Grand tour of Tuscany on a day trip from Florence to Pisa, Siena and San Gimignano

Siena is one of the most perfectly preserved medieval cities in Europe and it is a completely different aesthetic from Florence. Where Florence is Renaissance and grand, Siena is Gothic and intimate, built on three hills with a streetscape that looks almost unchanged from the 13th century. The Piazza del Campo, the scallop-shaped main square, is considered one of the finest public spaces in the world and was the site of the Palio horse race since at least 1310. A day trip gives you enough time to experience the square, the Duomo, and the surrounding streets. With a guide who contextualises the Florentine-Sienese rivalry, the city takes on a completely new dimension.

San Gimignano is famous above all for its 14 surviving medieval towers, originally there were 72, which give the town its distinctive skyline and earned it the nickname "Manhattan of the Middle Ages." These towers were status symbols built by rival noble families between the 12th and 13th centuries: the taller your tower, the more powerful your family. The town is a UNESCO World Heritage Site. It is also famous for Vernaccia di San Gimignano, the first Italian wine to receive DOC status in 1966, and for what is widely considered the best gelato in Italy, made by the Dondoli family at Gelateria Dondoli.

Chianti is a red wine from the hills between Florence and Siena, produced primarily from the Sangiovese grape. Chianti Classico, from the original historic zone between Greve in Chianti, Panzano, Radda, and Gaiole, is considered the finest expression and carries the black rooster (Gallo Nero) seal on the bottle. What makes Chianti special is the combination of the Sangiovese grape's natural acidity and tannins with the Tuscan terroir: the clay-limestone soils, the altitude, and the temperature variation between day and night. At its best, Chianti Classico Riserva is one of Italy's great red wines, structured, age-worthy, and distinctly Tuscan in character.

The Piazza del Campo is Siena's main public square  and one of the most beautiful medieval squares in the world. It is distinctive for its shell-like shape (divided into nine sections representing the Council of Nine that governed medieval Siena), its brick paving that slopes gently toward the center, and the Palazzo Pubblico and Torre del Mangia that anchor one side. Twice a year (July 2 and August 16) it becomes the track for the Palio di Siena — the famous bareback horse race run around its perimeter that is among the most dramatic annual events in Europe.

Siena is approximately 70 kilometres from Florence, about 1 hour 15 minutes by direct coach (the fastest option, from Santa Maria Novella station) or 1 hour 30 minutes to 2 hours by train (which requires a change at Empoli or Chiusi). By car it takes about 75 minutes. Siena is very much worth a day trip but is best visited with a guide, the city's medieval street layout is confusing without orientation, and the art and history of the Duomo and Palazzo Pubblico require context to fully appreciate. Our day trip combines Siena, San Gimignano, and the Chianti region in one perfectly structured day.

Cancellations are free up to 24 hours before the tour departure. For cancellations made within 24 hours of the tour start time, as well as in case of no-shows, the full amount will be charged.