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. |
DATES: September 18 - 25, 2023
START/END: Florence/Florence NIGHTS OF LODGING: 7 DAYS OF CYCLING: 5 TOTAL CYCLING DISTANCE: 220 miles DIFFICULTY LEVEL: Intermediate PRICE: $3400 per person |
itinerary |
cuisine |
lodging |
preparation |
Itinerary
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Day 1 - Mon 18th
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Day 2 - Tues 19th
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Day 3 - Wed 20th
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Day 4 - Thurs 21st
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Day 5 - Fri 22nd
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Day 6 - Sat 23rd
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Day 7 - Sun 24th
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Day 8 - Mon 25th
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- 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 Hotel
- 8.00am - Breakfast and Day Briefing
- 9.00am - Wheels up, First day of Tuscany Trail Gravel Experience,
- Pisa to Volterra, 55 miles, flat course for the first half, rolling for the remaining with final climb to Volterra, riding through the towns of Pontedera, Peccioli, Lajatico arriving in Volterra.
- Lunch on the road at local Trattoria
- 4.00pm - Arriving at the Hotel in Volterra
- 7.00pm - Aperitivo and Dinner at “La Mangiatoia” in downtown.
- 8.00am - Breakfast and Day Briefing
- 9.00am - Start Ride, Volterra to Colle di Val d’Elsa, 50 miles, decent to start the ride, main climb after, rolling hills or the remaining of the route, Riding through the towns of Pignano, Gambassi Terme, Certaldo, San Gimignano
- Lunch in San Gimignano
- 4.00pm - Arriving at the Villa/Agriturismo in Colle di Val D’elsa
- 7.00pm - Aperitivo and Dinner at the Villa
- 8.00am - Breakfast and Day Briefing
- 9.00am - Start Ride, Colle di Val d’Elsa to Montalcino, 50 miles, all rolling hills ride with final climb to Montalcino, main climb after, rolling hills or the remaining of the route, Riding through the towns of Monteriggioni, Siena, Bonconvento.
- Espresso in Piazza del Campo in Siena, Picnic Lunch along the way.
- 4.00pm - Arriving at the Hotel/Agriturismo in Montalcino
- 7.00pm - Aperitivo in downtown Montalcino and Dinner at “Le Loggie” restaurant.
REST DAY
- 8.30am - Breakfast
- 11.00am - Visit at Ciacci D’Aragona Winery, Brunello Tasting and Lunch
- 2.00pm - Departure for Siena
- 3.00pm - Arriving in Siena
- Afternoon visit of Downtown Siena
- Date Dinner Night
- 9.00pm - Drive back to the Montalcino
- 8.00am - Breakfast and Day Briefing
- 9.00am - Start Ride, Montalcino to Buonconvento, 55 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
- 7.00pm - Aperitivo
- Dinner at the Villa
Last day of Riding
- 8.00am - Breakfast and Day Briefing
- 9.00am - Start Ride, Buonconvento to Gaiole (home of the Eroica) 47 miles, continuing into Val d’Orcia, arriving in Chianti, riding through the towns of Asciano, Castelnuovo di Berardenga, Castello di Brolio.
- Lunch in Castelnuovo di Berardenga at “Le Due Sorelle” Trattoria
- 4.00pm - Arriving at the Villa in Gaiole
- 7.00pm - Aperitivo
- Dinner at the Villa
- 9.00am - Breakfast
- 11.00am - Departure for Panzano in Chianti, stop for Espresso in Radda in Chianti
- 1.00pm - Lunch at “Solo la Ciccia” in Panzano home of the “Butcher” Dario Cecchini.
- 4.00pm - Arriving in Florence
- Ending of an amazing week of gravel riding, food, wine and spectacular endless sight seen.
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.