Cycling Tuscany
September 9 - 16, 2023
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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 in a luxurious private villa, complete with private rooms and bathrooms, outdoor dining, a lounge pool and scenic, countryside views. We are offering special pricing of $6,000 per couple for this tour! 
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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) ot the Hotel Una Vittoria
- 3.00pm - Arrive at Villa in Casole d’Elsa, just north of Siena and east of Chianti
- 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 San Gimignano, mostly rolling hills - a Tuscan classic!
- 1.00pm - Lunch and passeggiata in San Gimignano, optional to drive or ride back to the Villa
- 7.00pm - Aperitivo at the Villa
- 8.00pm - Traditional Tuscan Menu featuring Ribollita Soup, Pici, (everyone is always welcome to cook with Chef Fabio)
- 8.00am - Breakfast at the Villa
- 9.00am - RIDE 45 MILES east to the Castello di Monteriggioni
- 1.00pm - Lunch at the villa
- 5:00pm - Cooking Class: basics and cooking theory
- 8.00pm - Dinner on the Veranda
- 8.00am - Breakfast at the Villa
- 9.00am - Ride in Chianti, 50 MILES of rolling hills including paved roads and "strade bianche" (gravel)
- 1.00pm - Pic-nic Lunch in Gaiole home of L'Eroica
- 2.00pm - After lunch we will ride to Castelnuovo di Berardenga and then jump into the vans and drive back to the Villa
- 7.00pm - Aperitivo at the Villa
- 8.00pm - Pizza at the Villa
REST DAY
- 9.00am - Breakfast at the Villa
- 10.00am - Departure for Montalcino
- 11.00pm - Tour & Lunch at the Brunello Winery, Ciacci Piccolomini, Espresso in downtown Montalcino after lunch
- 3:00pm - Departure for Siena
- 4.00pm - Visit downtown Siena and Date Night (dinner on your own)
- 9.00pm - Meet at Van to drive back to Villa
- 8.00am - Breakfast at the Villa
- 9.00am - RIDE 45 miles to Volterra, lots of rolling hills and a beautiful climb at the end
- 2.00pm - Lunch at the Villa
- 3,00pm - Relaxing afternoon poolside
- 5.00pm - Cooking workshop (gnocchi and more)
- 8.00pm - Dinner and Vin Santo at the Villa
- 8.00am - Breakfast at the Villa
- 9.00am - RIDE 45 miles, loop to the Basilica di San Galgano “the open air church from 1200 century”
- 12.00pm - Lunch pic-nic, and back to the villa
- 6.00pm - Aperitivo at Roccie di Casole Winery
- 8.00pm - Notte Finale Wine Dinner with Paolo Caciorgna, owner and winemaker of Roccie di Casole, and Chef Fabio
- 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 2–3 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 2–3 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.
