Overview
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.
What's included
- ✓English-speaking driver/tour leader
- ✓Free time in San Gimignano
- ✓Free Wi-Fi on board
- ✓Winery guided tour with wine tasting
- ✓Guided walking tour of Siena with professional licensed guide
- ✓Round-trip transportation from Florence by luxury Mercedes Minivan or Minibus
- ✓Visit Pisa & Miracle Square - NO Leaning Tower tickets (NOT INCLUDED IN THE AFTERNOON OPTION)
- ✓3 course Typical Tuscan lunch or Dinner for the Afternoon Siena & San GimignanoOption
- ✓Surprise tasting in Siena or San Gimignano
- ✕Gratuities
- ✕Hotel pickup and drop-off
- ✕We are sorry to inform you that pets are not permitted on our tours
- ✕Pisa Leaning Tower (Entry Tickets not included)
What you'll do
- 1
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.
⏱ 30 min - 2
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.
⏱ 1 hour - 3
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.
⏱ 30 min - 4
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.
Availability & pricing
Operates on
Price from (per person)
$167
$142
$142
4 tour options available. Pick your exact date & check live availability on the booking page.
Good to know
- 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)
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Tour details & pricing provided by Viator. Bookings are completed on Viator.com.
