Hilltop Towns of Tuscany: Siena & San Gimignano Tour

Get to the heart of two of Tuscany’s most iconic hilltop towns: Siena and San Gimignano with your own dedicated local guide.

The immersive Siena & San Gimignano Tour is your chance to step back in time and uncover the secrets of some of Tuscany’s most spectacular landmarks. A local expert will guide you through Siena, unveiling the city’s famous sights, including the Piazza del Campo and the Duomo. Stop for a 3-course lunch and wine tasting at a Tuscan wine estate before continuing on to San Gimignano, best known for its medieval towers. Within easy reach of your luxury villa in Tuscany, this enriching private experience offers the perfect blend of history, culture, and superb local cuisine.

Siena Private Tour with Vineyard Lunch & Wine Tasting

Your day will begin with a private transfer from your villa to Siena, where your expert guide will meet you to kick off a 3-hour walking tour of the historic centre. You’ll discover Siena’s most famous attractions, including the stunning Piazza del Campo, home to the world-renowned Palio horse race; Siena Duomo, one of Italy's most spectacular cathedrals; and the Baptistery. If you wish to visit any sites that require a ticket, you can decide this with your guide on the day for added flexibility. After your time in Siena, relax and indulge in a 3-course lunch paired with three local wines at a nearby Tuscan wine estate. Your lunch will be complemented by a tour of the estate’s vineyards and, depending on the time of year, a visit to the wine cellars.

Guided Tour of San Gimignano

In the afternoon, continue your adventure with a 2-hour guided tour of San Gimignano, with highlights including Piazza del Duomo, Piazza della Cisterna and the Church of Sant’Agostino. The “Medieval Manhattan” of Tuscany, this famous walled hilltown is known for its medieval towers and breathtaking views. As you wander through the narrow streets, your guide will point out hidden gems and offer fascinating insights into the town’s history.

The experience will begin with a 3-hour guided tour of Siena, followed by a vineyard tour, wine tasting, and lunch. In the afternoon, you will continue to San Gimignano for a 2-hour guided walking tour.

• Min. 2 persons — Max. 16 persons
• Available all year round
• Languages: English and Italian
• Child-friendly
• Advance booking of 1-2 months recommended
• Private transfers are highly recommended; transfer costs depend on the location of your villa and are not included in the displayed price.

Included in the price: Guided tour with earphones of Siena and San Gimignano. Tasting of 3 wines paired with a 3-course lunch at a Tuscan wine estate.