Private Siena to Florence Chianti and San Gimignano Transfer Tour

A Private Journey Through Tuscany: Siena to Florence with Enchanting Stops

The Private Siena to Florence Chianti and San Gimignano Transfer Tour offers an intimate and flexible way to explore some of Tuscany’s most iconic sights. Priced at $905.65 per group (up to 6 people), this 7-hour journey features private transportation in an air-conditioned minivan, with pickup from your Siena accommodation and drop-off at your Florence hotel. The driver-guided tour includes live commentary, making it a comfortable yet enriching experience.

The appeal of this tour lies in its carefully curated stops, including Medieval Monteriggioni, the UNESCO-listed San Gimignano, and the picturesque Greve in Chianti. While no meals are included, the stops in these towns provide opportunities to browse local shops or enjoy authentic cuisine independently. The tour’s flexibility and personalized nature make it a great option for those seeking an easy, scenic introduction to Tuscany’s highlights.

Key Points

• Private, guided transfer in a comfortable minivan, perfect for up to 6 travelers
• Includes visits to Monteriggioni, San Gimignano, and Greve in Chianti
• Flexible schedule with stops for sightseeing, shopping, and strolling
• Total duration approximately 7 hours, with hotel pickup and drop-off included
• Best suited for travelers wanting a private, paced experience without the hassle of train travel
• Free cancellation available if canceled more than 24 hours in advance

Departing from Siena: Pickup at 9:30am with a Private Driver

The tour begins at 9:30am with a pickup from your Siena accommodation. The private driver-guide comes directly to your location, ensuring a smooth start to your Tuscan adventure. This personalized pickup allows for a flexible and relaxed start to the day, avoiding the constraints of group tours or public transportation.

Once on board, the first stop is the medieval fortress of Monteriggioni. Built by the Sienese in the 13th century, this town features a complete ring of walls and towers, offering a glimpse into Tuscany’s defensive architecture. Monteriggioni withstood many attacks from Florence and Volterra before surrendering in an act of reconciliation, making it a meaningful historical marker in the region.

Exploring Monteriggioni: A Medieval Fortress

Monteriggioni stands out as a well-preserved example of medieval fortress architecture. Its walls and towers are almost intact, making it an ideal spot for photos and a brief walk through history. The town’s history as a defensive site against Florence adds a layer of significance, and its well-preserved state provides a sense of stepping back in time. Visitors can enjoy wandering along the walls, soaking in views of the rolling Tuscan hills.

There’s no included entrance fee, but the visit offers an authentic experience of medieval Italy. The leisurely pace allows ample time to explore and absorb the atmosphere without feeling rushed.

San Gimignano: A UNESCO World Heritage Site

In the morning, the tour arrives at San Gimignano, a hill-top town renowned for its medieval towers that have survived for centuries. Recognized as a UNESCO World Heritage Site, this town is famous for its distinctive skyline and well-preserved medieval architecture. The imposing towers and city walls evoke a sense of history, while the artisanal boutiques and stores selling saffron—the town’s notable product—add a lively, local flavor.

Tourists have leisure time here to browse shops, admire the architecture, or enjoy the local gastronomy in one of the many restaurants (which are not included in the tour price). The town’s vibrant atmosphere is perfect for a relaxed exploration, with plenty of photo opportunities and cultural sights to discover.

Lunch and Leisure Time in San Gimignano

While the tour doesn’t include lunch, visitors often find plenty of options to savor Tuscan cuisine in San Gimignano’s eateries. This provides flexibility for personal tastes, whether that’s a quick gelato or a sit-down meal. The free time allows for shopping for local products such as saffron or handcrafted souvenirs, enhancing the experience beyond just sightseeing.

Salami and Saffron: The Flavors of San Gimignano

Besides sightseeing, San Gimignano is famous for its artisanal stores selling local goods, particularly saffron and red wine. The town’s artisan boutique scene flourishes amid the medieval streets, offering authentic Tuscan treats. This stop is ideal for those interested in both cultural history and culinary specialties.

The Scenic Drive Through Chianti: Greve and Montefioralle

After leaving San Gimignano, the tour continues through the Chianti Classico region, known for its vineyards and rolling hills. The panoramic roads provide stunning views of the Tuscan landscape, making the drive itself a highlight.

The first Chianti town visited is Greve in Chianti, famous for its oval-shaped square filled with artisans’ shops and wine stores. It’s also recognized as the hometown of the explorer Verrazzano. Visitors have free time here to stroll around, explore local wine shops, or admire the charming town square.

Next is the hamlet of Montefioralle, a small yet picturesque village that offers a quieter, authentic taste of rural Tuscany. Its narrow streets and historic buildings contribute a peaceful contrast to the busier towns.

Drop-Off in Florence: End of the Day

At the conclusion of the 7-hour tour, the private driver delivers travelers directly to their Florence hotel. This seamless transfer ensures a stress-free end to an enriching day, leaving time to enjoy the Florence evening or continue exploring on your own. The private transportation guarantees comfort and convenience, avoiding crowded buses or train schedules.

Who Will Most Appreciate This Tour?

This private transfer tour appeals to travelers seeking flexibility, comfort, and personalized service. The private vehicle and live commentary make it ideal for those who prefer a tailored experience without the constraints of a larger group. It’s especially suitable for small groups or couples who want to explore at their own pace and enjoy the historical and scenic highlights of Tuscany.

While the tour includes excellent stops, it does require independent dining during the free time in San Gimignano and Greve. Travelers should be prepared for moderate walking during sightseeing stops, though the pace is generally relaxed.

The Sum Up: A Practical and Personalized Tuscan Escape

The Private Siena to Florence transfer tour offers an efficient, enjoyable way to see some of Tuscany’s most notable spots in one day. The well-chosen stops—Monteriggioni, San Gimignano, and Greve in Chianti—showcase the region’s medieval architecture, culinary traditions, and scenic landscapes. The private guide and transportation give travelers a relaxed, personalized experience, making it especially appealing for those who value comfort and flexibility.

The tour’s 7-hour duration balances sightseeing, leisure, and scenic drives, making it a practical choice without feeling rushed. The cancellation policy is flexible, allowing peace of mind with full refunds if plans change.

This tour delivers great value for small groups wanting a well-organized, private introduction to Tuscany’s highlights. It’s perfect for those eager to explore without the hassle of public transport or large tour groups—especially if you love history, wine, and picturesque towns.

Frequently Asked Questions

Is lunch included in this tour?
No, lunch is not included. The tour provides free time in San Gimignano and Greve in Chianti, allowing visitors to choose their own dining options.

What is the starting time and location?
The tour begins at 9:30am with pickup from your Siena accommodation. The driver guides you through the day’s stops and drops you off in Florence at the end.

How many people can join this tour?
The tour is priced per group for up to 6 people, making it ideal for small groups or families seeking a private experience.

What is the duration of the tour?
The entire experience lasts approximately 7 hours, including sightseeing and leisure stops.

Can I cancel this tour?
Yes, full cancellation is available if canceled more than 24 hours in advance. The policy allows for a refund, providing flexibility if plans change.

Is this tour suitable for all travelers?
Most travelers can participate, as the tour is designed to be comfortable with private transportation and manageable walking at stops.