Travel from Florence through rolling Chianti hills to Siena and medieval San Gimignano, finishing with a Tuscan dinner and wine tasting at a boutique winery. This full-afternoon (or upgraded full-day) excursion blends guided history, free time to wander, and regional flavors.
More ways to explore the area's outdoor wonders
A Mercedes minivan peels away from Florence at midafternoon and the city’s Renaissance facades give way to a patchwork of vineyards, olive groves and low stone walls. The road climbs through Chianti’s rounded hills; the air tightens with herbs and sun-warmed earth. By early evening the group is sitting at a long table in a low-slung winery while the valley’s last light slides across cypress silhouettes.
Difficulty
moderate
Duration
9–12 hours
Fitness Level
Moderate stamina for a long day with several short walks and some uphill cobbled streets; no special training required.
Wildlife
History
Siena and San Gimignano rose to prominence in the Middle Ages; Siena’s Contrade system still structures civic life and the surviving towers of San Gimignano marked medieval family power and trade wealth.
Conservation
Vineyards and hill towns face visitor pressure—support local producers, stick to town paths, and avoid trampling vineyard edges to help protect rural landscapes.
Reserve your spot on the Florence: Siena & San Gimignano with Dinner in a Boutique Winery today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Cobblestone Footing
Wear sturdy walking shoes—the towns are full of uneven cobbles and short steep sections, especially in San Gimignano.
Bring Water & Snacks
Carry a refillable bottle and small snacks for the walking portions; hydration stops are limited between towns.
Carry Small Cash
Some small shops and local vendors prefer cash for purchases and tastings in village markets.
Time for Photos
Schedule camera breaks during the drive through Chianti and at San Gimignano’s viewpoints—sunset light enhances vineyards and towers.
Sturdy walking shoes
Good grip and ankle support make cobbled streets and steep lanes more comfortable.
Refillable water bottle
Keeps you hydrated during walking and between scheduled stops.
Light layers and a windbreaker
Evening in the hills can be cool; layers adapt to sun and breeze.
fall
Compact daypack
Carries water, camera, and any purchases from markets or tastings.