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 Level: 2-4
Premiere Hotels
From: $6,199 - $6,699 pp dbl occ
($1,750 - $2,300 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 Berardenga | 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.
Experience the essence of Chianti at this hilltop retreat encircled by the quiet Tuscan countryside. World Luxury Hotel Awards winner. (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 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 in USD.
Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.
Group size is required to show per-person pricing. Your group size can be approximate and can change.
Share your adventure #MyBackroadsTrip
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! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.
Click the arrow to see all bike options.
Included in your trip price
This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork.
Included in your trip price
A proven classic, this custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.
Included in your trip price
Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+
Ride like a pro with the top-of-the-line carbon Cannondale Synapse Hi-Mod Red ETAP AXS. Delivering phenomenal acceleration and handling in a light and powerful package.
$650 rental fee; subject to availability
This hand-built frame features Co-Motion's custom-designed cro-moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train, and a custom, upgraded wheelset. For experienced tandem riders.
$400 rental fee
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.
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