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Voyzo
Florence

Private Day Trip: Siena, Monteriggioni, San Gimignano and Fonterutoli

Two medieval towns and a walled fortress village, plus real Chianti wine.

Private tour — just your group 8-9 hours Up to 25 guests Free itinerary changes Local expert guide
Free, no-obligation quote
  • Real pricing usually follows within a few hours
  • Private — your group only
  • Free itinerary changes
Get your price

Overview

A private day trip reaching Siena, the walled village of Monteriggioni, San Gimignano, and Fonterutoli's Chianti wine estate.

Leave the navigating to your driver so you can take photos on the scenic ride, visiting the medieval cities of Siena and San Gimignano plus the fortified village of Monteriggioni, and trying wine in the famous Chianti region at Fonterutoli.

Highlights

  • Monteriggioni's walls A real, still-intact fortified medieval village, rarely covered by other tours.
  • Fonterutoli wine estate A named, real Chianti wine estate for tasting.

What Stops Does This Tour Make?

A popular starting point — every Voyzo itinerary is fully customizable, so we'll shape the order and stops around your group.

P

Pickup

Hotel pickup included in Florence.

1

Monteriggioni's walls

A real, still-intact fortified medieval village, rarely covered by other tours.

2

Fonterutoli wine estate

A named, real Chianti wine estate for tasting.

D

Drop-off

Back to your hotel, home, or the airport — whenever your day wraps up.

What's Included

A private vehicle and driver, just for your group
A professional, knowledgeable local guide
Door-to-door pickup and drop-off
A fully customizable itinerary built around you
All tolls, parking, and fuel

What's Not Included

Attraction admission tickets, unless noted as included
Meals and snacks
Gratuities for your guide or driver
Personal expenses

Why Book a Private Tour With Voyzo?

Your group only — never combined with strangers
Crowded 50+ seat group buses
Fully custom stops, built around you
A fixed script with no flexibility
Door-to-door pickup, wherever you're staying
Meeting at a fixed public meeting point
Direct, transparent pricing — no marketplace markup
Third-party booking fees

Important Information

Know Before You Book

  • Group size can range from 1 to 25 guests — we match the vehicle to your party.
  • Pricing depends on group size, vehicle, and tour length, and is confirmed after your quote request.
  • Tour duration is flexible — the times shown are a typical starting point.

Know Before You Go

  • We'll confirm your exact pickup time and vehicle details after booking.
  • Bring a camera, comfortable shoes, and weather-appropriate layers.
  • Your pickup address is required to finalize the itinerary.

Special Requests

  • Mobility needs, dietary notes, or accessibility requirements? Let us know when requesting your quote and we'll arrange accordingly.
  • Traveling with young children or larger groups — just tell us, and we'll recommend the right vehicle.

Frequently Asked Questions

It's one of Tuscany's best-preserved medieval walled villages, with its ring of towers still standing.
It's a medieval legend, not documented history. The black rooster itself is real as a symbol — it dates to the 14th-century Lega del Chianti and is still used by the modern Chianti Classico Consortium — but the folk tale of a rigged rooster race deciding the Siena-Florence border is a popular story, not a verified historical event.
Once your quote is accepted, we'll confirm your exact pickup time, vehicle, and driver details by email ahead of your tour date.
Yes — reach out to our team any time before your tour and we'll do our best to accommodate itinerary or schedule changes.

About This Tour

A private day trip reaching Siena, the walled village of Monteriggioni, San Gimignano, and Fonterutoli's Chianti wine estate. Leave the navigating to your driver so you can take photos on the scenic ride, visiting the medieval cities of Siena and San Gimignano plus the fortified village of Monteriggioni, and trying wine in the famous Chianti region at Fonterutoli.

Monteriggioni was built to be a problem for Florence. The Sienese raised its walls between 1213 and 1219 on a hilltop overlooking the old Via Cassia, and the fortress town — 14 towers on square bases, still standing largely untouched since construction — fell only once in its history, in 1554, and only through betrayal rather than a direct assault. Dante was so struck by it during his exile that he compared the towers to giants guarding the pit of Hell in Canto XXXI of his Inferno.

Fonterutoli, your wine stop, has belonged to the Mazzei family since 1435 — 24 generations in the same hands — though the family's ties to this exact wine run deeper still. In 1398, ancestor Ser Lapo Mazzei wrote one of the earliest documents ever to use the term "Chianti wine," and the estate itself sits on ground that holds an Etruscan necropolis and an old Roman road beneath its vineyards.

Fonterutoli also happens to be the setting of Chianti's best-known legend. The story goes that Siena and Florence once settled a border dispute by each sending a knight out at dawn toward the other — Florence rigged the contest by starving its chosen rooster so it would crow (and free the knight) well before sunrise, letting the Florentine rider claim ground as far out as Fonterutoli, just 12 km from Siena itself, before the two met. It's a medieval tale rather than verified history, but it's the reason Chianti wine still carries a black rooster on the label today.

Not quite what you're looking for?

Every Voyzo tour is a starting point — tell us what you have in mind and we'll build it.

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