Tours/Arezzo/Private Tour Siena San Gimignano and Chianti from Cortona
Viator · Private tour

Private Tour Siena San Gimignano and Chianti from Cortona

5.0(5)Arezzo1 hour
TRIPADVISOR5.0(5)

Description

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.

Tour Options

Private Tour Siena San Gimignano and Chianti from Cortona
  • Pickup included

Itinerary

Admission included25 min

Piazza del Campo (or simply Il Campo) is the main square of Siena. Famous for its unique shell shape, it is known worldwide for its beauty and well-preserved architecture. It is also the site of the Palio di Siena, a horse race held twice a year. By ancient tradition, the square and the Palazzo Pubblico do not belong to any contrada.

Admission not included20 min

The Siena Cathedral, or Cattedrale di Santa Maria Assunta, is one of the masterpieces of Italian Gothic architecture. Located in the heart of the city, it stands out for its extraordinary façade of white, dark green, and red marble, as well as its interior rich in artworks. It is undoubtedly one of the most beautiful and most visited cathedrals in Italy.

Pass by

Monteriggioni is a small medieval village in Tuscany, in the province of Siena. It is famous for its spectacular walls, making it one of the best-preserved fortified villages in Italy.

50 min

San Gimignano is a charming medieval village located in Tuscany, in the province of Siena. It is famous for its medieval towers, which have earned it the nickname "Manhattan of the Middle Ages". The medieval towers: There were once over 70, today 14 remain, making the village unique in the word. They were symbols of power of the noble families. UNESCO Heritage: The historic center of San Gimignano was declared a World Heritage Site by UNESCO in 1990. San Gimignano is an unmissable destination for those visiting Tuscany, perfect for immersing yourself in the medieval atmosphere and enjoying breathtaking views.

Highlights

Private transportation
WiFi on board
Bottled water
All Fees and Taxes
Air-conditioned vehicle
lunch in a family winery tour and tasting

What's included

Included
Private transportation
WiFi on board
Bottled water
All Fees and Taxes
Air-conditioned vehicle
lunch in a family winery tour and tasting

Pickup Locations & Times

We can pick up guests at any location

Traveller Ratings

5.0
5 reviews
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Important Information

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Suitable for all physical fitness levels

Reviews(5)

Q
Q106XQannab
June 20, 2026
One of the best days of my life

This was seriously the most amazing experience of my entire life Max was the funnest, funniest and coolest guide. He was so knowledgeable, so attentive so caring and so positive. I will use this company 1 million times. I had the best day ever.

K
katrinam963
September 3, 2025
From Texas to Tuscany

Max was great and helped us so much to navigate through with precise directions and enough time to enjoy a few different cities. He was such a great guide for our first time in Italy Would recommend this full day adventure to anyone wanting to leave Cortona for the day. Katrina, Meagan & Debbie *Texas*

Operator response

Hello Katrina, Meagan and Debbie, thank you so much for your lovely words! It was such a pleasure to share the day with you, and I really hope we can meet again to enjoy more of Tuscany together. Big hugs to all of you from Cortona! Massimo e Luca

H
H8704GOlukem
June 12, 2025
Wonderful trip and service!

Amazing trip with Luca. Made the trip memorable for our family of 4 and still managed to fit in a bit of time a local winery! Loved both San Gimignano and Monteriggioni and really enjoyed Luca’s knowledge of the area. Would certainly recommend Luca and would have booked for a subsequent trip but he was booked up!

A
Angela T
June 8, 2025
Luca – The Heart and Soul of Italian Travel

Luca provided outstanding customer service throughout the entire tour. He was patient professional and explained contextualized historical information so that we understood the importance of what we were experiencing. He was kind personable and flexible. He went beyond his call of duty for the tour to make sure we saw everything. He was exceptional. I would highly recommend him for any tour.

R
Relax07047001183
June 4, 2025
Wonderful experience!

Luka was wonderful! The time allocation accross each of the three places was exactly right. It was entertaining and also relaxing. We didn’t feel rushed or overwhelmed and had time to explore. I highly recommend!

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