Florence: Tuscany Grand Tour-Siena, San Gimignano, Chianti & Pisa
Description
Get ready for the ultimate Tuscan day trip — a journey through the region’s most iconic towns, unforgettable landscapes, and world-famous flavors. Depart from Florence aboard a luxury minivan with your expert tour leader. Begin in Siena, where a guided walking tour reveals medieval alleys, Piazza del Campo, and the traditions of the Contrade. Enjoy a surprise local tasting before heading to San Gimignano, the hilltop town of towers, with free time to explore artisan shops and stunning views. Then relax with a typical Tuscan lunch before reaching Pisa. Admire the Leaning Tower, cathedral, and baptistery in the breathtaking Miracle Square. This Grand Tour is the perfect blend of art, history, wine, and countryside charm — ideal for travelers who want it all in one unforgettable day. Short on time? Choose our afternoon option, with Siena, San Gimignano, and a sunset wine tasting and Tuscan dinner in the Chianti hills — perfect for those who prefer a slower pace and golden-hour magic.
Tour Options
Itinerary
Meet your tour leader at 7:45 AM in Piazza Mentana, just outside the Towns of Italy Office. After a warm welcome, depart at 8:00 AM aboard a luxury Mercedes minivan (max 8 guests) equipped with A/C and free Wi-Fi. Get ready to relax and enjoy panoramic views of the rolling Chianti countryside, dotted with cypress-lined roads, olive groves, and historic villas. Your expert driver will introduce the day’s program as you begin your unforgettable Grand Tour of Tuscany.
Arrive in Siena and meet your local licensed guide for a captivating walking tour through one of Tuscany’s most historic cities. Discover the Basilica of San Domenico, walk along medieval alleys like Via della Sapienza and Piazza Salimbeni, and admire noble palaces along Via Banchi di Sopra. Explore Piazza Tolomei and enter the majestic Piazza del Campo, famous for the Palio horse race. Continue past the Battistero and conclude at the magnificent Duomo, all while learning about Siena’s Contrade and its proud cultural identity.
Before leaving Siena, enjoy a delightful local tasting experience curated by your guide. Savor traditional Tuscan flavors such as cantucci with Vin Santo, ricciarelli, or other seasonal specialties that reflect the rich gastronomic heritage of the region. This moment is a delicious introduction to the day’s culinary highlights and a unique opportunity to indulge your senses in the heart of medieval Tuscany.
Continue your journey through the scenic Via Cassia, passing charming hamlets like Monteriggioni and Colle Val d’Elsa, until you reach San Gimignano. Known as the “medieval Manhattan” for its soaring towers, this UNESCO World Heritage town offers breathtaking views and timeless charm. Enjoy FREE TIME to stroll through artisan boutiques, sample Vernaccia wine, admire frescoed churches, or climb Torre Grossa for a panoramic vista—it's your Tuscan postcard come to life.
Indulge in a traditional Tuscan lunch at a carefully selected trattoria or farmhouse in the Chianti area. Taste regional favorites like handmade pasta, local cured meats, seasonal vegetables, and dessert—always paired with house wines. This moment is a highlight of the day: authentic flavors served in an idyllic rural setting, perfect for relaxing and soaking in the Tuscan lifestyle before heading to your final stop.
Arrive in Pisa and enjoy free time in the iconic Piazza dei Miracoli. Admire the world-famous Leaning Tower, the Baptistery, and the Cathedral in one of Italy’s most impressive monumental complexes. Although tickets for climbing the tower are not included, you may purchase them on-site if time permits. Capture your perfect Pisa photo before boarding the minivan for the final leg of your journey. Return to Florence by 7:30 PM, full of memories from a day rich in art, history, flavors, and unforgettable views.
Highlights
What's included
Traveller Ratings
Important Information
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Minimum drinking age is 18 years
- Please advise any specific dietary requirements at time of booking
- Short on time? Choose our AFTERNOON OPTION, with Siena, San Gimignano, and a sunset wine tasting and Tuscan dinner in the Chianti hills — perfect for those who prefer a slower pace and golden-hour magic (PISA NOT INCLUDED IN THE OPTION)
Reviews(219)
To start with, Tania, what a beautiful woman. Personable, knowledgeable, caring & sharing. Her care & understanding today was exceptional. If you’re looking for an experience of a life time then ask for Tania to make it special. Thank you for making our day special. Allan & Colleen, Australia
To start with Tania, what a beautiful lady. Personable, knowledgeable, caring & sharing. Our tour was like a personal tour with only my wife & I on board. Tanya spoke fluent English which helps when you don’t understand Italian. Tania, went over & above helping us all day long with our needs. If you want a fantastic day touring the country side of Florence, then ask for Tania as your host. Thank you so much for making a day special. Colleen & Allan Australia.
Tania was amazing, and every stop was special. The winery, San Giamgnano, and Siena were wonderful.
Grace was an excellent host. She provided many fun facts and stories about all of the places we visited. She did a great job engaging in conversation with us throughout the day. She was prompt, professional, and definitely added to our overall experience.
Memories and history all in one experience. This was a great tour. We got to visit all these great spots and enjoy the stories of their history, I would highly recommend.
We enjoyed our day with Romana. She was very knowledgeable and helpful and a very nice personality.
Fantastic day we loved our tour so much
Amazing day! Romana was a great guide for the day!!
Tanya, our guide was amazing! The sites and experiences were great!
Our guide, Daria, was a great guide and driver throughout our tour. She brought us to a winery in San Gimignano where the sommelier showed us their wine collection. The food and wine pairings were wonderful! Touring Pisa, San Gimignano, and Siena was truly an awesome experience, and I recommend this tour to any first-timer to Tuscany.
