Few things in this world live up to the hype. But everything you've ever heard about Tuscany is true. It's not a destination. It's a sublime experience. Routes lined with cypress trees overlooking the patchwork vineyards below will stop you on your bike. And no view will compare to that view. Until you round the next bend and see another. It's a wonder anyone ever finishes the rides. And that's only what you'll see; imagine all the flavors and luxuries you'll discover.
Day 1 The quintessential Tuscan journey, offering the most scenic routes from Florence to Montalcino Sample fresh Tuscan specialties at an agriturismo before biking serene roads past olive orchards, farmhouses and wheat fields Pedal to medieval Greve in Chianti, where you can stroll through the narrow lanes and pretty piazza of this former market town before continuing to the splendid Castello del Nero.
Days 2-3 Ascend quiet roads into the heart of the Chianti region The hidden nooks of Via delle Volte, Castellina's unique arcaded passageway, are a delight to explore Cruise the ridge to the ancient hilltop town of Radda, long the center of Chianti wine production Visit Badia a Coltibuono ("Abbey of the Good Harvest"), where you're treated to a private tour and olive oil tasting Dine in style at San Felice's renowned restaurant.
Day 4 Visit Monte Oliveto Maggiore, a Benedictine abbey featuring some of the best preserved frescoes in Europe Our route leads through the chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine paintings Stroll Montalcino's medieval streets in search of the perfect trattoria for dinner.
Days 5-6 The narrow streets of Montalcino are yours to discover Point your wheels toward southern Tuscany, where stately cypresses crisscross open rolling hills Pedal through the undulating wheat fields and hilltop towns of the Val d'Orcia In Pienza, marvel at extraordinary Renaissance architecture and sample splendid pecorino cheese Visit the imposing abbey of Sant'Antimo, where monks celebrate mass with stirring Gregorian chants.
- Ride, relax and savor every drop of this vintage Backroads experience
- Pedal our favorite Tuscan roads with ample shuttle support
- Luxuriate at handpicked hotels that represent Tuscany's finest
- Taste regional specialties like pecorino cheese and olive oil
- Discover idyllic hilltop towns brimming with medieval and Renaissance architecture
Castello del Nero (2 nights): A castle steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)
Relais Borgo San Felice (2 nights): Described by the Hideaway Report as an "enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region." A Relais & Châteaux member. (pool, spa, tennis)
Castello di Velona (1 night): Soak up superb hilltop views at this elegant 11th-century fortress featuring a magnificent vantage point above the Val d'Orcia. A Small Luxury Hotels of the World member. (pool, spa)
Every Backroads trip is designed to appeal to a wide variety of
interests and fitness levels. We know your pace may vary from one
day to the next-and your traveling companion's may differ somewhat
from yours. So we present a range of mileage options, and each
day you decide exactly what and how much you want to do.
Routes For All Abilities
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* Includes a shuttle
Private Trips Options & Pricing
Guest Trip Reviews
Tuscany is synonymous with ageless scenery, fascinating history and delectable cuisine. And an ideal way to experience it is by bike with Backroads. You'll enjoy rich and authentic experiences that are a result of years of research and cultivated relationships. We look forward to introducing your whole family to the wonderful places and welcoming people that make this region so special.- Regional Coordinator, Italy