and Castellina in Chianti. Hike, bike, or take a scenic drive between each; wine enthusiasts can relax at a local winery for a tour and tasting, too.
Head south to another of Tuscany’s UNESCO treasures: Siena. Thick with architectural masterpieces and views across the undulating Crete Senesi and Val d’Orcia, this historic town can get overrun with crowds by midday, so arrive early to savor the exquisite Gothic cathedral—home to works by Donatello, Michelangelo, and Bernini—in relative peace.
After lunch, take a deep dive into Siena’s medieval center. Stroll through the Piazza del Campo, Palazzo Pubblico, Torre del Mangia, and Basilica di San Domenico with a guide to learn about the Palio festival. This historic Italian celebration centers around a horse race between the town’s 17 contrade (districts).
Less famous than Siena, the Tuscan hill town of Volterra is no less storied. Its history stretches back to the Etruscans eight centuries before Christ. Today, it's home to archaeological ruins and a museum. Explore its historic center, with the 13th-century Palazzo dei Priori city hall, cathedral with famous artworks, and Roman theater. A highlight is Via Porta all’Arco, lined with artisan workshops turning out paper, leather, bronze, and gold.
Alternatively, head to the hills of the Val d’Orcia. The Renaissance town of Pienza is bookended by the wine countries of Montepulciano and Montalcino, producing some of Italy’s finest red wines.
