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Tuscany Grand Tour from Florence: Pisa, Chianti and Siena

Tuscany Grand Tour from Florence: Pisa, Chianti and Siena

5.0(5 reviews)
11 hour(s)
English
Skip the line
Florence, Italy

Explore Pisa and capture the beauty of the Leaning Tower and Piazza dei Miracoli

Enjoy a wine tour and tasting in the heart of the Chianti Classico region

Savor a traditional Tuscan lunch with local products and fine wines

Discover Siena’s medieval charm and iconic landmarks

Visit Monteriggioni Castle for a perfect panoramic photo stop

Price start from

371

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Begin your journey from Florence with a delightful drive through the rolling hills and scenic landscapes of the Tuscan countryside. The day unfolds with a visit to the historic city of Pisa, a treasure of Italian heritage. Stroll through the enchanting Piazza dei Miracoli, where the majestic Duomo and the beautifully designed Battistero stand as timeless symbols of artistry and devotion. Capture the moment with the world-famous Leaning Tower, a marvel that continues to inspire travelers from around the world. As you take in the atmosphere of this remarkable city, you will feel the essence of Tuscany in every view and detail.

Continue your adventure into the heart of the Chianti Classico region, where the beauty of vineyards and olive groves creates a picture-perfect scene. Here, a warm welcome awaits you at a traditional estate, where a local wine producer will introduce you to the art and passion behind Tuscany’s celebrated wines. Savor a guided wine tasting, paired with a rustic and delicious Tuscan lunch prepared with local ingredients and traditional recipes. The journey then leads you to the medieval charm of Siena, where narrow streets, stunning cathedrals, and the famous Piazza del Campo tell tales of history and culture. Before returning to Florence, you will pause at the enchanting Monteriggioni Castle, a perfect finale to a day filled with discovery, flavors, and breathtaking views that truly embody the spirit of Tuscany.

Professional local guide

Comfortable transportation from and to Florence

Wine tasting and estate visit

Traditional Tuscan lunch

Guided tour in Siena

Personal expenses

Hotel pickup and drop-off

Gratuities

Comfortable clothes and shoes

Water bottle

Camera

Travelers with Limited mobility impairments
Families with children
Groups of friends
Physically fit travelers
Seniors and mature travelers
Photography lovers

Not wheelchair accessible

This tour will have a maximum of eight travelers

Confirmation will be received at time of booking

Confirmation will be received at time of booking

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Activity Provider: Keys of Italy

Customer Reviews

5 reviews
5.0
based on 5 reviews
J

Jennifer

October 12, 2025
Google

Filippo was our tour guide through 3 amazing boutique wineries. Incredibly knowledgeable and gracious, he made the tour a genuine and delightful experience. At each winery not only did we taste delicious wine and food, but it felt like we were visiting the homes of friends. The winery owners were all passionate about their wines and took great care with every step of the process. Wonderful authentic, intimate experience I would recommend highly. Just a magical day!

N

Nathan

October 05, 2025
Google

Angie did a wonderful job showing us the Chianti region while keeping the tour fun and entertaining. The 3 wineries visited all were unique and great in their own way. We had personal tours from the owners of 2 of the wineries which was very cool to learn their stories. The small group setting (8 people or less) was perfect size and being picked up from downtown Florence made the whole experience super easy. 10/10 would recommend!

H

Hannah

October 04, 2025
Google

I cannot say enough amazing things about this tour! Each winery had its own unique history and story behind each of the wines we tasted, the lunch La Pia was delightful, and the views were gorgeous. An absolute must have if you're looking for a unique intimate Tuscan experience beyond the hustle and bustle of Florence. The highlight of the tour was our guide, Filippo. He was such a genuine and kind person who took so much care in giving us the best quality experience. His knowledge of the wine and region was exceptional and gave us such a greater understanding and appreciation for the wine and for Tuscany.

K

Kayla

September 07, 2025
Google

My husband and I could not have imagined a better experience! Angie was our tour guide and she was amazing! She took us to three small, family owned wineries where we learned about the wine making process. We were able to taste several wines and olive oil at each location, lunch was included at the second winery and it was one of the best meals we had! We loved that the tour size was only up to 8 people, it really made for an intimate experience. We would recommend this to anyone traveling through Florence!

V

Vegan

August 18, 2025
Google

Fabulous tour, we had an amazing time visiting local wineries, getting to hear their stories and seeing what they do in a very personalised way. Our guide was Filippo who was extremely knowledgeable about the vineyards, local area and wines in general. Filippo kept everything on track and was a lovely host. We picked this tour as it catered to vegans which most of the others don’t. They took so much care over how they planned the day out and looked after the group. An amazing experience from start to finish and would thoroughly recommend.

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Discover the wonders of Florence, Italy with this unforgettable experience. The journey then leads you to the medieval charm of Siena, where narrow streets, stunning cathedrals, and the famous Piazza del Campo tell tales of history and culture. Before returning to Florence, you will pause at the enchanting Monteriggioni Castle, a perfect finale to a day filled with discovery, f...