Bike Tuscany
-
Details & Cost
Dates: June 29-July 5th, 2026 (6 nights, 7 days)
Location: Tuscany - Radda in Chianti & Montalcino.
Cost: $4,450.00 pp twin-share; Bike Hire: $570.00 (includes helmet, lock, water bottle and set-up).
$200 supplement for bike cases/bags if taking own bikeInclusions: 6 nights accommodation, guided rides, bus transfers, support bus, 2 x dinners, 1 x lunch, breakfast daily, welcome drinks, Solo Bike Cycle Jersey, Solo Bike host 24/7.
Online Booking Form
Single supplement available on request. -
Radda in Chianti
Radda in Chianti is a medieval town nestled in the hills between Florence and Siena. It’s known for its narrow cobblestone streets, stone buildings, and panoramic views of the Chianti countryside. The town has preserved its old-world charm, making it a perfect destination for those looking to experience authentic Tuscany.
Surrounded by rolling hills, olive groves, and forests, Radda is also a great base for cycling. There are trails that wind through the countryside, offering stunning views and peaceful landscapes perfect for our rides.
-
Montalcino
Montalcino is a picture postcard hilltop town located in the Siena province.
It is famous for its Brunello di Montalcino, a red DOCG Italian wine produced in the vineyards surrounding the town.
We are situated in the perfect location, overlooking the stunning Tuscan countryside with ideal access to the rolling hills that make this area such a perfect cycling location.
TRIP ITINERARY
Join us for a week of cycling splendour in central Tuscany. Our 7 day/ 6-night itinerary we stay in Italy’s most famous wine location, the medieval hilltop town of Montalcino, and the beautiful countryside of Radda in Chianti.
Both locations offer Italy’s most idyllic countryside roads for cycling, as well as slow cultural immersion making this itinerary the perfect cycling holiday.
ITINERARY
29th June: Arrival Radda in Chianti
Group pick up from Siena station and transfer to Radda in Chianti, renowned for its stunning landscapes, historic architecture, and world-class wineries. Here we stay in 4-star spa hotel, Relais Vignale & SPA.
Bike set-ups are followed by welcoming drinks and evening dinner together in hotel.
Meals: Dinner and Welcome Drinks
30th June: Southern Chianti loop ride (approx. 80km/ hilly)
Our first ride in the Chianti focuses on the beautiful rustic countryside of Southern Chianti. Our loop ride from our hotel in Radda takes us via the charming village of San Gusme and peaceful roads and atmosphere of Castelnuovo Berardenga. In fact, Castelnuovo is a designated Città Slow (Slow town) for its authentic Tuscan style of slow living.
Meals: Breakfast
1st July: Northern Chianti loop ride (approx. 80km/ hilly)
Today’s ride takes us on a discovery excursion of Chianti’s northern terrain. This loop ride from our hotel in Radda takes us via the sleepy hilltop villages of Montefiorelle and Panzano, and ancient Florentine chianti market town of Greve. The area is renowned as a gastronomic hotspot of Tuscany, as well as for its rural beauty so idyllic for cycling.
Meals: Breakfast
2nd July: Montalcino (approx. 90km/ hilly)
We leave Chianti by bike for the hilltop town of Montalcino, home of Italy’s World-famous red wine, ‘Brunello’. Here we stay 3 nights in Hotel Vecchia Oliviera, formally an oil mill, perched spectacularly on Montalcino cliff-face overlooking the UNESCO World heritage listed landscapes of the Val d’Orcia.
Meals: Breakfast
3rd July: Val’ d’Orcia Loop Ride (75km)
Our final day of riding explores the roads of the UNESCO World Heritage listed landscapes of the Val d’Orcia. Highlight on route is the picture post-card town of Pienza, a renaissance hill-top town that sits like a balcony within the heart of the Val d’Orcia. Here the views over the countryside are extraordinary, as is the riding within this most beautiful region of Italy.
Lunch at winery Ciacci Piccolomini d’Aragona where we will enjoy wine tasting and a typical Tuscan fare.
Meals: Breakfast & Lunch
4th July: Mont Amiata: 110km or 55km
Magnificent day of riding today as we explore the nearby mountain of Mont Amiata which forms a natural barrier wall between Tuscany and Lazio (Rome). Riding to just under 2000m, Mont Amiata offers to most quiet and peaceful of riding roads, combined with sweeping countryside views of rare beauty across southern Tuscany.
There will be an option for a shorter ride with a bus to return to Montalcino
Meals: Breakfast and Dinner
5th July: End of Trip
Transfer return to Siena station.
Check out all our trip pics on Facebook
Accommodation
Radda in Chianti - 4 star Relais Vignale & SPA
The Relais Vignale & Spa is an 18th century manor house, recently renovated respecting the original and traditional architecture, in a warm and elegant setting.
The Relais is an authentic gem in the heart of Chiantishire, one of the most beautiful and renowned cultural areas in Italy and the world.
Montalcino - 3 Star Hotel Vecchia Oliviera
Hotel Vecchia Oliviera is located in the historic centre of Montalcino and stands next to Porta Cerbaia, one of the six ancient gates to the city of Montalcino. Montalcino is the home of the Brunello wine and a favourite town of many of our guests.
What our guests are saying…
-
The tour operated by Darren and Kerri is once in a lifetime for me and I am grateful for the opportunity to participate with the other riders. I thoroughly enjoyed my self with the challenges that were put to me and I will encourage other members of my cycling club and well as my wide range cycling friends who I feel should consider the Solo Bike Tour.
Jeff Hibberd
-
It was an absolutely terrific trip. So well planned and executed. Your team are first rate. I will (of course) be recommending you highly
Jeremy Shapiro (4 trips with SB)
-
”Out riding today, the second ride since returning home, we were discussing the trip and again commenting on how fortunate we were to have toured with the Solo Bike team, the quality of our fellow participants and new friendships we have made. Thanks”.
Brad & Kate Sewell (4 trips with SB)
