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Experience the best combination of gourmet meals, great wine and scenic cycling! Chef Fabio Flagiello, a Michelin-award winning chef, and Tuscan native, will prepare all meals from fresh, locally sourced ingredients and offer two cooking workshops during the week. Enjoy challenging, daily rides between 30–60 miles through Tuscan farmland, vineyards, and historic villages. If you want to hammer on the bike to make more time for wine tasting, this tour is for you!
You’ll stay at town of Radda in Chianti, in a luxurious private villa, complete with private rooms and bathrooms, outdoor dining, a lounge pool and scenic, countryside views. This tour week is reserved for a private party of 8 - 12 people. Recruit friends and family for this once-in-a-lifetime immersive Italian culinary and cycling classic! Contact us at [email protected] to get started. 
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itinerary |
cuisine |
lodging |
preparation |
Itinerary
- 1.30pm - Pickup at main train station in Florence (outside at the bus pick up, left of the main entrance facing the station) at the Hotel Una Vittoria
- 3.00pm - Arrive at Villa in Chianti, just north of Siena
- 6.30pm - Welcome Aperitivo at the Veranda
- 8.00pm - Dinner at the Villa
- 8.00am - Breakfast at the Villa
- 9.00am - RIDE 40 MILES to the Abbazia di San Galgano and back; we'll be riding on “Colli Senesi” or the rolling hills of Siena
- 12.00pm - Picnic lunch at Abbazia
- 1.00pm - Ride back to the Villa
- 5.00pm - Cooking class
- 8.00pm - Dinner on the Veranda
- 8.00am - Breakfast at the Villa
- 8.30am - Transfer to Chianti
- 9.30am - RIDE 45 MILES around the Chianti Region
- 1.00pm - Visit at Gaiole di Chianti, home of the Eroica; Picnic lunch at Castello di Brolio
- 5:00pm - Shoe shopping at Pratesi factory
- 6.00pm - Return to van for drive back to the Villa; Stop for pizza at a local pizzeria along the way
- 9.00pm - Back at the Villa
- 8.00am - Breakfast at the Villa
- 9.00am - RIDE 40 miles west to Volterra, land of Boccelli, featuring rolling hills with a climb into the last town - a Tuscan classic!
- 1.00pm - Lunch in Volterra
- 2.00pm - Ride back to the Villa
- 7.00pm - Aperitivo at the Villa
- 8.00pm - Dinner at the Villa
REST DAY
- 9.00am - Breakfast at the Villa
- 10.00am - Departure for Montalcino
- 11.00pm - Arrival at Ciacci Piccolomini d’Aragona, Lunch at Brunello Winery, followed by caffe in downtown Montalcino
- 4:00pm - Departure for Siena
- 5.00pm - Date Night: Visit downtown Siena and dinner on your own
- 9.00pm - Meet at the Square to drive back to Villa
- 8.00am - Breakfast at the Villa
- 9.00am - RIDE 30 miles to Castello di Monteriggioni, lots of rolling hills and a beautiful climb at the end
- 1.00pm - Lunch at the Villa
- 2,00pm - Relaxing afternoon poolside
- 6.00pm - Cooking class at the Villa
- 8.30pm - Dinner at the Villa
- 8.00am - Breakfast at the Villa
- 9.00am - RIDE 50 miles to San Gimignano with lunch on the route
- 12.00pm - Visit in San Gimignano
- 2.00pm - Return to Villa via bicycle or van
- 8.00pm - Notte Finale Wine Dinner with special guests Casole d’Elsa Mayor and locals
- 9.00am - Breakfast at the Villa and last chance to relax poolside
- 11.00am - Depart to Florence train station
- 12.00pm - Arrive at Florence train station
Cuisine
- Two cooking workshops at the Villa with Chef Fabio
- Lunch at restaurants along the route handpicked by Chef Fabio
- Private dinners on the Veranda at the Villa, with all preparations by award-winning Chef Fabio
- Celebratory dinner on the last evening with wine pairing by local winemaker and special host of the evening
lodging
You’ll stay at town of Casole d'Elsa, Villa ai Casini, https://www.vacavilla.com/it/casa-vacanza/podere-i-casini/, a luxurious private villa, complete with private rooms and bathrooms, outdoor dining, a lounge pool and scenic, countryside views. Our group will have the entire Villa to ourselves for the whole week, complete with individual rooms, private bathrooms, and free Wi-Fi. The villa features a swimming pool, outdoor veranda for dining with exquisite views, professional kitchen, and walking gardens – a wonderful, relaxing place to spend a rest day, or for your partner to stay while the group is riding.
Preparation
With daily routes averaging between 30 - 60 miles and 3,000+ feet of elevation gain, Cycling Tuscany is challenging but fun for both social and serious cyclists. Terrain varies between the vineyards and olive groves of the rolling countryside to climbs of 5-7 miles averaging 2-4% grade. Tuscany has quite a bit of climbing as well, with sections of ascent and descent up to 12% grade. All roads are paved asphalt, perfect for road bikes. In addition to breathtaking vistas, small medieval towns, and historic buildings along quiet winding roads, guests will enjoy meeting local riders and former pro cyclists who serve as guest leaders on several days of this tour, providing a level of intimacy like no other tour!
Leading up to the trip, we recommend that guests are consistently riding 3+ days a week for 25-40+ miles so that they are comfortable in the saddle for 3–4 hour rides. Riders should be accustomed to climbing and descending, as well as bike handling on hills and curved roads.
Leading up to the trip, we recommend that guests are consistently riding 3+ days a week for 25-40+ miles so that they are comfortable in the saddle for 3–4 hour rides. Riders should be accustomed to climbing and descending, as well as bike handling on hills and curved roads.
