Travel Guides: Italy Travel Guide: Overview
In Southern Europe—right in the heart of the Mediterranean—lies a boot-shaped country stuffed to the brim with culture, history and fine cuisine.
Couples, Friends & Solos
6 days 5 nights
Activity Levels 2-4
From: $5,999 - $6,299 pp dbl occ
($1,500 for sgl occ)
Tuscany is not only a destination, it's a sublime experience. Pause on the cypress-lined roads that overlook the vineyards and take it all in. You'll think that no view will compare to that view, until you round the next bend and see another. It's a wonder anyone ever finishes the bike rides. And this is only a preview of what you'll see. Imagine the wines, flavors and luxuries you'll discover.
Start Arezzo / End Florence
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Embark on a quintessential Tuscan adventure, riding scenic routes in the Chianti Classico wine region | Spin through the rolling countryside and take in the sweeping vistas—you’ll soon realize why this is one of the most famous regions in the world | Sample local specialties at an organic agriturismo before biking past olive orchards and vineyards | Ride toward the heart of the Chianti, passing through legendary wine villages like Gaiole in Chianti and Castelnuovo Berardegna | Cycle into the Crete Senesi, an area known for its lunar landscape | Explore Siena’s medieval back streets and grand Piazza del Campo, home to Italy’s most important horse race, Il Palio | Learn the nuances of Tuscany’s renowned red wines at an exclusive sommelier-led tasting.
Ride the ridge to ancient hilltop Radda, former capital of the Antica Lega del Chianti (Old Chianti League) | Visit the picturesque neighboring village of Castellina in Chianti | Cycle along a breezy downhill route with unsurpassed views of Siena and San Gimignano in the distance | Celebrate in Tuscan style over dinner | Bike to Colli Fiorentini, northern Tuscany's slice of Chianti wine production | Follow cycling routes in the verdant Elsa River Valley to the spectacular World Heritage town of San Gimignano, crowned by 13 towers | Toast la dolce vita with a glass of refreshing Vernaccia, Tuscany's most famous white wine, before heading to Florence.
A castle-turned-Renaissance villa steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)
The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy
Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy.
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.
The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Read on for bike options specific to this trip (click the arrow to see more). Please note that bike requests are subject to availability and prioritized based on the date they're submitted.