The Experience

Chianti to Montalcino, the Birthplace of Brunello

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 the wines, flavors and luxuries you’ll discover.

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 critically acclaimed regional wines

Discover idyllic hilltop towns brimming with medieval and Renaissance architecture


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 Cruise the ridge to the ancient hilltop town of Radda, long the center of Chianti wine production The hidden nooks of Via delle Volte, Castellina’s unique arcaded passageway, are a delight to explore Visit Badia a Coltibuono (Abbey of the Good Harvest), where you’re treated to a private tour and olive oil tasting Wine and 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, known for harboring the region’s finest wines, are yours to discover Point your wheels toward southern Tuscany, where stately cypresses crisscross open rolling hills Taste world-famous Brunello 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.


The Route

Start with our vacation planner so we can match you with our most suitable travel advisor. We do it all for you, air, car, accommodations, tours, you name, it in a seamless luxury vacation experience you will treasure for a lifetime.