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San Gimignano & Siena Tours

This tour lasts approximately 9 hours.

Enjoy a day of Medieval wonder in the heart of Tuscany,
beginning with a stop at historic Monteriggioni Castle.

Monteriggioni Castle: (1.5 hrs from Livorno)

Monteriggioni Castle, the most majestic and best-fortified castle of the Italian Middle Ages, remained an invincible fortress for more than three centuries. From the time of its construction in 1213 it resisted every siege, ensuring freedom to the Republic of Siena until 1554. Today it is a fun journey into the past, appreciated by children and adults alike.

Siena: (30 min from Monteriggioni)

Some people say Siena is the most beautiful city in Tuscany. The centre is dominated by Piazza del Campo, vast and shaped like a fan, which is the core of Siena's civic life. Here you will want to tarry a while, and if it rains, consider yourself lucky! You will get to see magic patterns of rainwater descending the cleverly laid paving stones.

Architecture buffs will appreciate Siena's great cathedral, begun in the 12th century in the Romanesque style but transformed in the 13th century into one of the finest examples of Italian Gothic. The church is dedicated to Santa Caterina and parts of her remains are enshrined within.

Language aficionados will know that Tuscany is the birthplace of the modern Italian language — and in Siena you will find the purest spoken Italian (no regional accent).

Siena also serves as a market for the surrounding agricultural area which produces cattle, cereal grains, olives, and, above all, its Chianti wines.

San Gimignano: (1 hour from Siena)

To reach San Gimignano we will pass through the most wonderful Tuscan countryside — classic rolling hills, vineyards and silvery green olive groves, a living picture postcard! The spectacle of the terrain is a tour unto itself.

San Gimignano, often referred to as “the Manhattan of Tuscany” or “the Manhattan of the Middle Ages” is best known for its watchtowers, which were a display of power and prosperity in Medieval times. Although only 14 of San Gimignano’s original 76 towers remain, it’s still more than enough to charm us and make for wonderful photos.

Take your time strolling the narrow cobbled streets and open piazzas, and be prepared to step back in time. Art lovers may wish to step into the church of Sant’Agostino where they will find a substantial selection of works by some of Italy’s major Renaissance painters. San Gimignano is also home to award-winning gelato, look for it in the main piazza.


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Please note

All tours are private and customizable.

All driver-guides speak English.

Private local guides are available for additional cost.

Food, beverages, entrance fees and gratuities (10%-15% common) are not included.

To enter churches you should have knees and shoulders covered. Sturdy walking shoes are advised; surfaces of streets and sidewalks can be uneven.