TUSCANY TRAIL
October 12 - 19, 2024
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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. 
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itinerary |
cuisine |
lodging |
preparation |
Itinerary
- 2.00pm - Pickup at Hotel Una Vittoria, Florence
- 3.00pm - Arrive in Pisa, Hotel check in
- 5.00pm - Bike Rental Set Up
- 6.30pm - Welcome Aperitivo at the Veranda
- 8.00pm - Dinner at the Villa
- 8.00am - Breakfast and Day Briefing
- 9.00am - Wheels up, First day of Tuscany Trail Gravel Experience,
- Gaiole, Radda in Chianti, 45 miles, flat course for the first half, rolling for the remaining with final climb to Radda, riding through the towns of San Sano, Monti, Brolio, Pianelle.
- Lunch in Gaiole in Chianti, Home of the Eroica
- 3.00pm - Back to the villa
- 7.00pm - Aperitivo and Dinner at “La Bettola dell'Eroico” in downtown Radda.
- 8.00am - Breakfast and Day Briefing
- 9.00am - Start Ride, Radda, riding through Panzano, Greve, Volpaia, back to Radda, 40 miles, decent to start the ride, main climb after, rolling hills or the remaining of the route, with last climb to Radda.
- Lunch in town
- 3.00pm - Arriving at the Villa
- 7.30pm - Aperitivo and Dinner at the "Boutcher", Dario Cecchini, at his restaurant Solo Ciccia
- Day Off
- 9.00am - Relaxing morning at the villa, Yoga class.
- 10.30am - Brunch
- 12.00 - Departure for a visit at Fonterutoli Winery
- 3.00pm - Departure for Siena
- 4.00pm - Arriving in Siena for "Date night"
- 9.30pm - Meet back in the Square to return at the villa
- 8.30am - Breakfast
- 9.30am -Reversed Eroica Loop, 45 miles, through the town of Vagliagli, Pianelle, Brolio, Gaiole, Vertine. Radda.
- 1.00pm - Lunch on the road
- 3.00pm - Back to the villa for relaxing afternoon
- 6.00pm - Cooking Class, Demonstration and little work, learning basic of cooking.
- 8.30pm - Dinner will be served
- 8.00am - Breakfast and Day Briefing
- 9.00am - Departure for Buonconvento
- 10.00am - Start Ride, 50 miles, Queen stage, through Val d’Orcia, all rolling hills, riding through the town of San Quirico, Montepulciano, Pienza (capital of the Pecorino).
- Lunch in Montepulciano
- 4.00pm - Arriving at the Villa in Buonconvento
- 5.00pm - Arriving in Montalcino for visit of the town.
- 7.00pm - Aperitivo in downtown Montalcino and Dinner at “Le Loggie” restaurant.
Last day of Riding
- 8.00am - Breakfast and Day Briefing
- 9.00am - Start Ride, to Siena through some of the Strade Bianche routes.
- 12.00 - Lunch in Siena at " Le Telline Trattoria"
- 4.00pm - Arriving at the Villa
- 7.30pm - Aperitivo
- 8.00 - Dinner at the "La Bettola dell'Eroico" for the Menu Eroico.
- 9.00am - Breakfast
- 11.00am - Departure for Florence Airport or sooner based on needs
- 12.00pm - Arriving at the Airport.
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.
