easy
6–8 hours
Suitable for most visitors with average fitness; moderate walking between sites required.
Travel through Tuscany’s historic heart with Under The Tuscan Sun Tours. From Siena’s cathedral to Chianti wines and San Gimignano’s towers, this private journey offers an authentic Italian escape.
Starting at € 390 | 8 Hours | Visit Siena and Monteriggioni
Embark on a unique private tour through Tuscany's historical gems, including Siena's stunning cathedral and the iconic Piazza del Campo. Explore the medieval fortress of Monteriggioni and indulge in a delightful wine tasting at a renowned Chianti producer. Conclude your adventure in San Gimignano, famous for its exquisite towers and world-class gelato.
Tour € 390–€ 1800
8 hours
Siena We will head towards the South of Tuscany to visit Siena. The historical enemy of Florence. Many battles were fought between the two cities. Only once Siena defeated Florence, 1260 4th september battle of Monteaperti. The rivalry is still strong as the sienese say that the best thing that happened to Florence was the 1966 flood that almost drowned the entire city.
Siena is the medieval and gothic jewel of Tuscany, not having been effected in a great manner by the Renaissance period.
Thanks to our official permits, we will drive through the pedestrian narrow, windy roads of the city to reach the beautiful recently renovated cathedral, right in the heart of town. Once we park the car, we will walk you through the main street and to one of the most breathtaking squares in Italy, Piazza del Campo. This is where the Palio Horse race is held; twice a year, July 2nd, August 16th. This is the reason the people of Siena are so proud Of their roots. Walk through the streets the days before the race and every citizen in the streets is putting up an act making it seem like they are part of an open-air theatre play Will then give you some free time until lunch time.
Monteriggioni Until the XI century Monteriggioni was a station of a standstill on the Francigena Road in Tuscany. Siena transformed Monteriggioni in the imposing Fortress to the protection of the boundary north in the wars against the enemy Florence. Inside Monteriggioni there were in XIV century beyond 150 families with about 600 inhabitants.
The wall was arisen since 1213 (see the headstone on the Romea Gate) until 1219 and then they strengthen in varied years (1260, 1279) until 1545. The wall up of Monteriggioni is long beyond 500 meters, tall twenty meters and surrounded from 14 towers to square base. The Fortress in the beyond two hundred years “of use” spent of the hand between Florence and Siena. Lunch. Early p.m. is our visit to one of the largest wine producers in Chianti to enjoy one of Italy’s Favourite sports: wine tasting.IMG-20160125-WA0018
San Gimignano Next is the town of San Gimignano, also known for its beautifully preserved medieval towers . 14 left out of 72 initially built in the 13th century.
We will walk you to the square of the well, the centre of the town for you to enjoy All the fine shops which also sell the local smooth, dry white wine called Vernaccia, and most of all the best ice cream in the world.
This private tour is popular and limited; advance booking ensures availability and personalized experience.
Expect cobblestone streets and uneven terrain in medieval towns, so sturdy walking shoes are recommended.
Bring a water bottle, especially during summer, as you’ll be walking between historic sites and vineyards.
Early visits to Siena and Monteriggioni avoid crowds and offer the best natural light for photos.
Monteriggioni’s fortress dates back to the early 13th century, built as a defensive bulwark during the conflicts between Siena and Florence.
The region promotes sustainable viticulture practices to preserve both soil health and traditional farming methods critical to Chianti’s character.
Necessary for navigating cobblestone streets and vineyard paths comfortably.
Weather can change rapidly; layering keeps you comfortable indoors and outdoors.
spring|fall|winter specific
Staying hydrated during the tour, especially during warmer months, is important.
summer|spring|fall specific
Capture the striking medieval architecture, vineyards, and Tuscan landscapes.