Full-Day Tour from Florence: Siena, San Gimignano & Chianti4.7(26,099 Reviews)10 hours and 30 minutes
From€32.50per person
Listing ID : 50212
4.7(26,099 Reviews)
Full-Day Tour from Florence: Siena, San Gimignano & Chianti
10h 30mDuration
Max 12 peopleGroup Size
EnglishSpeaking Guide
Mobile ticketAccepted
About this experience
Duration10 hours 30 minutes
Group SizeSmall Group
Starts AtPiazzale Montelungo Bus Terminal, Florence
LanguagesEnglish
Full-Day Tour from Florence
Florence to Siena, San Gimignano, Monteriggioni and Chianti Wine Region with Wine Tasting
A curated journey through medieval Tuscany, from fortified hilltop towns to rolling vineyards.
This full-day tour from Florence through Tuscany takes you across the iconic Chianti hills to four distinct destinations, combining UNESCO-listed architecture, medieval history, and an authentic wine tasting experience at a working estate.
The route is carefully designed to give travelers a broad yet meaningful introduction to the Tuscan landscape and its most celebrated towns. Each stop has its own distinct character, from the compact walled village of Monteriggioni to the grand Gothic squares of Siena.
A professional guide accompanies the group throughout the day, providing context and local knowledge at every stop. The included walking tour of Siena adds a layer of depth that independent sightseeing alone cannot replicate.
The day closes at a Chianti wine estate where the producer walks guests through the winemaking process before the tasting begins. It is a fitting conclusion to a day spent moving through one of the most historically and culturally layered regions in Italy.
Tour Highlights
Guided walking tour of Siena, a UNESCO World Heritage Site, including Piazza del Campo and the Cathedral.
Visit Monteriggioni and its remarkably intact medieval walls, one of the best-preserved fortified villages in Tuscany.
Explore San Gimignano, the UNESCO-listed town of medieval towers rising above the Tuscan skyline.
Wine tasting at a rustic Chianti estate with olive oil sampling and homemade snacks included.
Scenic coach journey through the Chianti hills with commentary from your guide throughout the day.
Free time in both San Gimignano and Siena for independent exploration of shops, viewpoints, and local streets.
Itinerary
1
Departure from Florence and Drive to Monteriggioni
Meet your guide at Piazzale Montelungo Bus Terminal, a short walk from Santa Maria Novella train station. Board the coach and enjoy approximately one hour of scenic driving through the Chianti hills, with your guide providing commentary along the way.
2
Monteriggioni: The Fortified Village
Arrive at Monteriggioni and spend one hour exploring this remarkably well-preserved medieval village, entirely enclosed within its original 13th-century walls. Stroll the cobblestone lanes, enjoy a coffee at a local bar, and take in the quiet atmosphere of a town that feels largely unchanged from its medieval origins.
3
Siena: Guided Walking Tour and Free Time
A thirty-minute drive brings you to Siena, where a local professional guide leads an included walking tour of approximately one hour. The route covers Piazza del Campo, Palazzo Pubblico with its Torre del Mangia, and concludes at the Duomo, one of the finest examples of Italian Gothic architecture. Free time follows for independent exploration.
4
San Gimignano: The Town of Towers
After a one-hour drive, you arrive at San Gimignano, whose fourteen surviving medieval towers are visible from a distance as the coach approaches. Your guide leads you to a panoramic viewpoint before you pass through the ancient city gates for one hour of free exploration.
5
Chianti Wine Estate: Tasting and Producer Talk
A short drive from San Gimignano brings the group to a family wine estate in the Chianti countryside. Seated in a cellar tasting room, guests sample wines produced on the estate alongside olive oil and homemade snacks, while the producer explains the methods behind Chianti wine production.
6
Return to Florence
The coach departs the wine estate for Florence, arriving in the early evening after approximately one hour of driving. The return journey offers a final view of the Tuscan hills as the light changes at the end of the day.
