San Gimignano and Siena Private Tour

Quaint towns where time seems to have come to a halt. Mesmerizing piazzas and ancient traditions. Vineyards and rolling hills. A private tour from Florence to Siena and San Gimignano is one of the best ways to experience the authentic heart of Tuscany.
All in full comfort, of course, with your dedicated driver and private guide. Spend a memorable day exploring two small Tuscan gems filled with art and centuries of history.

DISCOVER MEDIEVAL SIENA

Meet your private dedicated English-speaking driver and travel from Florence to Siena, one of the most enchanting medieval cities in Italy.
Siena, founded by the Romans, boasts an exciting history and striking architecture. Its local traditions are equally fascinating, especially the famous Palio di Siena held in the magnificent Piazza del Campo.
Here, twice a year, horses representing the city’s historic contrade compete in a dramatic race, a tradition which dates back to the Middle Ages and still calls to all Senesi.
Hear your guide recount fascinating legends as you wander down medieval streets and visit the magnificent Duomo, Siena’s awe-inspiring Cathedral.

TRAVEL THROUGH THE TUSCAN COUNTRYSIDE

Depart Siena and surrender to the journey. The road between Siena and San Gimignano is one of Tuscany's most quietly breathtaking,a landscape that unfolds slowly, as if it knows it has your full attention. Silvery olive groves shimmer in the afternoon light, gently rolling hills carry golden farmhouses that look as though they've grown naturally from the earth, and quaint parish churches appear around bends in the road with a kind of effortless grace. Cypress trees line the crests of the hills like sentinels, and vineyards stretch in every direction — the same vines that have been here for centuries, producing the wines you'll taste later in the day. This is the Tuscany of painters and poets, and traveling through it by private car, with no schedule to chase and no crowds to navigate, is a privilege that very few visitors get to experience. Take it in slowly. It deserves it.

EXPLORE SAN GIMIGNANO

After Siena, it will be time to visit another gem of Tuscany, delightful San Gimignano, for a leisurely stroll and a browse in the charming shops.
Renowned as the “City of Beautiful Towers,” San Gimignano is one of Tuscany’s most iconic and best-preserved medieval towns.
Roam the quaint cobblestone streets, see the graceful tall towers and browse the pretty shops lined with bottles of Vernaccia di San Gimignano, premium saffron, dainty hand-woven linens and precious hand-made Santa Fina pottery.

ENJOY DINNER AT A BOUTIQUE WINERY

After visiting San Gimignano, set off once more through the hills.
Admire the vineyards and, as the light starts changing and crimson-hued clouds come forth, stop at a charming boutique winery for a brief visit and memorable dinner.
Crown your day in typical Tuscan style: a delicious dinner paired with the estate’s wines.
Our signature Siena and San Gimignano tour from Florence is an unforgettable Tuscan lifestyle experience.