The 7 Best Italy Wine Tours for Cycling Your Way Through Vineyards

Best classic Italian wine tour: The Wine Ride

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• Duration: 1 day
• Starting point: Florence
• Ending point: Florence

Tuscany’s Chianti wine region is probably the most famous in Italy, and The Wine Ride is the perfect Italy wine tour if you’re looking for a relaxed way to see the sights of the Chianti region. From Florence, you’ll be transported to the Tuscan countryside to begin cycling through vineyards, olive groves, and old stone farmhouses, stopping at three popular wineries for tastings. A visit to the medieval town of Castellina in Chianti is also included, as well as a light lunch featuring local food and wine pairings from regional wineries.

Best educational tour: Tuscany Wine Lovers

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• Duration: 1 day
• Starting point: Florence
• Ending point: Florence

The Tuscany Wine Lovers tour isn’t a misnomer — it’s an ideal Italy wine tour for travelers who want to gain some in-depth vinicultural knowledge. From Florence, you’ll be driven to the Chianti countryside to visit medieval towns – with time for some shopping – and take a bike tour that includes three wine tastings. For your first stop, you’ll sample Tuscan wines as well as wines from other regions in Italy. The second stop includes a visit to an antique cantina, accompanied by four wines and a tasting of some local extra-virgin olive oil. The tour ends with a visit to Monteriggioni, a medieval walled village surrounded by olive groves and vineyards, where you’ll enjoy your third wine tasting.

What’s especially unique about this tour is that you won’t be tasting the same wines over and over. You’ll taste your “standard” chianti red blends, as well as sangiovese, and even a vernaccia (a crisp, acidic white) —  not exactly what you expect to find in the Chianti region. This is a great Italy wine tour if you want to learn more about the diversity of wine in Italy’s most well-known wine region (and learn about olive oil production to boot).

Best coastal tour: Tuscany Coast & Wine Bike Tour

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• Duration: 5 days
• Starting point: Volterra
• Ending point: Bolgheri

Centering around the Etruscan Coast, the Tuscan Coast & Wine Bike Tour brings you from Volterra – known for mining and alabaster – to the Tuscan coast. The landscape ranges from sandy beaches to a countryside dotted with olive trees and vineyards. You’ll also be cycling through Bolgheri, a wine region home to the Ornellaia and Sassicaia labels. The highlight, however, is probably the Maremma region, a relatively wild and untouched area of the country.

Best for art lovers: Chianti by Bike

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• Duration: 7 days
• Starting point: Florence
• Ending point: Florence

The weeklong Chianti by Bike tour is a perfect Italy wine tour if you want to spend multiple days exploring Italy’s wine region in a truly comprehensive experience. From Florence, you’ll be driven to Radda, Chianti, t begin cycling. The tour brings you through Siena, San Gimignano, and Certaldo, passing scenic mountain ridges, medieval wineries, gothic cathedrals, vineyards, and olive groves. Gourmet dinners are also included, as are visits to galleries containing priceless art and a visit to the Italy National Wine Museum. So you’ll have your fair share of delectable food and cultural sightseeing in addition to wine.

Some days are spent cycling while others are more about touring on foot, so it’s a good Italy wine tour if you want a longer trip but worry that your legs can’t take a full week of pedaling.

Best for mixed groups: Tuscany Bike Tour

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• Duration: 1 day
• Starting point: Florence
• Ending point: Florence

This short tour is perfect for those who only have one day in Florence or only want a brief wine jaunt through Tuscany. The six-hour Tuscany Bike Tour takes you from Florence into the Chianti hillside, where you’ll ride bikes (either regular or e-bikes) along a route lined with farmhouses, vineyards, churches, and castles. It’s roughly a 10-mile tour and stops at world-renowned wineries, wine cellars, and a local restaurant for lunch with wine pairings from area wineries.

If you’ve never cycled before, opt for an e-bike during the tour — you can pretty much guarantee not having to do much work. But if you do want your Italy wine tour to be about a bit more than just imbibing, choose a regular bike without any e-assist. It’s a great tour for groups with a mix of both experienced and beginner cyclists or groups of different age and fitness levels.

Best for maximizing mileage: Piedmont Wine Country Cycling Tour

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• Duration: 8 days
• Starting point: Torino
• Ending point: La Morra

Known as the “wine capital of Italy,” the Piedmont region is famous for its old-world wines made using traditional methods found nowhere else in the world. The Piedmont Wine Country Cycling Tour takes you along some of the country’s best cycling routes, from Turin south through wine country vineyards, valleys, and meadows. You’ll also see plenty of castles and medieval villages. Expect to indulge in several wine tastings as well as local foods like cheese and specially-cured salami. The tour passes through Alba (famous for its truffles), Barolo, and other small villages, each with its own unique culinary specialties.

Best small-town tour: Montalcino Bike & Wine Tour

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• Duration: 1 day
• Starting point: Montalcino
• Ending point: Montalcino

The one-day Montalcino Bike & Wine Tour loops around the Montalcino countryside. It starts in the old town of Montalcino and passes small villages, vineyards, and the Sant’Antimo Abbey en route to a Brunello winery. There, you’ll enjoy lunch, wine tasting of four or five wines, and a tour of the cellar and barrels, then continue by bike to the nearby village of Castelnuovo dell’Abate. On the way, cyclists can admire views of the Val d’Orcia (a stunning Tuscan valley), known for its olive groves, fields of grains, and rolling hills – before returning to Montalcino. The tour is led by an expert guide and is suitable for all skill levels.