Private Full-Day Tour: Siena, San Gimignano & Chianti4.8(3,003 Reviews)9 hours
From€170.00per person
Listing ID : 63753
4.8(3,003 Reviews)
Private Full-Day Tour: Siena, San Gimignano & Chianti
9hDuration
Max 12 peopleGroup Size
English, ItalianSpeaking Guide
Mobile ticketAccepted
About this experience
Duration9 Hours
Group SizePrivate
Starts AtFlorence
LanguagesEnglish, Italian
Private Full-Day Tour from Florence
Siena, Monteriggioni, San Gimignano & Chianti Wine Tasting
A private journey through Tuscany's medieval towns, hilltop fortresses, and celebrated wine country
This private Tuscany day tour from Florence takes you through four of the region's most celebrated destinations in a single, well-paced itinerary. Travel in comfort across rolling hills, ancient stone streets, and sun-drenched vineyards without the distraction of a large group.
The day moves between Monteriggioni's intact medieval walls, Siena's UNESCO-listed historic center, and the vine-covered landscapes of the Chianti Classico zone. Each stop offers a distinct character — military architecture, Gothic urban planning, and centuries-old winemaking tradition side by side.
San Gimignano rounds out the experience with its cluster of medieval towers and one of Italy's most recognized gelaterias. The pace is relaxed, the route is private, and the setting is consistently Tuscan at its most photogenic.
Tour Highlights
Walk the ancient walls of Monteriggioni, one of Italy's best-preserved medieval fortified villages.
Explore Siena's UNESCO-listed historic center, including the iconic Piazza del Campo and the Gothic Cathedral.
Enjoy a guided wine tasting at a Chianti winery, featuring local varieties including Chianti Classico.
Sit down to a traditional Tuscan lunch prepared with fresh, locally sourced ingredients at the winery.
Discover San Gimignano's medieval towers and the lively Piazza della Cisterna, a UNESCO World Heritage Site.
Travel the scenic Chianti countryside in a private vehicle with no shared itinerary constraints.
Itinerary
1
Monteriggioni
Your first stop is Monteriggioni, a circular hilltop village encircled by a complete medieval wall dating to the 13th century. Walk the perimeter, take in panoramic views of the Sienese countryside, and explore the quiet interior of this remarkably intact fortress village.
2
Siena Historic Center
Siena's UNESCO-listed city center rewards unhurried exploration. The visit centers on Piazza del Campo — the distinctive shell-shaped square famous for the Palio — and the Cathedral of Siena, a landmark of Italian Gothic architecture with an optional interior entry.
3
Chianti Winery: Tasting and Lunch
At a winery in the Chianti Classico zone, a guided tasting introduces you to the region's signature wines. A traditional Tuscan lunch follows, featuring seasonal ingredients prepared in the local style.
4
San Gimignano
The afternoon visit to San Gimignano focuses on Piazza della Cisterna and the medieval tower skyline that defines this UNESCO-listed town. Time is available to browse artisanal shops or stop at Gelateria Dondoli, internationally recognized for its award-winning gelato.
5
Return to Florence
The return drive across the Tuscan countryside brings the day to a relaxed close. You arrive back in Florence at the end of a full itinerary covering four distinct destinations.
What Is Included
Included
Private transportation from and to Florence
Professional private guide throughout the day
Guided wine tasting at a Chianti winery
Traditional Tuscan lunch at the winery
Entrance to Monteriggioni village
All transfers between stops
Not Included
Siena Cathedral interior entry (optional, paid on site)
Personal expenses and souvenirs
Gratuities for the guide and driver
Any food or drinks beyond those specified
Important Information
This is a private tour. The itinerary, pace, and stops are dedicated exclusively to your group. Please review the details below before booking.
Duration
Approximately 9 hours, covering four destinations with travel time between each stop.
Meeting Point
Pickup is arranged from your Florence accommodation or a central Florence location confirmed at booking.
What to Bring
Comfortable walking shoes are recommended. Bring a light layer for visits to churches and cooler interior spaces. Sun protection is advisable in warmer months.
Cancellation
Cancellation terms are provided at checkout. Review the policy carefully before confirming your reservation.
Accessibility
The tour involves walking on cobblestone streets and uneven medieval surfaces. It may not be fully suitable for guests with significant mobility limitations. Contact the operator prior to booking if assistance is required.
Age Range
Suitable for all ages. The pace is relaxed and the difficulty level is easy. Children are welcome.
Reserve Your Private Tuscany Day Tour
Secure your spot on this private full-day tour and explore Siena, Monteriggioni, San Gimignano, and the Chianti wine country at your own pace. Availability is limited for private departures.
Is this tour suitable for first-time visitors to Tuscany?▼
Yes. The itinerary covers four of Tuscany's most iconic destinations in a single day, making it well suited to travelers who want a broad introduction to the region. The private format also allows the guide to adapt the pace and focus to your interests.
What type of wines are tasted at the Chianti winery?▼
The tasting features local varieties from the Chianti region, with a focus on Chianti Classico. The selection may vary depending on the winery's current offerings and the season of the visit.
Can I visit the interior of Siena Cathedral on this tour?▼
Cathedral entry is optional and not included in the tour price. You may choose to enter at an additional cost paid directly on site during the Siena stop.
How much walking is involved throughout the day?▼
The tour is rated easy, though each destination involves walking on cobblestone or uneven medieval surfaces. Comfortable, flat-soled shoes are recommended. The total walking distance is moderate and spread across multiple stops.
Is lunch included, and can dietary requirements be accommodated?▼
A traditional Tuscan lunch at the Chianti winery is included in the tour. If you have specific dietary requirements, notify the operator at the time of booking so arrangements can be made in advance.
What happens if the tour needs to be cancelled or rescheduled?▼
Cancellation and rescheduling conditions are detailed at checkout. It is recommended to review these terms before completing your reservation, as conditions may vary depending on notice period.
Tuscany Day TourSienaSan GimignanoMonteriggioniChianti Wine TastingPrivate TourFlorence ExcursionMedieval TuscanyTuscan LunchUNESCO SitesWine CountryFull Day Tour
This tour operates from Florence, the capital of the Tuscany region in central Italy, and covers four destinations within the provinces of Siena and Pisa. Monteriggioni and Siena are located in the Siena province, within the heart of the historic Val d'Elsa and Crete Senesi landscapes. The Chianti Classico wine zone, a denominazione d'origine controllata e garantita (DOCG) area, lies between Florence and Siena along the SR222 corridor. San Gimignano, situated in the province of Siena near the Elsa Valley, is a designated UNESCO World Heritage Site recognized for its preserved medieval tower house architecture. The entire route traverses the Tuscan Hills (Colline Toscane), a landscape characterized by cypress-lined roads, vineyard terraces, and fortified hilltop settlements that define the visual identity of inland Tuscany.
Region: Tuscany, Italy | Provinces Covered: Florence, Siena | Tour Type: Private Full-Day | Activity Category: Cultural, Gastronomy, Wine Tourism | UNESCO Sites Included: Siena Historic Centre, San Gimignano | Wine Zone: Chianti Classico DOCG | Difficulty: Easy | Departure City: Florence | Language: Multi-language (private) | Season: Year-round
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