Exploring the enchanting Tuscan countryside on a day trip from Florence promises an immersive experience. Visitors can uncover the Gothic splendor of Siena, marvel at the iconic tower houses of San Gimignano, and savor the flavors of Chianti wine in the rolling hills. This private tour offers a chance to explore the region’s rich history and stunning architecture, all while indulging in the local cuisine. From the charming medieval town of Monteriggioni to the panoramic vistas, this Tuscan adventure is sure to captivate the senses.
Key Points

- This private tour provides a comprehensive exploration of Siena, Monteriggioni, and San Gimignano, allowing visitors to experience the Gothic architecture and rich history of Tuscany.
- The tour includes scenic drives through the renowned Chianti wine region, with an optional stop at a local farm for an immersive culinary experience.
- Visitors can marvel at the iconic Siena Cathedral, Piazza del Campo, and the well-preserved medieval architecture throughout the cities.
- The tour offers a leisurely stop in Monteriggioni, where guests can savor local cuisine and Chianti wine while exploring the town’s defensive walls.
- San Gimignano’s distinctive tower houses, which reflect the town’s prosperous past, provide a visually stunning and historically captivating experience for travelers.
Tour Overview

The Siena, San Gimignano and Chianti Day Trip from Florence is a comprehensive tour that allows visitors to explore the charming medieval towns and picturesque countryside of Tuscany.
Priced at Kč 25,032 for up to 4 people, the 8-hour private tour is available in multiple languages and offers complimentary hotel pickup and drop-off in Florence.
Guests will discover the Gothic architecture of Siena, visit the hilltop town of Monteriggioni, and wander the iconic tower houses of San Gimignano.
Along the way, they’ll enjoy scenic drives through the renowned Chianti wine region.
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Exploring the Gothic City of Siena

Although renowned for its Gothic architecture, Siena’s Piazza del Campo steals the show as the conch-shaped heart of the city. Surrounded by grand palaces, this medieval marketplace hosts the famous Palio horse race twice a year.
Nearby, the 13th-century Siena Cathedral impresses with its ornate façade and intricate interiors. Visitors can explore the cathedral’s museum and climb its bell tower for panoramic city views.
With a licensed guide, travelers discover Siena’s rich history, from its Roman origins to its time as a powerful medieval commune. From the Campo to the cathedral, Siena captivates with its well-preserved Gothic splendor.
Visiting Monteriggioni for Lunch

After exploring the captivating Gothic architecture of Siena, the tour moves on to Monteriggioni, a quaint medieval town nestled amid the rolling Tuscan hills.
Visitors enjoy a one-hour stop to wander the town’s intact defensive walls and admire the historic buildings. Many opt for a leisurely lunch at one of the charming restaurants or cafes, savoring local cuisine and Chianti wine.
This peaceful interlude provides a welcomed respite before continuing the day’s adventures in San Gimignano and the Chianti countryside. The picturesque town offers a glimpse into Tuscany’s storied past.
Optional Lunch at Tenuta Casanova Farm
Alternatively, visitors can opt for a more immersive culinary experience with an optional lunch at the Tenuta Casanova farm.
On the farm, guests will savor organic, locally-sourced products paired with the region’s renowned Chianti wines. The farm lunch reduces time in the cities but offers an opportunity to appreciate Tuscan cuisine and winemaking traditions firsthand.
Visitors pay the farm directly for this optional activity. While it cuts into sightseeing, the farm lunch provides a memorable, authentic taste of Chianti that complements the tour’s historical and scenic highlights.
More Great Tours NearbyDiscovering San Gimignano’s Tower Houses

The iconic tower houses of San Gimignano stand as enduring testaments to the town’s prosperous medieval past. Once numbering 72, these distinctive towers were built by rival noble families to showcase their wealth and power.
Today, 14 towers remain, their spires punctuating the skyline. Visitors can wander the town’s winding streets, marveling at the remarkably well-preserved medieval architecture.
From the top of the tallest tower, the Torre Grossa, panoramic views stretch across the rolling Tuscan countryside. With its unique silhouette and history, San Gimignano captivates travelers seeking a glimpse into Italy’s storied past.
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Driving Through the Chianti Hills

As the tour moves on from the captivating town of San Gimignano, the drive through the Chianti hills offers a scenic transition.
Lush vineyards and olive groves dotted across the rolling landscape create a quintessential Tuscan backdrop. Winding roads lead the private Lamborghini Urus through picturesque villages, where visitors can catch glimpses of medieval architecture and local life.
The drive provides a chance to admire the area’s natural beauty, with panoramic views of the surrounding countryside. This leg of the tour allows travelers to soak in the essence of the Chianti region before arriving at their final destination.
Inclusions and Exclusions

This Siena, San Gimignano and Chianti Day Trip from Florence includes a range of services to enhance the overall experience.
The package includes hotel pickup and drop-off in Florence, bottled water, a private guide in Siena and a wine cellar, as well as lunch (unless opting for the farm visit).
Plus, museum and church entry fees are covered, and gratuities are included.
However, the cost of entry to the Tenuta Casanova farm and optional lunch there aren’t part of the package price.
Guests should also note that the tour is limited to a maximum of 4 people per booking.
Important Information

Maximum of 4 people can be accommodated per booking for this tour.
It’s not suitable for individuals with mobility impairments, so those with special needs should consider alternative options.
Guests are advised to bring sunglasses and wear comfortable shoes for the day’s activities.
Unfortunately, pets aren’t allowed on this tour.
The drivers are knowledgeable about Tuscany and local traditions, ensuring a memorable experience for all participants.
Given the feedback about no-shows, it’s recommended to confirm the booking and pickup details well in advance to avoid any issues on the day of the tour.
The Sum Up

This Siena, San Gimignano, and Chianti Day Trip from Florence offers a captivating journey through Tuscany’s historic gems. Visitors will enjoy the Gothic splendor of Siena, savor local cuisine and Chianti wine in Monteriggioni, and explore the iconic medieval tower houses of San Gimignano. Driving through the picturesque Chianti hills completes this unforgettable experience, showcasing the region’s unparalleled beauty and charm.
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