Exploring the charming towns of Tuscany is a must-do for many visitors to Italy. This private tour from Rome takes travelers on a journey through the region’s medieval landscapes, showcasing the iconic sights of San Gimignano and the stunning Duomo di Siena. But the highlight of the day might just be the guided winery visit, where guests can sample the renowned Chianti wines and indulge in local appetizers. With the convenience of private transportation and the option for free cancellation, this 12-hour adventure promises an immersive experience that’ll leave you craving more of Tuscany’s timeless allure.

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Key Points

This private tour from Rome takes visitors to the medieval towns of San Gimignano and Siena, as well as a local winery, over the course of 12 hours.
In San Gimignano, visitors can explore the town’s UNESCO World Heritage Site status, narrow alleyways, and well-preserved medieval architecture.
The winery visit includes a guided tour, sampling of 15 wine and olive oil varieties, and local appetizers to enhance the tasting experience.
Siena’s highlights include the iconic Piazza il Campo, the Duomo di Siena, and the opportunity to climb the Tower of Mangia for panoramic city views.
However, reviews indicate potential issues with last-minute changes, difficulty reaching the agency, rigid cancellation policies, and the quality of the winery experience not meeting expectations.

You can check availability for your dates here:

Tour Overview

This private tour from Rome takes visitors on a day-long exploration of the enchanting medieval towns of San Gimignano and Siena, as well as a winery visit.

The 12-hour tour departs from Piazzale della Stazione Tiburtina and is offered in English and Spanish. Priced at $1,220.47 per person, the tour provides private transportation and the opportunity to discover San Gimignano’s medieval architecture, Siena’s historic center, and a winery for a guided tour and tasting.

Free cancellation is available up to 24 hours in advance for a full refund.

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San Gimignano Exploration

Visitors embark on a captivating journey through San Gimignano’s medieval landscape, marveling at its well-preserved architecture and quaint walled streets.

They stroll through Piazza della Cisterna, a picturesque square lined with charming buildings and dominated by the imposing Torre Grossa, one of the town’s iconic medieval towers.

Wandering the narrow alleyways, they discover hidden corners, artisanal shops, and glimpses of the surrounding Tuscan countryside.

The tour offers an immersive experience, allowing guests to step back in time and appreciate the timeless beauty and architectural richness that have earned San Gimignano its status as a UNESCO World Heritage Site.

Winery Visit and Tasting

After exploring the medieval charm of San Gimignano, the tour continues with a guided visit to a local winery.

The group learns about the production of Chianti wine, a regional specialty. During the tasting, they sample 15 varieties of wine and olive oil, accompanied by local appetizers.

Visitors sample 15 varieties of Chianti wine and olive oil, accompanied by local appetizers, as they learn about the region’s renowned winemaking.

The experience allows visitors to deepen their understanding of Tuscan winemaking and appreciate the nuances of the region’s acclaimed vintages.

The winery tour provides a captivating interlude before the group heads to the historic city of Siena for the next leg of the day’s adventure.

Discovering Siena

From the winery, the group makes its way to the historic city of Siena.

The tour explores Siena’s medieval charm, starting in the renowned Piazza il Campo, a grand semicircular square where the biannual Palio horse race is held.

The group marvels at the Duomo di Siena, a stunning cathedral known for its ornate Gothic facade and intricate marble stripes.

They climb the 14th-century Tower of Mangia, offering panoramic views over the city’s terracotta roofs and winding streets.

With two hours to discover Siena’s delights, the group immerses themselves in the city’s timeless atmosphere before heading back to Rome.

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Transportation and Logistics

Private transportation is provided for the tour, with pick-up and drop-off at hotels in the city center.

The travel time includes:

4 hours to reach San Gimignano.
40 minutes to travel from San Gimignano to the winery.
2.5 hours to return to Rome.
Additional time is allocated for exploring each destination.

The tour’s starting point is Piazzale della Stazione Tiburtina, where participants should arrive 15 minutes before the scheduled departure time.

Comfortable shoes and weather-appropriate clothing are recommended for the day’s activities.

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Meeting Point and Attire

Where exactly does the tour start? The meeting point for this private tour is Piazzale della Stazione Tiburtina, 15 minutes before the scheduled departure time. Arriving early is recommended to ensure a smooth start to the day.

| Meeting Point | Attire |

| — | — |

| Piazzale della Stazione Tiburtina | Comfortable shoes |

| 15 minutes before departure | Weather-appropriate clothing |

| Recommended to arrive early | – |

Guests should wear comfortable shoes for walking and dress appropriately for the weather, as the tour involves outdoor exploration in historic towns. With these considerations in mind, the tour can begin promptly and safely.

Customer Reviews

Although the overall tour received a 3-out-of-5 rating from six reviewers, their feedback highlights some significant issues with the tour agency’s booking changes and cancellations.

Customers reported:

Last-minute changes to scheduled activities without adequate notice.
Difficulty reaching the agency to address concerns or make adjustments.
Frustration with the agency’s rigid cancellation policy, resulting in lost deposits.
Concerns about the quality and presentation of the winery experience compared to advertised descriptions.

Despite the positive aspects of the tour, these booking and logistical challenges appear to have significantly impacted customer satisfaction.

Booking Considerations

Based on the customer reviews, prospective travelers should carefully consider the booking process and cancellation policy when planning this private tour. The reviews indicate issues with changes and cancellations by the tour agency, so it’s crucial to understand the provider’s policies. Here are some key booking considerations:

| Booking | Cancellation |

|———|————-|

| Advance booking required | Full refund up to 24 hours before |

| Pick-up/drop-off options | Fees may apply for later changes |

| Minimum group size | Policies may vary by provider |

| Additional fees/taxes | Recommend travel insurance |

The Sum Up

This private tour from Rome offers a captivating journey through Tuscany’s medieval wonders. From the iconic skyline of San Gimignano to the grandeur of Siena’s Duomo, travelers will enjoy the region’s rich history and culture. The winery visit completes the experience, allowing guests to savor Chianti’s renowned flavors. With private transportation and flexible cancellation policies, this tour provides a seamless and memorable way to explore the charm of Tuscany.