Top Tuscany Sidecar Tours

Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable private driver, travel through the renowned Chianti wine region to visit the towns of Siena and San Gimignano. See famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano.

Tick off several of Tuscany's most renowned locations during this full-day Vespa tour. Enjoy a photo stop and farm visit at Fattoria Poggio Alloro and take a guided stroll through the picture-perfect village of San Gimignano, with free time to explore. Tours include a three-course lunch paired with a tasting of nine local wines at Tenuta Torciano.

See all that Tuscany has to offer on this day trip to Pisa, Siena, and San Gimignano from Florence. Led by an expert guide, explore the main square and Gothic cathedral in Siena, followed by a traditional, 3-course lunch with wine pairing. Afterward, enjoy free time to stroll the medieval streets of San Gimignano independently, as well as the city of Pisa, famous for its UNESCO-listed Leaning Tower. Your full day of sightseeing concludes with transportation back to Florence.

Discover some of the highlights of Tuscany on this day trip from Florence by coach. Visit historical hill towns Pienza, Montalcino, and Montepulciano; admire the gorgeous, vineyard-covered scenery of Orcia Valley (Val d’Orcia); and enjoy cheese and wine tastings as you stop at local wineries and other venues. It’s a great day out in the Italian countryside.

Explore the Tuscan countryside in true Italian style — on a Vespa! After a short van ride from Florence and a riding lesson, spend a full day zipping along scenic country roads from the seat of your own personal Vespa. Pass by historic vineyards, villas and olive groves while your guide shares insight into local history and culture. Tour an organic farm and winery in the famed Chianti Rufina region, where you’ll enjoy a traditional Tuscan lunch and wine tastings.

Soak up a unique view of Tuscany on this Vespa tour departing from Florence. Led by an expert guide, journey out of the city and hop onto your scooter once you reach the beautiful country roads of Chianti. Stop for a traditional Tuscan meal at a Farmhouse, you’ll enjoy a tasting of local olive oils and prominent Chianti wines while visiting a famous winery. Your Vespa tour will conclude back at your original departure point in Florence.

Leave the crowds of Florence behind and explore the peaceful hills of Chianti hassle-free with this wine tour that includes transportation directly from the city. Take in views over the rolling vineyards during the drive and stop for tastings at two different independent wineries. Connect with the winemakers as you stroll through the estates and sample a number of Tuscany wines paired with local nibbles while relaxing on panoramic terraces.

Marvel at the beauty of the Chianti hills from above with this balloon ride that takes off from the heart of Tuscany. Meet your pilot near the village of San Casciano in Val di Pesa for boarding and float up to a height of 2,000 feet (609 meters) for bird’s-eye views over the vineyards, olive groves, woods, and villages. After landing, toast to your flight with a glass of Champagne.

Discover the Tuscan countryside on this all-day horseback riding tour. Designed for experienced riders, you’ll explore the wild region of Maremma Toscana, crossing wooded areas and small rivers and traveling past medieval villages. The horses are reliable and sure-footed; there are several opportunities to trot and canter. A picnic lunch is included.

Zip through the streets and squares of Florence in true Italian style — in the sidecar of a vintage motorcycle. A driver handles all the sharp turns and navigation so you and a companion can enjoy the ride and all the Renaissance sights. Access smaller alleyways where cars can’t go, and take to the Florentine hills for panoramic views.

Immerse yourself in a five-hour tour where wine lovers can experience the best of Florence and Chianti from a sidecar. Meet winemakers along the way, as you visit a working winery to explore its production processes. Then, enjoy limitless savory tastings or even a Tuscan lunch, if your palate desires it. As you explore the vineyards on this sidecar adventure, you'll be able to snap shots of timeless countryside views.