Itinerary
- Day 1
Chianti
You'll arrive at Relais Il Vignale and get settled in, then meet up with the tour team. A short warm-up ride gets everyone comfortable on their bikes and checks that the equipment's working properly before the week really starts. Later this evening, the hotel's chef hosts a welcome dinner so you can meet fellow riders and get ready for tomorrow.
- Meals
- Lunch (Light lunch upon arrival at the hotel), Dinner (Welcome evening meal hosted by the hotel's excellent chef)
Included Activities
- Warm-up ride in Chianti (19.3 km, 306m elevation gain)
Landmarks Chianti - Day 2
Greve to Volpaia
Heading out to Greve this morning, you'll see the region's architectural heritage while riding through Tuscan gravel roads and learning about local wines. Lunch happens in Volpaia, a fortified village with hidden wine cellars tucked throughout. You'll stop at a Chianti vineyard for a wine tasting in the afternoon, then head back to town for dinner.
- Meals
- Breakfast, Lunch (Lunch en route), Dinner (Evening meal in town)
Included Activities
- Ride to Greve and Volpaia (66.9 km, 1655m elevation gain)
- Wine tasting in Chianti vineyard
Landmarks Greve in Chianti Volpaia - Day 3
Gaiole in Chianti
The ride south to Gaiole takes you through landscape shaped by centuries of regional battles and conflicts. You'll spot watchtowers scattered across the hills, many of which are open to explore. After cycling around, the evening is yours to spend however you like around town.
- Meals
- Breakfast, Lunch (Lunch en route)
Included Activities
- Ride to Gaiole in Chianti (69.9 km, 1216m elevation gain)
Optional Activities
- Visit watchtowers in Gaiole
Landmarks Gaiole in Chianti - Day 4
Radda to Siena
Today's a longer ride from Radda down to Siena, passing through villages like Castelnuovo Berardenga with vineyards on both sides of the roads. You'll ride into town and settle at Villa Curina, where dinner at the hotel wraps up the day.
- Meals
- Breakfast, Lunch (Lunch en route), Dinner (Evening meal at the hotel)
Included Activities
- Ride from Radda to Siena via Castelnuovo Berardenga (74.2 km, 1671m elevation gain)
Landmarks Castelnuovo Berardenga Siena 
- Day 5
Siena to Bagno Vignoni
Cycling to Bagno Vignoni means riding through the UNESCO-protected Siena hills and passing the distinctive eroded landscapes of Crete Senesi. You'll travel through Asciano and San Giovanni d'Asso, stop for lunch in San Quirico, then finish at Osteria dell'Orcia where you'll stay the night.
- Meals
- Breakfast, Lunch (Lunch en route in San Quirico), Dinner (Evening meal at the hotel)
Included Activities
- Ride through Crete Senesi and Le Strade Bianche section (62 km, 1271m elevation gain)
- Pass through Asciano and San Giovanni d'Asso
Landmarks Crete Senesi Le Strade Bianche Asciano San Giovanni d'Asso San Quirico Bagno Vignoni 
- Day 6
Bagno Vignoni to Pienza or Montalcino
Your final ride offers two options: take the shorter route to Pienza if you want a more relaxed pace (it's famous for its Pecorino cheese), or go longer to Montalcino for wine lovers. Either way, you'll celebrate finishing the tour with a farewell dinner in the village.
- Meals
- Breakfast, Lunch (Lunch en route), Dinner (Farewell evening meal in the village)
Included Activities
- Ride to Pienza or Montalcino (83.1 km, 1976m elevation gain - long route option)
Optional Activities
- Short ride to Pienza (UNESCO site known for Pecorino cheese)
- Long ride to Montalcino (renowned for wine)
Landmarks Pienza Montalcino - Day 7
Departure
The tour wraps up today. Let the team know your travel plans and they'll handle any transfers or logistics you need for heading home.
- Meals
- Breakfast
Optional Activities
- Arrange transfers based on departure plans
