Setting out on a private tour from Florence is an excellent way to discover the enchanting cities of Siena, San Gimignano, and the picturesque Chianti wine region. Over the course of eight hours, visitors can enjoy the historic charm of these Tuscan gems, marveling at iconic landmarks, savoring regional flavors, and experiencing the breathtaking countryside. With a guided walking tour and scenic drives, this excursion promises a rich cultural exploration that’ll leave travelers eager to uncover more of Tuscany’s treasures.
Key Points

- This private full-day tour from Florence takes visitors to the historic cities of Siena, San Gimignano, and the Chianti wine region.
- The tour includes guided walking tours of the UNESCO-listed Siena’s historic center, highlighting iconic landmarks like the Piazza del Campo and the Siena Cathedral.
- Guests will enjoy a scenic drive through the picturesque Chianti countryside, with breathtaking views of vineyards, olive groves, and charming stone farmhouses.
- The tour also includes a visit to the well-preserved 13th-century fortified hamlet of Monteriggioni and the historic town of San Gimignano, known for its medieval towers.
- The tour is led by an expert guide and includes transportation in a private, air-conditioned vehicle, with a duration of over 8 hours and a cost of $546.21 per person.
Tour Overview

This private full-day tour from Florence whisks visitors to the historic cities of Siena, San Gimignano, and the Chianti wine region.
Over 8 hours, guests explore Siena’s medieval center, discover the famous Piazza del Campo, and enjoy a scenic drive through Chianti’s vineyards and olive groves.
Guests explore Siena’s medieval center, discover the famous Piazza del Campo, and enjoy a scenic drive through Chianti’s vineyards and olive groves.
The tour also includes free time in the UNESCO-listed San Gimignano and a visit to the fortified hamlet of Monteriggioni.
Transport is via a private, air-conditioned vehicle, and an expert guide provides insights throughout the journey.
The tour costs $546.21 per person and offers free cancellation up to 24 hours in advance.
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Exploring Siena’s Historic City Center

As guests arrive in Siena, they’re immediately captivated by the city’s historic charm.
The private guide leads them on an informative walking tour, highlighting three key sights:
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Piazza del Campo – One of the world’s most stunning medieval squares, featuring the iconic Palazzo Pubblico and its bell tower.
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Siena Cathedral – A magnificent Gothic cathedral with breathtaking marble façades and interiors adorned with priceless works of art.
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Libreria Piccolomini – A stunning Renaissance library housing exquisite frescoes and manuscripts.
Guests are enchanted by Siena’s well-preserved architecture, vibrant culture, and rich history as they explore this UNESCO World Heritage Site.
Discovering Piazza Del Campo

Dominating the heart of Siena, the iconic Piazza del Campo captivates visitors with its striking semicircular design and stunning medieval architecture.
Twice a year, the Palio horse race takes place in this remarkable square, drawing crowds from around the world.
Lined with cafes and historic buildings, Piazza del Campo is considered one of the world’s most beautiful public spaces.
Visitors can admire the magnificent Palazzo Pubblico and its iconic bell tower, the Torre del Mangia, which offers panoramic views over the city.
This vibrant square is the perfect place to soak in Siena’s rich history and lively atmosphere.
Scenic Drive Through Chianti Countryside

What better way to experience the beauty of the Chianti countryside than on a scenic drive through its rolling hills and picturesque vineyards?
During your tour, you’ll be treated to breathtaking views of:
Breathtaking views of endless vineyards, quaint stone farmhouses, and glistening olive groves in the Tuscan countryside.
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Endless rows of lush, verdant vineyards stretching as far as the eye can see.
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Quaint stone farmhouses and charming medieval villages nestled among the vines.
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Gently undulating olive groves, their silvery leaves glistening in the Tuscan sun.
Sit back, relax, and soak in the quintessential Italian countryside as you wind your way through this picturesque region, a true feast for the senses.
More Great Tours NearbyVisiting Monteriggioni

Why does Monteriggioni stand out as a unique stop on this private tour? The 13th-century fortified hamlet enchants visitors with its well-preserved medieval architecture. Strolling along the town’s walls, you’ll be transported back in time. The stunning backdrop of the Chianti countryside only adds to Monteriggioni’s charm.
| Feature | Description |
|———|————-|
| Walls | Intricately preserved medieval walls surrounding the town |
| Towers | 14 stone towers dotting the walls, each with their own character |
| History | Founded in the early 13th century as a defensive outpost |
This peaceful respite offers a glimpse into Tuscany’s storied past, complementing the other highlights of the day’s adventure.
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Exploring San Gimignano

As you continue the private tour, the historic town of San Gimignano comes into view. Perched atop a hill, its iconic medieval towers pierce the sky.
You’ll be enchanted by San Gimignano’s well-preserved architecture and charming piazzas. Spend time exploring:
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The imposing Piazza del Duomo, home to the impressive Cathedral of Santa Maria Assunta.
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The quaint Piazza della Cisterna, with its unique triangular shape and ancient well.
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The artisanal shops and family-owned wineries that line the narrow streets, offering a glimpse into the town’s vibrant culture.
With its stunning natural setting and captivating history, San Gimignano is a true highlight of the tour.
Transportation and Logistics

The tour includes pickup from your centrally located hotel in Florence at 9:00 AM, ensuring a seamless start to your day.
You’ll travel in a deluxe, air-conditioned vehicle equipped with on-board Wi-Fi, allowing you to stay connected throughout the journey.
Your expert, multilingual guide will provide commentary in English, German, Italian, French, and Spanish, enriching your understanding of the sights.
While the driver will offer general introductory information, they aren’t licensed to guide you through city centers, museums, or churches.
Please note this tour may not be suitable for individuals with mobility impairments.
Inclusions and Important Information

What exactly does the tour include? The private tour from Florence to Siena, San Gimignano, and Chianti includes:
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A private local professional guide in Siena for 2 hours, providing a deeper dive into the historic city center.
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Entrance fees for the Siena Cathedral, Libreria Piccolomini, and Museo dell’Opera Metropolitana, allowing you to fully learn about the city’s architectural and cultural treasures.
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However, the tour doesn’t cover gratuities, food, or beverages, so you’ll have the freedom to explore the local cuisine at your own pace.
It’s important to note that the driver provides general introductory information but isn’t a licensed guide for city centers, museums, or churches.
Plus, the tour may not be suitable for individuals with mobility impairments.
The Sum Up

This private tour from Florence offers a comprehensive and captivating Tuscan experience. Visitors will enjoy the rich history and stunning landscapes of Siena, San Gimignano, and the Chianti region. From the iconic Piazza del Campo to the charming medieval towns, this tour provides a rich and memorable exploration of the heart of Tuscany.
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