Itinerary
- Day 1
Radda in Chianti
You'll arrive in Chianti and get settled at Relais Vignale Hotel. After checking in, there's a short warm-up ride to shake out any travel stiffness and get familiar with the bikes and roads. Light lunch happens when you get back, then you have time to rest before dinner at the hotel. It's a relaxed first day to adjust to the region and the pace of the week.
- Meals
- Lunch (Light lunch upon arrival), Dinner (Evening meal at the hotel)
Included Activities
- Warm up ride in Chianti region
Landmarks/POIs Chianti Region - Day 2
Radda in Chianti
This morning you'll head out toward the village of Greve, riding through classic Tuscan terrain with rolling hills that'll warm up your legs nicely. The route is about 70% paved and 30% gravel, so you'll get a good feel for the roads here. Along the way you'll pass through some charming spots and see the architectural and culinary character that defines this part of Tuscany. By evening, there's a wine tasting at a seasonal wine bar to celebrate finishing the ride, followed by dinner in town.
- Meals
- Breakfast, Lunch (Lunch en route), Dinner (Evening meal in town)
Included Activities
- Homage to the Chianti Wine Region cycling route (66.9 km, 1665 m elevation)
- Wine tasting at seasonal wine bar
- Greve village exploration
Landmarks/POIs Greve - Day 3
Radda in Chianti to Siena
Today is a longer route from Radda heading toward Siena. The elevation profile is more forgiving than yesterday, so it's less about grinding and more about enjoying the scenery. You'll ride past Colle val d'Elsa and Castello di Casole, both medieval villages worth seeing. There's time to walk around and check out the 14th-century architecture before heading to your hotel on Siena's outskirts. Dinner happens in Siena town, so you'll get an evening stroll through the city.
- Meals
- Breakfast, Lunch (Lunch en route), Dinner (Evening meal in Siena)
Included Activities
- Radda in Chianti to Siena cycling route (85.8 km, 906 m elevation)
- Colle val d'Elsa village visit
- Castello di Casole visit
- Siena medieval architecture exploration
Landmarks/POIs Colle val d'Elsa Castello di Casole Siena - Day 4
Siena
Today centers on watching the Pro Strade Bianche World Tour race. Depending on weather, you might ride part of their course in reverse and position yourself at the top of the first gravel climb to see them pass. After watching the pros do their thing, there's lunch at a local Tuscan restaurant nearby, then a short two-minute walk to the main square where you'll catch the race finale. It's a fun change of pace from riding hard yourself.
- Meals
- Breakfast, Lunch (Lunch in Siena at Tuscan restaurant), Dinner (Evening meal in Siena)
Included Activities
- Watch the World Tour Race cycling route (44.7 km, 781 m elevation)
- Pro race viewing at first gravel climb
- Gourmet lunch at Tuscan restaurant
- Race grand finale viewing in main square
Landmarks/POIs Siena - Day 5
Siena
This is race day for the Strade Bianca Gran Fondo. You'll start early and can pick either the long or medium route depending on your fitness level and how you're feeling. Both courses are challenging and designed to test your skills on gravel and paved sections. After finishing, you'll head to dinner in Siena's old town to celebrate completing the event and the whole trip.
- Meals
- Breakfast, Lunch (Lunch after the race), Dinner (Farewell evening meal)
Included Activities
- Gran Fondo race participation - long or medium route (138 km, 2093 m elevation)
- Lunch after the race
Landmarks/POIs Siena - Day 6
Departure
Time to head out. Let the tour organizers know when you're leaving and they'll arrange any transfers needed to get you to the airport or your next destination. It's a simple farewell morning after a week of riding through some of the nicest countryside in Italy.
- Meals
- Breakfast
