• Florence - Join the tour leader at 7:45 AM in Piazza Mentana, right outside the Towns of Italy Office. After a warm welcome, depart at 8:00 AM in a luxurious Mercedes minivan (maximum 8 guests) featuring A/C and complimentary Wi-Fi. Prepare to unwind and enjoy the scenic views of the Chianti countryside, adorned with cypress-lined roads, olive groves, and historic villas. The expert driver will outline the day’s itinerary as you embark on your memorable Grand Tour of Tuscany.
• Siena - Upon arrival in Siena, meet your local licensed guide for an engaging walking tour through one of Tuscany’s most historic cities. Explore the Basilica of San Domenico, stroll along medieval streets like Via della Sapienza and Piazza Salimbeni, and admire the noble palaces on Via Banchi di Sopra. Discover Piazza Tolomei and enter the grand Piazza del Campo, renowned for the Palio horse race. Continue past the Battistero and finish at the magnificent Duomo, all while learning about Siena’s Contrade and its rich cultural heritage.
• Siena - Before departing Siena, enjoy a delightful local tasting experience curated by your guide. Relish traditional Tuscan flavors such as cantucci with Vin Santo, ricciarelli, or other seasonal specialties that showcase the region’s rich culinary heritage. This moment offers a delicious introduction to the day’s culinary highlights and a unique chance to indulge your senses in the heart of medieval Tuscany.
• San Gimignano - Continue your journey along the scenic Via Cassia, passing charming villages like Monteriggioni and Colle Val d’Elsa, until you reach San Gimignano. Known as the “medieval Manhattan” for its towering structures, this UNESCO World Heritage town offers stunning views and timeless allure. Enjoy FREE TIME to explore artisan shops, taste Vernaccia wine, admire frescoed churches, or climb Torre Grossa for a panoramic view—it’s your Tuscan postcard come to life.
• Strada in Chianti - Delight in a traditional Tuscan lunch at a carefully chosen trattoria or farmhouse in the Chianti region. Savor regional specialties 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 a picturesque rural setting, perfect for relaxing and embracing the Tuscan lifestyle before heading to your final destination.
• Pisa - Arrive in Pisa and enjoy free time in the iconic Piazza dei Miracoli. Marvel at 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, they can be purchased on-site if time allows. Capture your perfect Pisa photo before boarding the minivan for the final leg of your journey. Return to Florence by 7:30 PM, filled with memories from a day rich in art, history, flavors, and unforgettable views.

• 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 Gimignano Option
• 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)

Prepare for an exceptional Tuscan day trip, exploring the region’s most renowned towns, breathtaking landscapes, and globally celebrated flavors.

Start your adventure from Florence in a luxurious minivan, accompanied by an expert tour leader. The journey begins in Siena, where a guided walking tour unveils medieval streets, Piazza del Campo, and the traditions of the Contrade. Delight in a surprise local tasting before proceeding to San Gimignano, the hilltop town known for its towers, where you can enjoy free time to explore artisan shops and take in the stunning views. Relax with a traditional Tuscan lunch before arriving in Pisa. Marvel at the Leaning Tower, cathedral, and baptistery in the awe-inspiring Miracle Square.

This Grand Tour offers a perfect mix of art, history, wine, and the charm of the countryside—ideal for travelers seeking a comprehensive and unforgettable day.

Pressed for time? Opt for our afternoon option, featuring Siena, San Gimignano, and a sunset wine tasting with a Tuscan dinner in the Chianti hills—perfect for those who enjoy a leisurely pace and the magic of the golden hour.

• 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)

For a full refund, cancel at least 24 hours before the scheduled departure time.