Tuscany Wine Country Bike Tour
6 days
5 nights
Activity Levels 2-4
Premiere Hotels
Tuscany Wine Country Bike Tour
6 days
5 nights
Activity Levels 2-4
Premiere Hotels
2024: Oct 2025: May-Jun, Sep-Oct
Cuisine, Culture & Chianti in the Heart of Italy
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.
Highlights
- Bike our favorite Tuscan roads—with ample van support, of course—as we wind our way from breathtaking Chianti to remarkable Crete Senesi and beyond
- Luxuriate at handpicked hotels that represent Tuscany's finest, from elegance in Chianti to unforgettable COMO Castello del Nero
- Taste Chianti Classico and Vernaccia, among other critically acclaimed regional wines that have been cultivated in the region for hundreds of years
- Discover idyllic hilltop towns like San Gimignano and Siena, brimming with character and stunning examples of medieval and Renaissance architecture
Start Arezzo
End Florence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
Days 1-3
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.
Nights 1-3
Experience the essence of Chianti at this award-winning hilltop retreat encircled by the quiet Tuscan countryside. (pool, spa)
Days 4-6
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.
Nights 4-5
Relax at a castle that has been converted into a Renaissance villa, steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)
What's Included
See moreHotels
World-Class Hotels
Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
Nights 1-3
Premiere Hotel
Experience the essence of Chianti at this award-winning hilltop retreat encircled by the quiet Tuscan countryside. (pool, spa)
Nights 4-5
Premiere Hotel
Relax at a castle that has been converted into a Renaissance villa, steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)
Gallery
Bikes
Choose Your Perfect Bike
Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.
Included in your trip price
- Ideal for avid cyclists
- Redesigned for 2024
- Next gen titanium frame with carbon wheels
- Responsive, efficient and comfortable
- Drop handlebars only
Included in your trip price
- Suited for a wide range of cyclists
- Comfortable ergonomic seat
- Long wheel base adds to the bike's control and stability
- Upright handlebars only
Included in your trip price
- One of the lightest e-bikes available
- Provides plenty of power and more than enough battery
- Lower top tubes for easier mounting and dismounting
- Upright handlebars only
- Limited availability on Unplugged Bike Tours; learn more
Min. age to ride e-bike: 16+
- $400 rental fee
- Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train
- Custom upgraded wheelset
- Best for riders with some tandem experience.
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
Please Select a Group Size
Group size is required to show per-person pricing. Your group size can be approximate and can change.