After pickup from your central Florence hotel, travel by private sedan or minivan (depending on numbers in your group) to San Gimignano, nestled deep in Tuscany.
Pass through the charming Chianti region, and as you near San Gimignano, note the vineyards that produce Vernaccia white wine, considered one of Italy’s best varieties.
Then, admire your first sight of San Gimignano’s hilltop skyline: a cluster of 14 medieval towers ringed by 13th-century walls. Originally an Etruscan settlement, the town once boasted 72 of these tower-houses constructed by its elite families to demonstrate their riches.
On arrival, hop out of your vehicle and enjoy ample free to explore and relax on your own. Delve into the old center, admiring the cobbled streets of Romanesque and Gothic architecture, and taking in the town’s heart — the beautiful triangular square, Piazza della Cisterna.
Head inside San Gimignano Cathedral (Il Duomo) to view its vivid 14th-century frescoes, and visit the Palazzo del Podestà, the original town hall building. Then, for more artistic treasures, continue to the 13th-century Church of Sant'Agostino, famous for its fresco cycle by Benozzo Gozzoli.
If you wish, crown your visit with a climb up one of the towers like the Torre Grossa or Torre della Rognosa, to experience the bird's-eye views over the town and countryside.
Relax over a coffee or gelato (ice cream) at one of the many ice cream parlors that sprinkle the town. Or if you’re a wine lover, call at the Vernaccia Museum (own expense), to chart the story of the local wine.
Lastly, maybe wander along the main street, Via San Giovanni, to peruse the shops selling everything from ceramics and leather bags to culinary goodies.
When it’s time, return to Florence, where your trip concludes with a hotel drop-off.