What Is Included
Included
Air-conditioned coach transportation throughout the day
Professional English-speaking guide for the full tour
Local guided walking tour of Siena with a professional city guide
Wine tasting at a Chianti estate with homemade snacks and olive oil sampling
Entrance to Monteriggioni village
All taxes and service fees
Not Included
Entrance to Siena Cathedral (payable on site)
Entrance to any optional monuments in San Gimignano
Meals and personal beverages outside the wine tasting
Gratuities for guides (optional and at your discretion)
Hotel pickup and drop-off
Important Information
Please arrive at the meeting point at least 10 minutes before departure. The tour involves walking on uneven cobblestone surfaces across all four destinations.
Duration
10 hours and 30 minutes total. The tour returns to Florence in the early evening.
Meeting Point
Piazzale Montelungo Bus Terminal, Florence. Located 5 to 10 minutes on foot from Santa Maria Novella train station.
What to Bring
Comfortable walking shoes suitable for cobblestone streets, sun protection, a light layer for the wine cellar, and a valid ID.
Cancellation
Please refer to the booking confirmation for the applicable cancellation and refund policy for this tour.
Accessibility
The tour involves walking on uneven cobblestone terrain across all stops. It is rated moderate difficulty and may not be suitable for guests with limited mobility.
Age Range
The tour is suitable for most ages. Children must be accompanied by an adult. The wine tasting is reserved for guests of legal drinking age.
Book Your Tuscan Day Tour
Secure your place on this full-day journey through the medieval towns and vineyards of Tuscany, departing daily from Florence.
The tour departs from Piazzale Montelungo Bus Terminal in Florence, which is approximately 5 to 10 minutes on foot from Santa Maria Novella train station. Hotel pickup is not included.
Is the Siena Cathedral entrance fee included?▼
No, the entrance fee to Siena Cathedral is not included in the tour price. Guests who wish to enter may purchase a ticket on site during their free time after the walking tour.
What is included in the wine tasting?▼
The wine tasting at the Chianti estate includes a selection of wines produced on the property, accompanied by olive oil sampling and homemade snacks. The estate producer presents information about local winemaking during the session.
How much walking is involved in this tour?▼
The tour is rated moderate difficulty and includes walking on cobblestone streets in Monteriggioni, Siena, and San Gimignano. Comfortable, sturdy footwear is strongly recommended.
Is San Gimignano a UNESCO World Heritage Site?▼
Yes, the historic centre of San Gimignano has been listed as a UNESCO World Heritage Site. The town is particularly noted for its fourteen surviving medieval towers and the local Vernaccia white wine.
Can I purchase wine at the end of the tasting?▼
Yes, guests have the opportunity to purchase bottles of wine directly from the estate at the end of the tasting session.
Tuscany Day TourFlorence ExcursionSiena Walking TourSan GimignanoMonteriggioniChianti Wine TastingMedieval TuscanyUNESCO World HeritageItalian Gothic ArchitectureTuscan CountrysideWine Estate VisitGroup Tour Italy
This tour operates from Florence, the capital of Tuscany in central Italy, and covers four distinct destinations within the Siena province and the broader Chianti wine region. Monteriggioni is a small fortified commune in the Province of Siena, approximately 15 kilometers north of Siena itself. Siena is a historic city in central Tuscany renowned for its medieval urban fabric, listed as a UNESCO World Heritage Site. San Gimignano, located in the Province of Siena, is a small hilltop town recognized by UNESCO for its preserved medieval towers and the native Vernaccia di San Gimignano white wine. The Chianti Classico wine region stretches between Florence and Siena and is one of Italy's most recognized wine-producing zones. The entire tour route travels through landscapes representative of the Sienese hills and the broader Chianti countryside.
Region: Tuscany, Italy | Departure City: Florence | Key Destinations: Siena, San Gimignano, Monteriggioni, Chianti | Tour Type: Full-Day Cultural and Wine Tour | UNESCO Sites: Siena Historic Centre, San Gimignano Historic Centre | Difficulty: Moderate | Tour Format: Small Group Guided
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