Italy · Wine & Beer

8-Hour Siena and Chianti Wine Tour from Florence with San Gimignano

8 Hours Round trip from Florence Easy pace

The journey

Trip highlights
  • 01 Admire the beautiful Florentine hills on the drive through the Tuscany countryside
  • 02 Explore the Chianti wine area and the historic fortress of Monteriggioni
  • 03 Visit Piazza del Campo and see Siena's Cathedral, Baptistery, and bell tower
  • 04 Enjoy a traditional Tuscany lunch and wine tasting at an organic winery in San Gimignano
  • 05 Climb Torre Grossa in San Gimignano and taste delicious gelato at Antica Gelateria di Piazza
  • 06 Take in a stunning panoramic view of Florence from Piazzale Michelangelo

Enjoy a wonderful day in Tuscany on a tour from Florence to Siena, Chianti, Monteriggioni, and San Gimignano. Admire the beautiful Florentine hills and explore the Chianti and Siena wine areas as you visit landmarks such as Piazza del Campo, the Cathedral, the Baptistery, and the bell tower. In San Gimignano, stop at an organic winery for a traditional Tuscany lunch and wine tasting before continuing through vineyards and olive groves. Complete the experience with delicious gelato at Antica Gelateria di Piazza and a stunning panoramic view of Florence from Piazzale Michelangelo.

Climb the Torre Grossa and taste the delicious gelato at Antica Gelateria di Piazza.

From the itinerary

At a glance

What this trip includes

Duration 8 Hours
Tour type Private
Activity level Easy
Accommodation Not included
Transport Included
Wheelchair access Not applicable
Cities Florence, Siena, Montalcino, Chianti, San Gimignano
Languages English, Italian

Day by day

The itinerary

1
Day 01

Siena, Monteriggioni, San Gimignano, and Chianti from Florence

09.00 AM: Departure from Florence or its vicinity.

  • 10.15 AM: Approaching Siena through the beautiful Tuscany countryside, admire the beautiful Florentine hills. You will be guided through the Chianti wine area. Then, go up the hills of Chianti and arrive in Siena. Visit Piazza del Campo and see the Cathedral, the Baptistery, and the bell tower.

  • 12.30 AM: Depart from Siena to the Chianti wine region and Monteriggioni. Until the 11th century, Monteriggioni was a stopping station on the Francigena Road in Tuscany. Siena transformed Monteriggioni into the imposing fortress that it is today to protect its northern boundary from being breached by its then-enemy, Florence. Walk on the defensive walls and admire the Chianti region.

  • 01.00 PM: Arrive in San Gimignano and visit an organic winery for a typical Tuscany lunch and a wine tasting session. Some of the wines and virgin oils tasted here are Vernaccia white wine, Chianti Classico, Chianti Riserva, Brunello from Montalcino, Supertuscan, extra virgin olive oil, truffle oil, and Vinsanto with Cantuccini.

  • After lunch and the wine tasting, drive along the Tuscany hills and see the different vineyards and olive groves.

  • 02.00 PM: Tour some of the 14 towers of San Gimignano, the 14 remaining out of the original 72 erected in the 13th century. Climb the Torre Grossa and taste the delicious gelato at Antica Gelateria di Piazza.

  • 04.30 PM: Return to Florence, but only after making a stop at Piazzale Michelangelo for a stunning panoramic view of the city.

  • 05.00/05.30 PM: End of the tour, with drop-off at your accommodation in Florence.

Chianti vineyards, San Gimignano towers, Piazzale Michelangelo

Where this trip takes you

Chianti vineyards, San Gimignano towers, Piazzale Michelangelo

The route

Where you'll travel

Tour route map
Round trip from Florence 5 cities · 8 Hours

The fine print

Trip details

What's Included

  • Services of a Tuscany tour guide

  • All-inclusive tour pricing since 1990

  • Pick-up and drop-off from your accommodation

  • Lunch and wine tasting at an organic farm in Chianti

  • Panoramic stops in Chianti

  • Photography stop at Michelangelo Square

What's Not Included

  • Entrance tickets for the museums and Duomo

Logistics

Meeting & route

Meeting point
Florence, Metropolitan City of Florence, Italy
Tour start
Florence, Metropolitan City of Florence, Italy
Tour ends at the same location as the start point.
End of the journey

Your 8 hours finish where they began, in Florence.

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