Discover the enchanting allure of Siena and the picturesque Chianti countryside on this captivating private tour from Florence. Uncover the rich cultural heritage of Siena as you explore its iconic landmarks, including the stunning Duomo and the majestic Piazza del Campo. Indulge in the flavors of the region with two delightful wine tastings and a delicious local lunch, all while immersed in the charming medieval atmosphere. This tour promises to transport you to the heart of Tuscany, leaving you eager to uncover more of its captivating wonders.
Key Points
- Private tour from Florence to Siena and Chianti countryside, with hotel pickup/drop-off and an air-conditioned vehicle.
- Tour includes two wine tastings at different wineries in Chianti and a delicious local lunch.
- English-speaking driver provides basic commentary, while participants explore Siena’s historic center at their own pace.
- Tour is not wheelchair accessible, but most can participate with some navigation of short distances and uneven terrain.
- Customizable private tour experience focused on providing a convenient and enjoyable exploration of the region.
Tour Overview

This private tour from Florence takes visitors to the historic city of Siena and the picturesque Chianti countryside. Priced from $1,010.79 per person, it includes hotel pickup and drop-off, an air-conditioned vehicle, and a dedicated local guide.
Guests will enjoy two wine tastings at different wineries and an included lunch. While the driver provides basic commentary, they can’t leave the vehicle. The tour is private, but it can be modified if requested at booking.
Participants must be at least 18 years old for the wine tastings, which aren’t mandatory – soft drinks are available instead. The tour isn’t wheelchair accessible, but most travelers can participate.
You can also read our reviews of more tours and experiences in Florence
Inclusions

Although the tour from Florence to Siena and the Chianti countryside includes hotel pickup and drop-off, an air-conditioned vehicle, and a dedicated local guide, the inclusions don’t stop there.
Travelers will enjoy two wine tastings at different wineries in the Chianti region and a delicious included lunch.
For families, there’s even an infant seat available upon request.
While tipping isn’t mandatory, it’s appreciated by the hardworking driver and guide.
Whether you’re seeking a cultural experience or simply want to indulge in the region’s renowned wines, this tour offers a well-rounded itinerary that caters to a variety of interests.
Driver and Tour Guide Information

The professional English-speaking driver provides basic commentary from the vehicle, though they can’t leave the car to walk around with you.
This is a private tour that includes only your group, and the driver can’t accompany you on any walking portions of the experience.
However, the tour can be modified or customized if requested at the time of booking. This allows for a more personalized experience to suit your preferences.
While the driver isn’t able to join you on foot, they remain available to transport you between the various stops on the tour, ensuring a seamless and convenient experience.
Wine Tasting and Age Restrictions

During the tour, guests have the opportunity to partake in two wine tastings within the Chianti countryside. The minimum drinking age for the wine tastings is 18 years old. For underage travelers, soft drinks are available as an alternative. Tipping the wineries is not included in the tour price but is appreciated, though not mandatory. The wine tasting experience allows guests to savor the renowned flavors of the Chianti region and learn about the winemaking process from local experts.
| Wine Tasting | ||
|---|---|---|
| Location | Chianti Area | Chianti Area |
| Duration | 30 minutes | 30 minutes |
| Focus | Winery 1 | Winery 2 |
Accessibility and Participation

This tour isn’t wheelchair accessible. Most travelers, however, can participate in this excursion.
Guests should be able to get in and out of the vehicle and walk short distances over uneven terrain. The wineries and historical sites visited may have steps or cobblestone paths.
While the tour provider does their best to accommodate diverse needs, the itinerary may not be suitable for those with significant mobility issues. Guests should consult with the tour provider prior to booking if they’ve any concerns about their ability to fully participate.
The provider aims to ensure all guests have an enjoyable and memorable experience on this private tour of Siena and Chianti.
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Exploring Siena’s Historic Center

Travelers embark on a journey through Siena’s historic center, seeing the city’s rich cultural heritage.
The tour explores the Piazza del Campo, renowned for its distinctive shell-like shape and the Palazzo Pubblico, an impressive Gothic-style town hall. Visitors marvel at the intricate marble striations of the Duomo di Siena, a stunning cathedral that showcases Sienese Romanesque-Gothic architecture.
The group meanders through the charming medieval streets, admiring the quaint shops, cafes, and historic landmarks that dot the landscape.
Key highlights include:
- Piazza del Campo
- Palazzo Pubblico
- Duomo di Siena
- Charming medieval streets
- Quaint shops and cafes
Discovering Chianti’s Picturesque Countryside
After exploring the historic center of Siena, the tour continues into the picturesque Chianti countryside. Guests will experience two wine tastings at family-owned wineries, learning about the region’s renowned Sangiovese grapes and unique winemaking traditions. Between tastings, they’ll enjoy a delightful lunch featuring local Tuscan specialties. The rolling hills, cypress-lined roads, and medieval hilltop towns of Chianti create a quintessential Italian landscape that captivates all who visit.
| Winery 1 | Winery 2 |
|---|---|
| Family-owned | Family-owned |
| Sangiovese grapes | Sangiovese grapes |
| Traditional methods | Traditional methods |
| Estate tour | Estate tour |
Indulging in Tuscan Cuisine and Wines
Guests indulge in the flavors of classic Tuscan cuisine during a delightful lunch included in the tour.
The lunch showcases the region’s renowned culinary traditions, featuring a selection of rustic, homemade dishes that highlight the finest local ingredients.
Complementing the meal are two wine tastings at different Chianti wineries, where guests have the opportunity to savor the region’s acclaimed wines.
The tasting experience allows them to appreciate the nuances and complexities of these celebrated vintages.
The tour seamlessly blends the gastronomic and oenological delights of Tuscany, immersing guests in the essence of this renowned food and wine destination.
- Authentic Tuscan cuisine
- Homemade regional dishes
- Two Chianti wine tastings
- Appreciation of local vintages
- Seamless culinary experience
Since You Asked
What Are the Pickup and Dropoff Locations for the Tour?
The tour includes hotel pickup and dropoff, providing convenient transportation to and from the tour locations. Guests are picked up from their Florence hotels and dropped off at the same location at the end of the tour.
How Long Is the Total Duration of the Tour?
The total duration of the tour is not explicitly stated. However, the overview indicates it includes hotel pickup and dropoff, a 2-hour guided tour, and two wine tastings, suggesting the full tour likely lasts approximately 5-6 hours.
Are There Any Additional Costs Not Included in the Price?
The price listed includes hotel pickup and dropoff, a driver, a guide, two wine tastings, and lunch. There are no additional costs mentioned, though tipping for the guide and driver is not included but appreciated.
Can We Request a Different Language for the Tour Guide?
Yes, the tour can accommodate different language requests for the guide. Clients can inquire about availability and any additional fees when booking the tour.
Are There Any Dress Code Requirements for the Wine Tastings?
There are no specific dress code requirements for the wine tastings on this tour. Participants should wear comfortable, casual attire that’s appropriate for both the winery visits and the overall sightseeing activities during the tour.
Siena and Chianti Country With Lunch&2winetastings From Florence
The Sum Up
This private tour from Florence offers an enchanting experience that allows visitors to enjoy the rich cultural heritage of Siena and the picturesque Chianti countryside. With two delightful wine tastings, a delicious local lunch, and convenient transportation, it’s an ideal way to discover the best of this captivating region. Whether you’re interested in exploring historic sites or savoring Tuscan flavors, this tour has something to delight every traveler.






















