Private Tuscany day trip from Florence:
Siena, Chianti, and San Gimignano
Destination
Florence, Italy
Duration
9 hours
Tour size
Max 6
Language
English
Overview
Step into medieval Siena, sit down to a long lunch at a Chianti vineyard, and spend an afternoon among San Gimignano's towers, all in a single day with every detail handled for you. This private Tuscany day trip from Florence covers Siena, Chianti, and San Gimignano without a single bus timetable.
- •Trace the shell-shaped curve of Siena's Piazza del Campo, where the Palio horse race has drawn crowds since the 1600s
- •Sit down to a homemade Tuscan lunch at a family-run Chianti vineyard, with wine from the vines just outside the door
- •Taste Chianti Classico varietals while the winemakers walk you through their cellars and vines
- •Roam San Gimignano's cobblestone streets beneath its fourteen surviving medieval towers
- •Watch the Tuscan countryside shift from city walls to vineyard rows to hilltop silhouettes between every stop
What's included
- Private English-speaking driver for the full day
- Local guide in Siena
- Wine tasting at a family-run Chianti vineyard
- Farm-to-table Tuscan lunch with wine
- Air-conditioned private transport
- Free time in San Gimignano
You will visit
- Piazza del Campo, Siena
- Siena Cathedral (exterior)
- Siena's historic Contrade neighborhoods
- A family-run Chianti vineyard and cellars
- Tuscan farm-to-table lunch
- San Gimignano's medieval towers and hilltop streets
- Tuscan countryside views between stops
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What to expect
Siena on foot, where seventeen neighborhoods still compete
Siena still looks the way it did when the Black Death froze its growth in 1348. A local guide walks you through the heart of the city, from the Piazza del Campo where the Palio horse race has been run since the 1600s to the striped marble exterior of Siena's cathedral. You'll hear how the city's seventeen Contrade districts still celebrate, compete, and feud as they have for centuries.
Chianti cellars and a long Tuscan lunch
After Siena, your driver takes you into the Chianti hills to a family-run vineyard. You'll tour the cellars and vines with the winemakers, tasting Chianti Classico and hearing how the soil and altitude shape each vintage. Then you sit down to a homemade Tuscan lunch prepared with ingredients from the estate, paired with the vineyard's own wines. The bread is still warm and the olive oil was pressed from the trees outside the window.
"People still live in their Contrada, still race the Palio, still argue about who won in 1982. That's what I show visitors."
Cristina,
WalksDevour local guide in Siena
"When we open the cellar doors and the cold air hits you, that's when people stop thinking about the next stop. They're just here."
Lorenzo,
WalksDevour guide
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Frequently asked questions
Our guides love answering your questions. Here are some things they'd like you to know before you arrive.
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