Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

A private day trip from Florence to Tuscany offers a thoroughly curated experience that highlights some of Italy’s most iconic towns and landscapes. Priced at $801.14 per group (up to 7 people), this tour provides a personalized journey with a knowledgeable private driver and luxury transport. It lasts approximately 8 hours, starting at 9:30 am, with convenient pickup in downtown Florence. Visitors can expect to explore Siena’s Piazza del Campo and Siena Cathedral, wander the medieval streets of San Gimignano, and drive through the scenic Chianti wine region, with optional wine tasting and a winery lunch.

This tour is especially appealing for those seeking an intimate, flexible experience with a focus on small towns, stunning views, and local food and wine. While generally praised for the expert guidance and beautiful scenery, some reviews mention occasional delays or the need to choose between sightseeing and winery visits. This tour suits travelers who want a relaxed, customized day exploring Tuscany’s highlights with up to 7 guests.

Key Points

• Private 8-hour Tuscany experience from Florence, ideal for groups up to 7
• Visits Siena, including Piazza del Campo and Siena Cathedral
• Explores San Gimignano’s medieval towers and historic streets
• Drives along the Chianti Wine Road, with options for wine tasting and lunch at a vineyard
• Luxury vehicle, private driver, and onboard Wi-Fi included
• Most bookings are made 66 days in advance, indicating high demand

Tuscany in a Private Luxury Minivan

This private tour departs from Florence with pickup arranged in the city’s downtown area, making it straightforward to start your day. The vehicle is air-conditioned, and Wi-Fi can be requested onboard for a more connected experience. The tour lasts about 8 hours, offering a flexible schedule that balances sightseeing with leisure.

Traveling in a luxury minivan, you will enjoy the scenic drive through Tuscany’s famous Chianti hills. The private driver is well-versed in local stories, traditions, and history, sharing insights throughout the journey. The personalized nature of the tour means the vehicle and time allocation are tailored specifically to your group’s preferences, making it ideal for those who value comfort and exclusivity.

Exploring Siena’s Medieval Charm

The tour’s first major stop is Siena, renowned for its medieval architecture. Visitors are led through the historic streets to see landmarks such as the famous Conch-shaped Piazza del Campo, where the iconic Palio horserace takes place annually. The Siena Cathedral, a 13th-century masterpiece, is also on the itinerary.

In two hours, you have the chance to stroll the cobblestone streets, shop for local food and gift items, and admire the town’s authentic medieval atmosphere. The admission to the cathedral and piazza is free, allowing you to focus on soaking in the ambiance at your own pace.

San Gimignano’s Towering History

The journey continues to San Gimignano, a medieval hilltop town famous for its towers that date back to the 1300s. Spending approximately two hours here, visitors explore the historic center, marvel at the well-preserved towers, and enjoy spectacular views of the Tuscan countryside.

San Gimignano’s architecture feels like stepping into a medieval painting, with narrow streets and towers that seem to reach the sky. The town’s charm is complemented by the chance to browse local shops and immerse in its timeless atmosphere.

Driving Through Chianti’s Scenic Vineyards

A highlight of this private tour is the drive along the Chianti Wine Road, offering stunning panoramic views of vineyards and rolling hills. This scenic route provides plenty of opportunities for photo stops and appreciating the Tuscan countryside.

There is an option to visit a local vineyard for wine tasting and a farm or winery lunch, which typically costs between €50-€70 per adult and involves sampling Chianti wines, balsamic vinegar, and local foods. Choosing this option means less time in Siena and San Gimignano but offers an authentic taste of Tuscan viticulture.

Visiting Castellina in Chianti or Monteriggioni

Depending on your preferences, the tour can include a stop at Castellina In Chianti, a charming town known for its organic local products and wine. Alternatively, some groups may opt to visit Monteriggioni, a medieval fortress renowned for its ancient walls and towers.

If you select the vineyard lunch, the itinerary excludes Monteriggioni, focusing instead on the wine experience. This flexibility allows your group to prioritize culinary delights or historical sites.

