FULL DAY TOUR
From Florence: Siena & San Gimignano Day Tour
Truffles, Towers & Timeless Tuscany — Light Lunch & Wine Tasting
FROM
€290 PP
Discover Tuscany Through Siena, San Gimignano & Wine
An 8-hour private tour from Florence combining the medieval grandeur of Siena and the iconic skyline of San Gimignano, with a light gourmet lunch and wine tasting at a selected estate in the Chianti Colli Senesi hills. History, landscape, flavour and authentic Tuscan life — all in one extraordinary day.
8h
Duration
2 Pax
Minimum
€290
Starting
5 Star
Rating
Why You Should Choose This Tour?
- A perfectly curated full-day itinerary from Florence combining two of Tuscany’s most beloved medieval destinations.
- Explore Siena’s Piazza del Campo and Duomo with an expert guide — one of the most beautiful cities in Italy.
- Discover the story of Siena’s ancient rivalry with Florence and the living traditions of the Contrade.
- Enjoy a light gourmet lunch with wine tasting at a carefully selected estate in the Chianti Colli Senesi hills.
- Experience San Gimignano’s famous medieval towers, truffle culture and charming historic centre.
- Taste Vernaccia di San Gimignano — the area’s celebrated white wine — on a panoramic terrace or historic tower.
- Private van for small groups — comfortable, flexible and entirely personalised.
- Perfect for American travelers and first-time visitors to Tuscany who want the best of the region in a single day.
- Expert local guide throughout — storytelling that connects art, history, food and people.
What Does This Tour Include?
-
Included
- Private van with dedicated driver for the entire day
- Expert local English-speaking guide
- Guided walk through Siena: Piazza del Campo, Piazza del Duomo and historic centre
- Guided visit and light lunch at a selected Chianti Colli Senesi estate with wine tasting
- Guided walk through San Gimignano with storytelling on towers, truffle culture and medieval history
- Glass of Vernaccia di San Gimignano on a panoramic terrace or historic tower
- Pick-up and drop-off from Florence city centre
- Tour insurance
-
Not Included
Just few spots available
Itinerary
Pick-up from Florence
Morning departure from your accommodation or agreed meeting point with a private van and dedicated driver.
Scenic Stop: Piazzale Michelangelo
Enjoy a panoramic view over Florence and an introduction to the history of Tuscany and the Florence–Siena rivalry.
Stop 1: Siena
Guided walk through the historic centre, including Piazza del Campo and Piazza del Duomo. Learn about the Palio, medieval politics, and the city’s unique identity. Free time to explore.
Stop 2: Chianti Colli Senesi (Wine Estate)
Visit a selected estate in the Chianti hills. Enjoy a light gourmet lunch with wine tasting, featuring local wines and traditional Tuscan products.
Stop 3: San Gimignano
Discover the famous “Medieval Manhattan” with its iconic towers. Walk through the historic centre and learn about its history, rival families, and truffle culture.
Final Experience: Vernaccia Wine Tasting
Enjoy a glass of Vernaccia di San Gimignano on a panoramic terrace or inside a historic tower.
Return to Florence
Relax on the scenic drive back, arriving in Florence in the early evening.
Highlights
- Piazza del Campo in Siena — one of the most beautiful medieval piazzas in the world and stage of the legendary Palio.
- The Siena Duomo — a Gothic masterpiece of extraordinary richness and visual complexity.
- The story of Florence vs. Siena — the greatest rivalry in Tuscan history, told from the Sienese perspective.
- Light gourmet lunch and wine tasting at a selected Chianti Colli Senesi estate.
- San Gimignano’s medieval towers — 14 surviving towers from an original 72, the most dramatic skyline in Tuscany.
- Truffle culture in San Gimignano — the white and black truffles of the San Gimignano hills, a local treasure.
- Vernaccia di San Gimignano — Italy’s first ever DOC white wine, enjoyed on a panoramic terrace.
- A complete Tuscan day that blends history, art, food and landscape in perfect balance.
Medieval cities, rolling vineyards, and authentic Tuscan flavours — experience Siena, San Gimignano, and Chianti in one unforgettable day.
Know Before You Go.
- Total Duration: approximately 8 hours (full day)
- Tour Type: Private full-day tour by van with guided stops
- Tour Level: Easy to moderate — walking on cobblestone streets, some inclines in both Siena and San Gimignano
- Private van with dedicated driver included for the entire day.
- Light gourmet lunch and wine tasting at the estate are included.
- Minimum age for alcohol tasting: 18 years old
- Languages available: English, Italian
- Please be ready at the agreed pick-up point at the confirmed departure time
- Comfortable, layered clothing and sturdy walking shoes are recommended.
