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Discover Tuscany’s iconic hill towns Siena and San Gimignano on this private day trip from Florence, including a scenic drive, wine tasting, and a Tuscan lunch.
Exploring the scenic beauty and historic charm of Tuscany becomes effortless with the Private Best of Tuscany Hill Towns Tour from Florence. Priced at $662.98 per person, this 9-hour journey offers an intimate experience with limited groups and personalized attention. The tour features visits to Siena and San Gimignano, two of the region’s most captivating towns, along with a wine tasting and a traditional Tuscan lunch. An expert English-speaking driver-guide leads the way in a luxurious private Mercedes minivan, ensuring comfort and insightful commentary throughout the day.
This tour is ideal for those seeking a customized, hassle-free exploration of Tuscany’s picturesque hill towns. While the price might seem high, the all-inclusive nature—covering transport, visits, tastings, and lunch—delivers strong value. It is especially suited for travelers who appreciate small groups, personalized service, and media-rich scenery paired with culture.


The tour begins at 8 am in Piazza della Repubblica in Florence. Travelers are greeted by their local expert driver-escort, who provides a comfortable and stylish A/C Mercedes minivan for the day. The private nature of this tour guarantees an intimate environment, free from the crowds typical of larger group trips. The scenic drive through the Tuscan countryside sets the tone for a day filled with history, views, and culture.
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The first major stop is Siena, famous for its Palio di Siena, a colorful horse race held twice a year in Piazza del Campo. Here, the driver-guide leads a walk through the medieval streets, sharing stories of the city’s history and traditions. You can explore Siena’s cathedral and appreciate its Gothic architecture. The personalized guidance ensures you see the city’s highlights at your own pace, with ample time to soak in the atmosphere of this historic town.

Next, the tour heads to San Gimignano, renowned for its medieval towers built by wealthy families of the past. Visitors can walk leisurely through the cobbled streets, admire Gothic and Romanesque buildings, and climb the Torre Grossa for stunning panoramic views. The main square, Cistern Square, is perfect for taking photographs and enjoying the picturesque scenery. The admission to the cathedral is free, and the atmosphere here embodies the charm of Tuscany’s medieval period.

The tour includes a visit to a local winery, where guests enjoy a wine tasting session. The winery offers a chance to sample regional wines, with generous servings that are noticeably larger than standard tastings, as noted by some reviews. The wine selection is described as reasonable and well-curated, providing insight into Tuscany’s viticultural traditions. The tasting is paired with local produce, making it a true culinary highlight of the day.

Included in the tour is a traditional Tuscan lunch, served at the first winery or an adjacent location. The lunch typically features cheese, salami, and prosciutto, shared among two persons, resembling a sampling platter rather than a full sit-down meal. Some reviews note that this lunch provides a relaxed tasting experience but may not be a substantial meal for everyone. It’s a good idea to arrive hungry or supplement with snacks if needed.
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After a full day of exploration, the return journey to Florence follows a scenic route, offering spectacular views of rolling hills, vineyards, and charming villages. The drop-off point is back at Piazza della Repubblica around 5 pm, giving travelers plenty of time to relax or continue exploring Florence afterward.

The meeting point is centrally located in Florence at Piazza della Repubblica, a spot that’s near public transportation and easy to access. The transport is in a luxurious, air-conditioned Mercedes vehicle, ensuring comfort during the approximately 9-hour trip. This private tour guarantees that only your group participates, creating a personalized experience free from the pressures of large groups.

This tour shines in its small-group format, with driver-guides who provide insider stories and tailored attention. The driver-guide in Siena adds a personal touch to the city walking tour, making the experience more engaging and informative. The expert guides’ knowledge about Tuscany’s history, art, and architecture enriches the visit.
The tour operates rain or shine, so travelers should dress appropriately for weather conditions. Since all passengers pay the same rate, regardless of age, it’s best suited for adults and older children. The timing can occasionally fluctuate, especially if stops run longer or shorter, but the overall schedule is flexible enough to maximize sightseeing and tasting opportunities.
The private nature combined with personalized attention makes this tour stand out. The inclusion of wine tasting and a Tuscan lunch in a scenic setting adds to its value, offering a taste of Italy beyond just sightseeing. The expert driver-guide and the scenic drive through the Tuscan countryside are major highlights, especially for those who appreciate comfort, culture, and cuisine.
“Our guide Yaris was the best. He was so knowledgeable and gave us the experience of our lives. My 16 year old daughter thought this was the highli…”
How long is the tour?
The tour lasts approximately 9 hours, from 8 am to around 5 pm.
What are the main stops?
Stops include Siena and San Gimignano, with a wine tasting and a lunch at a local winery.
Is the tour private or in a group?
This is a private tour, with only your group participating, ensuring personalized service.
What type of vehicle is used?
Travel is in a luxurious Mercedes A/C minivan or similar vehicle.
Does the tour include lunch?
Yes, a traditional Tuscan lunch with cheese, salami, and prosciutto is included.
Is there a wine tasting?
Yes, there is a wine tasting at a carefully selected winery, with generous servings.
Can I cancel for a refund?
Yes, free cancellation is available up to 24 hours before the start.
Is the tour suitable for children?
Most travelers can participate, but children must be accompanied by an adult.
What is the meeting point?
The tour starts at Piazza della Repubblica in Florence.
Are tips included?
Tips are not included; gratuities are at your discretion.
What should I bring?
Wear comfortable clothing and shoes, especially for walking in towns and climbing towers. Dress appropriately for weather conditions.
Is gratuity expected?
Tipping is at your discretion, based on your satisfaction with the service.
This Private Best of Tuscany Hill Towns Tour offers a well-rounded glimpse into Tuscany’s historic towns, scenic vistas, and renowned wines. Its small-group format and personal guides make for an engaging and comfortable day out, especially suited for those seeking an intimate, curated experience of Italy’s iconic landscapes and culture.