The Charm of San Gimignano’s Old Town

The last stop before returning to Florence is San Gimignano’s historic center. Here, visitors spend about two hours wandering medieval streets, admiring the towers, and enjoying local gelato or shopping. The town’s 1300s architecture transports visitors to a different era, with plenty of photo opportunities and a relaxed pace.

This stop offers a perfect balance of exploration and leisure, with free admission to most spots, allowing you to absorb the timeless ambiance.

Logistics: Pickup, Route, and Comfort

Pickup in Florence is included, with the luxury vehicle being air-conditioned and equipped with Wi-Fi upon request. The driver acts as a guide, sharing curiosities and traditions about Tuscany along the way.

The itinerary typically includes about two hours in Siena, two hours in San Gimignano, and a scenic drive with optional wine tasting. The timing ensures you experience each location thoroughly while maintaining a relaxed and unhurried pace.

The tour is designed for up to 7 guests, offering an intimate experience that feels personalized and flexible. It’s suitable for those who enjoy comfortable transportation and avoiding large group crowds.

Potential Limitations and Considerations

While most reviews praise the knowledgeable guide and stunning views, some mention delays or less time in certain locations if opting for the winery lunch. For instance, choosing the winery lunch reduces the exploration time in Siena and San Gimignano, but offers the benefit of wine tasting and local food.

Plus, lunch and wine tastings are not included in the base price and cost approximately €50-€70 per adult, payable on spot. Some reviews also highlight that lunch can be more expensive than expected.

Finally, booking in advance—generally 66 days ahead—is recommended due to high demand, especially during peak seasons.

Who Will Enjoy This Tour Most?

This private Tuscany tour is best suited for small groups seeking an exclusive, relaxed experience with a personal driver and guide. It appeals most to travelers who value comfort, flexibility, and personalized insights. Wine lovers will appreciate the wine tasting option, while those interested in medieval towns will find the stops at Siena and San Gimignano particularly memorable.

It caters to up to 7 guests, making it an ideal choice for families, friends, or couples wanting a more intimate day outside Florence. The scenic drives, historic sites, and local food make it a well-rounded overview of Tuscany’s highlights.

The Overall Experience of the Tuscany Private Day Trip

This tour provides a comprehensive and comfortable way to see Siena, San Gimignano, and the Chianti wine region without the hassle of self-driving or big groups. The private driver ensures a smooth, personalized journey, with insights into local traditions.

While some may prefer more time at each stop or a different combination of sites, the flexibility and luxury transport stand out. The reviews reinforce that this tour is highly recommended for those seeking a special day in Tuscany, with many calling it the highlight of their trip.

Frequently Asked Questions

What is included in the tour price?
The private transfer, luxury vehicle, hotel pickup and drop-off in Florence, bottled water, and Wi-Fi on request are included. Wine tasting and lunch are optional extras payable on spot.

How long is the tour?
The tour lasts approximately 8 hours, starting at 9:30 am and ending in the late afternoon or early evening.

What are the main stops on this tour?
Stops include Siena, San Gimignano, and a scenic drive through Chianti, with a possible vineyard visit and lunch.

Is the tour suitable for children or elderly?
Yes, the luxury vehicle and short walking distances at each stop make it accessible for most age groups, though comfortable shoes are recommended.

Can I customize the itinerary?
The tour is private and customizable; discussions with the driver about preferred stops or activities are possible.

What is the cancellation policy?
Free cancellation is available up to 24 hours in advance. Cancellations less than 24 hours before the start are not refundable.

Are meals included?
No, lunch and wine tasting are not included in the base price, but can be added for an additional €50-€70 per adult.

How far in advance should I book?
Most bookings are made around 66 days ahead, reflecting high demand, especially during peak seasons.

What makes this tour stand out?
The personalized service, scenic drives, expert driver, and flexibility to include wine tasting or skip certain sites make this a well-rounded Tuscany experience.

Is this tour suitable for large groups?
No, it’s designed for up to 7 guests, ideal for small groups seeking exclusivity.