Italy · Wine & Beer

Private Tour Of Chianti with Wine Tastings

8 Hours Round trip from Pickup service provided in Florence. Easy pace

The journey

Trip highlights
  • 01 Private full-day tour through Tuscany and the Chianti hills
  • 02 Visit Monteriggioni, Siena, San Gimignano, Chianti, and Pisa
  • 03 Enjoy wine tastings, local snacks, and fresh olive oil at a winery
  • 04 See Piazza del Campo, Torre del Mangia, and Siena Cathedral
  • 05 Explore the UNESCO-listed town of San Gimignano
  • 06 Admire Pisa’s Piazza dei Miracoli and the Leaning Tower
  • 07 Travel in a private Mercedes car or minivan with hotel pickup and drop-off

Discover the best of Tuscany on a private full-day journey through Chianti and some of the region’s most iconic historic towns. Travel through rolling hills and vineyard landscapes as you explore medieval Monteriggioni, elegant Siena, and hilltop San Gimignano before continuing to the heart of Chianti for a winery visit and tastings.

Along the way, admire celebrated landmarks including Piazza del Campo, Siena Cathedral, and the towers of San Gimignano, with time to enjoy each stop at your own pace. The day also includes a visit to Pisa’s Piazza dei Miracoli to see the Baptistery, Cathedral, and the famous Leaning Tower, combining Tuscan scenery, architecture, local flavours, and wine into one memorable experience.

After learning the secrets of the Chianti wine production process from the expert owner of the wine estate, indulge in a tasting of the high quality wines, local snacks, and fresh olive oils.

From the itinerary

At a glance

What this trip includes

Duration 8 Hours
Tour type Private
Activity level Easy
Accommodation Included
Transport Included
Wheelchair access No
Cities Florence, Pisa, Siena, Chianti, San Gimignano
Languages English, German, Italian, Spanish

Day by day

The itinerary

1
Day 01

Crossing over the beautiful Chianti hills, you will first arrive at the medieval, hilltop gem of MONTERIGGIONI, with its ancient walls still perfectly intact. As you stroll through the rustic streets, you will feel as though you are traveling through time into the Renaissance era. Enjoy a more modern espresso or cappuccino before heading to your next destination!Your tour will continue to the symbolic town of SIENA, famous for its splendid examples of Gothic architecture and its Palio horse race, an annual tradition.Follow your local guide to the intriguing Piazza del Campo, where the magnificent Palazzo Pubblico and Torre del Mangia stand.Next, head to Piazza del Duomo and admire the imposing Cathedral, one of the finest achievements of Italian Gothic architecture. Before leaving Siena, enjoy some free time to exlplore its historic centre at your leisure.Next, you will head to SAN GIMIGNANO, famous for its white wine - the world renowned Vernaccia, and its skyscrapers, declared a World heritage Site by UNESCO! Enjoy some free time for independent sightseeing, strolling around the narrow streets, and admiring the beautiful, panoramic landscapes from the hilltop viewpoints.Finally, you will spend some time in the heart of CHIANTI, with its picture-perfect landscapes. After learning the secrets of the Chianti wine production process from the expert owner of the wine estate, indulge in a tasting of the high quality wines, local snacks, and fresh olive oils. Salute!Then, following the panoramic roads of the Chianti region, we will get to Pisa and its stunning Piazza dei Miracoli, where you will admire the Baptistery, the Cathedral and, of course, the famous Leaning Tower.We will return to Florence filled with memories of a marvelous day in the history and beauty of Tuscany.

The route

Where you'll travel

Tour route map
Round trip from Pickup service provided in Florence. 5 cities · 8 Hours

The fine print

Trip details

What's Included

  • Pick up and drop off at your hotel
  • Private Mercedes car or minivan
  • Free time in Siena, San Gimignano and the Chianti wine region
  • WiFi on board
  • Delicious lunch from a local provider
  • Tour of a marvelous winery, plus generous wine tastings!
  • Professional guided tour of Siena (Optional)
  • Siena Cathedral Entrance Ticket with priority access (Optional)

Know before you go

  • PUBLIC TRANSPORTATION NEARBY
  • Not wheelchair accessible
  • Not stroller accessible
  • Not suitable for pets
  • Infants must not sit on laps
  • Infant seats unavailable
  • Comfortable shoes are recommended
  • please send us a message in order to notify us of your accommodation in town.
  • Meeting Point from your accommodation.

Logistics

Meeting & route

Meeting point
Pickup service provided in Florence.
Tour start
Pickup service provided in Florence.
Tour ends at the same location as the start point.
End of the journey

Your 8 hours finish where they began, in Pickup service provided in Florence..

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