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.
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 rides. And this is only a preview of what you'll see. Imagine the wines, flavors and luxuries you'll discover.
THIS ITINERARY: 6 days, 5 nights
ACCOMMODATIONS: Premiere Hotels
Start Arezzo / End Florence
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Embark on a quintessential Tuscan journey on scenic bike routes in the Florentine countryside | Sample local specialties at an agriturismo before biking past olive orchards and vineyards | Follow the Via dei Sette Ponti (Road of Seven Bridges) through well-kept villages to our historic hotel.
This family-owned hotel resides in a stunning setting atop a narrow ridge and features an acclaimed winery. A Relais & Châteaux member. (pool, spa)
Descend into the Arno River Valley as you ride toward the heart of the Chianti, passing through legendary wine villages like Gaiole in Chianti | Bicycle 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.
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)
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 | Celebrate in Tuscan style with a Michelin-starred dinner at La Torre, our hotel's superb restaurant | 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 with a Michelin-starred restaurant 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. 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. LEARN MORE.
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 your available bike options for this trip.
We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.
Il Borro is a Premiere Hotel. While it offers outstanding service and amenities, please note that it is not equipped with air-conditioning. Despite the region's generally temperate climate and cool nights, guestrooms can occasionally become warm during peak temperatures.