- Siena and San Gimignano are hilly towns — a moderate level of fitness is helpful.
- Entrance tickets to the Siena Duomo and San Gimignano towers are not included but can be arranged upon request.
Frequently Asked Questions
Pick-up is from Florence city centre. The exact pick-up address is confirmed upon booking.
Yes. A light gourmet lunch is included at a selected wine estate in the Chianti Colli Senesi, accompanied by a guided wine tasting.
At the Chianti estate you will taste the estate’s own wines, typically including a Chianti Colli Senesi. In San Gimignano, the experience concludes with a glass of Vernaccia di San Gimignano, the area’s celebrated white wine.
The Palio takes place twice a year (2 July and 16 August) and requires separate ticketing. However, your guide will bring the history and emotion of the Palio to life through storytelling, and you will visit Piazza del Campo where the race takes place.
San Gimignano is known as the ‘Medieval Manhattan’ for its 14 surviving medieval towers. Originally there were 72, built by wealthy rival families as symbols of power and prestige. Today they define one of the most recognisable skylines in Italy.
Yes. San Gimignano has excellent local shops where you can purchase truffles, truffle products, Vernaccia wine and other local specialities. Your guide can recommend the best producers.
This tour is ideal for first-time visitors. It combines two of the most iconic Tuscan destinations with authentic gastronomic and cultural experiences, offering a comprehensive and memorable introduction to the region.
Yes, booking in advance is essential to coordinate the private van, the estate reservation and the guide.
The interior of the Siena Cathedral (Duomo di Siena) is not accessible during religious services, which typically take place on Sunday mornings. If your tour falls on a Sunday, the exterior visit and the storytelling in Piazza del Duomo are fully included; the guide will adjust the programme accordingly and may suggest visiting the Cathedral exterior, the Baptistery or the panoramic viewpoints instead. We always confirm this detail in your pre-tour information.
Both Siena and San Gimignano are medieval hilltop towns built on steep terrain, with cobblestone streets and steps throughout. The tour involves a moderate amount of walking on uneven surfaces and some inclines. It is not suitable for guests using wheelchairs or with significant mobility difficulties. If you have specific concerns, please contact us before booking and we will advise on the best options for your group.
Coach tours to Siena and San Gimignano typically carry 40–55 passengers, follow a fixed rapid schedule and use multi-language simultaneous commentary. Our tour uses a private van for small groups, with a dedicated guide speaking exclusively in English, flexible timing adapted to your group’s pace, a personally selected wine estate for lunch, and access to a panoramic terrace in San Gimignano that larger groups cannot reach. The quality of the experience — and the depth of the human connection — is simply not comparable.
Vernaccia di San Gimignano is a dry white wine produced exclusively from the Vernaccia grape in the hills around San Gimignano. It holds the distinction of being the first wine in Italy to receive DOC status, in 1966, and was later upgraded to DOCG. Characterised by its pale golden colour, fresh acidity and almond-tinged finish, it pairs beautifully with the local cuisine and is best enjoyed chilled with a view of the town’s famous towers — exactly as your tour concludes.
For this private full-day tour, we require cancellations to be made at least 7 days before the departure date for a full refund. Cancellations within 7 days of departure are subject to a full penalty, as the private van, wine estate and guide are all reserved exclusively for your group. For bookings made within 7 days of the tour date, the full amount applies from the moment of booking. Please contact us immediately if your plans change and we will do our utmost to assist.
What They Say About Us
From the twilight shadows to the final wine glass, our guests have walked the path of Renaissance secrets. See why they fell in love with Florence’s most provocative side.
Booked the Uffizi tour for our anniversary. We went in knowing nothing and came out understanding everything. Worth every euro and then some.
Sarah L
The Val d’Orcia full-day tour felt like a dream. Eight hours of pure Tuscany. Marco’s team is exceptional. This is how travel should feel slow, beautiful, meaningful.
David K.
The Artisans tour was the highlight of our entire trip. Seeing real craftsmen at work in those Oltrarno workshops nothing compares. Highly recommend.
Robert & Claire T
An absolutely extraordinary evening. Our guide knew stories about Florence I’ve never read in any book. The wine tasting at the end was perfect. We’ll be back.
Jennifer M
Join Our Community of Florence Lovers
From the twilight shadows to the final wine glass, our guests have walked the path of Renaissance secrets. See why they fell in love with Florence’s most provocative side.
Born and raised in Tuscany, we offer iconic experiences through high-quality guided led excursions.
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