Siena and San Gimignano
Immerse yourself in the storybook landscapes of Tuscany on an exclusive private day trip from Florence, discovering the Gothic splendor of Siena, the walled fortress of Monteriggioni, the rolling vineyards of Chianti, and the iconic medieval towers of San
The Tour
Leave Florence behind for an unforgettable journey through the rolling, sun-drenched hills of central Tuscany. Your private English-speaking driver greets you directly at your hotel lobby in a premium luxury vehicle, escorting you south past cypress-lined roads toward the historic hill city of Siena, Florence's great medieval rival.
Your morning is devoted to the Gothic wonders of Siena, centering on the shell-shaped Piazza del Campo. Stand in awe of this grand public space and the soaring Torre del Mangia, learning how the square transforms twice each summer into the thunderous arena for the centuries-old Palio delle Contrade horse race. From the piazza, a short stroll brings you to the magnificent Siena Duomo, a Romanesque-Gothic architectural triumph famed for its dramatic black-and-white striped marble facade, intricately inlaid marble floor mosaics, and masterpieces by Donatello, Pinturicchio, and Michelangelo.
Continuing through the picturesque Tuscan countryside, a short drive brings you to Monteriggioni, an extraordinarily preserved thirteenth-century citadel perched atop a gentle hillside. Mentioned by Dante in the Divine Comedy, this fairytale village remains entirely enclosed by its original circular stone curtain walls and watchtowers, surrounded today by peaceful olive groves and vineyards. Here, pause for a relaxed Tuscan lunch at an authentic local trattoria, savoring regional specialties alongside local wines.
In the afternoon, your scenic route winds through the rolling hills of Chianti, Italy's most celebrated wine territory, on your way to San Gimignano. Known as the "Manhattan of the Middle Ages," this breathtaking UNESCO World Heritage site is famous for its iconic skyline of preserved medieval stone towers. Spend a leisurely afternoon exploring the historic center, browsing artisan ceramics and leather workshops, lingering over world-champion gelato in Piazza della Cisterna, and taking in sweeping views over the Val d'Elsa. After an enriching day immersed in Tuscan heritage, architecture, and scenic countryside, sit back and unwind as your driver escorts you comfortably back to your hotel in Florence.
Your morning is devoted to the Gothic wonders of Siena, centering on the shell-shaped Piazza del Campo. Stand in awe of this grand public space and the soaring Torre del Mangia, learning how the square transforms twice each summer into the thunderous arena for the centuries-old Palio delle Contrade horse race. From the piazza, a short stroll brings you to the magnificent Siena Duomo, a Romanesque-Gothic architectural triumph famed for its dramatic black-and-white striped marble facade, intricately inlaid marble floor mosaics, and masterpieces by Donatello, Pinturicchio, and Michelangelo.
Continuing through the picturesque Tuscan countryside, a short drive brings you to Monteriggioni, an extraordinarily preserved thirteenth-century citadel perched atop a gentle hillside. Mentioned by Dante in the Divine Comedy, this fairytale village remains entirely enclosed by its original circular stone curtain walls and watchtowers, surrounded today by peaceful olive groves and vineyards. Here, pause for a relaxed Tuscan lunch at an authentic local trattoria, savoring regional specialties alongside local wines.
In the afternoon, your scenic route winds through the rolling hills of Chianti, Italy's most celebrated wine territory, on your way to San Gimignano. Known as the "Manhattan of the Middle Ages," this breathtaking UNESCO World Heritage site is famous for its iconic skyline of preserved medieval stone towers. Spend a leisurely afternoon exploring the historic center, browsing artisan ceramics and leather workshops, lingering over world-champion gelato in Piazza della Cisterna, and taking in sweeping views over the Val d'Elsa. After an enriching day immersed in Tuscan heritage, architecture, and scenic countryside, sit back and unwind as your driver escorts you comfortably back to your hotel in Florence.
Flexibility
Itinerary and pace managed directly with your private driver
Services include pickup from and drop-off back at either your hotel or at your cruise ship in one of our luxury vehicles by an English-speaking driver.
Lunch, gratuities, and any entrance fees to attractions are not included. Also please note that we may change the order of the itinerary at our discretion.
Multiple booking discounts are available when you book more than one tour or excursion with us. Please note that these discounts do not apply to airport or port transfers.
This tour is suitable for families with children, with a comfortable pace and private service that makes the day easier to enjoy together.
