Top Tuscany Motorcycle Tours

Explore the rolling hills, sun-blushed vineyards, and winding country lanes of Tuscany from a classic Italian Vespa. Hop aboard your own 50cc Original Piaggio Vespa scooter or share one with a friend, and follow your guide on a scenic tour of the Chianti region. Enjoy the views of the skyline of the Medieval walled city of San Gimignano, jump off to admire the views, and enjoy a delicious wine-tasting lunch at a Tuscan winery.

Knowing where to visit in the Tuscan countryside can be daunting for first-timers, especially if you're starting off in Florence. Simplify your day out with this group tour. Once you've boarded your coach, sit back knowing the transportation and activities are covered, meaning you can fully immerse yourself in the experience. Enjoy visiting Pienza, Montalcino, and Montepulciano, the Orcia Valley, and taking part in a wine and cheese tasting.

Get off of crowded tour buses and behind two wheels of a zippy Vespa on this “ultimate” tour of Chianti. After a short skill check test at our base, explore the Tuscan countryside and Chianti hills past vineyards, olive tree groves, and rural villas. A small group means more attention from your guide. Then, ride the scenic Chianti Road on the return journey.

Set off on a Vespa adventure to discover Fiesole and its stunning landscapes, where history and nature meet. Ride a vintage-style Piaggio Vespa through the Tuscan hills near Florence, surrounded by vineyards and olive groves. After a short test ride, follow your guide to Fiesole to explore the town and admire views over Florence. If the shared guided tour is selected, enjoy a visit to a local olive oil producer with a tasting of premium extra virgin olive oil, a perfect blend of flavor, scenery, and fun.

Embark on a magical journey in Tuscany with this 4-5 hour private Chianti motorcycle tour from Florence. Hop aboard the Moto Guzzi V85TT, and get ready for an unforgettable experience through one of Italy's most beautiful regions. Soak up the culture, explore ancient castles, and marvel at the scenic vineyards of Montefioralle village before trekking off down dirt roads made famous by L'Eroica; Greve In Chianti, Panzano In Chianti, and Radda Enroute until you reach Castellina In Chianti.

Hi, I'm Paso — a motorcyclist and a dreamer. I invite you to join me aboard an Indian Roadmaster for a genuine journey far from the usual tourist routes, deep into the most heartfelt emotions of Tuscany. Every ride is unique. There’s no fixed itinerary — we’ll decide together where to go, based on your interests and curiosity: the rolling hills of Val d’Orcia, hidden villages, and roads I’ve known my whole life, far from the crowds. I’ll be your personal guide — like traveling with a friend who’s showing you the places he holds closest to his heart. Along the way, we’ll stop where the light is just right, where the earth smells sweet, where it’s worth taking a breath. I’ll share my story — and if you like, I’ll listen to yours. It’s a sensory, emotional, and intimate journey. It’s IndianBikeTherapy

See what Tuscany has to offer without breaking the bank on this budget-friendly day trip to the region's highlights from Florence. Save hours with coach transportation and enjoy free time to explore the medieval old towns of Siena and San Gimignano, plus the sights of Pisa. Upgrade to a guided tour of Siena, or add-on a 2-course lunch with wine pairing for a hassle-free, all-inclusive day.

Experience the true flavor of the Tuscan countryside—and enjoy wine tasting without designating a driver—on this Chianti wine tour from Florence. Visit local wineries in scenic villages to sample revered Tuscan wines and learn winemaking secrets. Alternatively, enhance your day with a morning cooking class preparing traditional Tuscan recipes paired with premium wines.

Get a taste of Tuscany's culinary legacy on this wine and food tour from Florence. Led by a sommelier guide who provides insights that you'd miss on your own, travel through the Tuscan hills in a 4WD vehicle, stopping to visit historic wine estates and cellars along the way. Sample specialities at each stop, and enjoy a 3-course meal in the Tuscan countryside before returning to Florence.

Discover the many delights of Tuscany’s wine country on this small-group tasting tour from Florence. Travel along beautiful hillside roads through vineyards, olive groves and cypress trees. Visit 2 top-rated wineries in the famed Chianti Classico region, tour the cellars and learn how wine is produced using traditional methods. Taste different wines, along with olive oil and Tuscan specialties like fresh cheeses and bruschetta. Group size is limited to twenty-five participants for a more personalized experience.

Explore the Tuscan countryside in true Italian style—on a Vespa! Spend the morning zipping along scenic country roads from the seat of your very own two-wheeler. Cap off your ride with a traditional Tuscan lunch before heading back to Florence. Or, opt for the afternoon tour to witness a stunning Tuscan sunset along with a wine tasting and snack.

Do you want to live a unique experience riding a professional driver? We will ride my Moto Guzzi V85TT together on one of the most beautiful and richest roads in Tuscany: the Setteponti. This road, which follows the ancient Roman road Cassia Vetus, includes not only hundreds of fun curves but also numerous parish churches, ancient villages and beautiful landscapes on the Arno valley. We will visit the Parish Church of Pian di Scò whose history and curiosities I know. We will stop in Loro Ciuffenna for a walk through its streets and a wine tasting (optional tasting and excluded from the price). We will cross the Le Balze Natural Area, where I will tell you the story of their formation and their connection with Leonardo da Vinci, along a little known road until reaching a non-touristy Chianti area.

Florence's finest views are found on top of the hills that surround the city, but reaching Piazzale Michelangelo, San Miniato, and Fiesole on foot can eat up most of a day. This classic Vespa sidecar tour covers all three at an easy pace, with a driver who knows the best spots to pull over for photos.

Explore Quaint Villages and Timeless Landscapes Our journey will take you off the beaten path, winding through both lesser-known hamlets and iconic landmarks alike. Immerse yourself in the rich history and culture of each village we visit, from hidden gems tucked away in the countryside to well-known destinations steeped in tradition. Capture Every Moment, Embrace Every View As we traverse the rolling hills and winding roads, there will be ample opportunities to pause and soak in the panoramic views. Experience the Joy of Open-Air Travel Feel the sun on your face as you cruise through the Val d'Orcia on your Vespa. This isn't just a tour – it's an immersive journey into the heart of Tuscany's natural beauty. Let the open road be your guide as you embrace the freedom of outdoor exploration. Don't Miss Out on This Unforgettable Experience Join us for a Vespa adventure like no other and discover the magic of Val d'Orcia in a whole new way.