• Rome
  • Vatican
  • Florence
  • Venice
  • Milan
  • Pompeii
  • Barcelona
  • Madrid
  • San Sebastian
  • Seville
  • Lisbon
  • Paris
  • London
  • New York City
  • Niagara Falls (CA)
  • San Juan (Puerto Rico)
  • Colosseum
  • Vatican
  • St. Mark's Basilica & Doge's Palace
  • David & Duomo
  • Pompeii
  • Sagrada Familia
  • Prado
  • Alcazar of Seville
  • Louvre
  • Eiffel Tower
  • Versailles
  • Tower of London
  • Westminster Abbey
  • Buckingham Palace
  • Changing of the Guard
  • Grand Central Terminal
  • Met Museum
  • Statue of Liberty
  • Niagara Falls
  • Rome
  • Florence
  • Venice
  • Barcelona
  • Madrid
  • San Sebastian
  • Seville
  • Lisbon
  • Paris
  • London
  • Rome
  • Vatican
  • Venice
  • Florence
  • Milan
  • Pompeii
  • Barcelona
  • Madrid
  • San Sebastian
  • Seville
  • Lisbon
  • Paris
  • London
  • About
  • Press & media
  • Partners
  • FAQ
  • Guide with us
  • Blog
  • Careers
  • Contact

Company

  • About
  • Meet WalksDevour
  • Press & Media
  • Careers
  • Guide with us

Support

  • Manage my booking
  • FAQ
  • Cancellation policy
  • Contact

Partners

  • Travel agents
  • Affiliate program
  • Content creators

More

  • Blog
  • Walks of Italy
  • Devour Tours
PrivacyTerms & conditionsTerms of use

© 2026 Walks LLC, Millenia Park One, 4901 Vineland Road, Suite 200, Orlando, Florida 32811, USA

© 2026 Walks LLC, Millenia Park One, 4901 Vineland Road, Suite 200, Orlando, Florida 32811, USA

Privacy policyTerms & conditionsTerms of use
Home/Florence tours/Tuscany day trip from Florence: Chianti, San Gimignano, and Siena

Tuscany day trip from Florence

Chianti, San Gimignano, and Siena

From $235per person
Tuscany day trip from Florence: Chianti, San Gimignano, and Siena

Destination

Florence, Italy

Duration

9 hours

Tour size

Max 14

Language

English

Overview

Drive into the Tuscan hills for a day of medieval towers, long lunches, and the wines they were made to go with. This is the Florence to Tuscany tour that hands you San Gimignano, Chianti, and Siena with the road and the table taken care of.

  • •Watch Florence wake up from Piazzale Michelangelo before the morning crowds arrive
  • •Wander the medieval lanes of San Gimignano, a UNESCO town once crowned by seventy-two stone towers
  • •Settle into a family-run Chianti farm and winery for a homemade Tuscan lunch and five tastings of the family's best wines
  • •Step into Piazza del Campo, the shell-shaped square where Siena's bareback Palio horse race thunders twice a year
  • •Ride between stops through the cypress hills and vineyards of the Chianti countryside

What's included

  • Free time in Siena and San Gimignano's historic centers
  • Five-tasting wine flight and full lunch at a family-run Chianti winery
  • Professional English-speaking tour leader
  • Dedicated professional driver
  • Air-conditioned luxury minivan transport
  • Headsets for clear narration throughout

You will visit

  • Piazzale Michelangelo
  • San Gimignano (UNESCO World Heritage Site)
  • Family-run Chianti winery and vineyard
  • Siena, including Piazza del Campo and Siena Cathedral (exterior)
  • Tuscan countryside between Florence and Chianti
$235
per person
July 2026
MTWTFSS

Select a start time

Choose a tour date

No time slots available for this date

Select tickets & quantity

Total price

$0
  • Overview
  • What's included
  • What to expect
  • Reviews
  • FAQs

What to expect

Piazzale Michelangelo: Florence before the city is awake

Ten minutes after leaving the meeting point, you're standing above Florence at the city's best vantage point, with the Duomo, the Arno, and the Tuscan hills laid out below. At nine in the morning the square is almost empty, and the light is just reaching the dome of the Cathedral of Santa Maria del Fiore across the river. Your tour leader starts the story of the eight-hundred-year rivalry between Florence and Siena here, with the city you'll leave on one side and the road to Siena on the other.

San Gimignano: the medieval skyline that survived

The minivan takes you through the gates of the old town, inside walls that have stood for eight hundred years. San Gimignano was once a city of seventy-two stone towers, built by rival families competing for height and status. The fourteen that still stand are why UNESCO protects the skyline. Your tour leader points you toward the Duomo, the Rocca, and Gelateria Dondoli, four-time winner of the Gelato World Championship, and then the medieval streets are yours to explore on your own.

Dietary Needs: If you have dietary needs, let us know when you book. Vegetarians, pescatarians, and most allergies can be accommodated by the winery's kitchen with advance notice.

"Tuscany is too big to see in a day. So we built a day that doesn't try — one medieval town, one working farm, one cathedral square."

Chiara Santi,

WalksDevour Tuscany product designer

Postcards from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Tuscany day trip from Florence

Recent reviews & recommendations

Frequently asked questions

Our guides love answering your questions. Here are some things they'd like you to know before you arrive.

Seize every moment in Florence

Florence in a day: David, Botticelli, and Brunelleschi's dome
$169$149

Florence in a day: David, Botticelli, and Brunelleschi's dome

2704 reviews
Max. 15
Oltrarno at sunset: Florence food and wine tour
$114$110

Oltrarno at sunset: Florence food and wine tour

1197 reviews
Max. 12
VIP David & Duomo tour: Above the crowds, inside the dome
$209$195

VIP David & Duomo tour: Above the crowds, inside the dome

1588 reviews
Max. 18
Alone in the Duomo: VIP after-hours tour with Dome climb & private terrace access
$198

Alone in the Duomo: VIP after-hours tour with Dome climb & private terrace access

106 reviews
Max. 19