May 9 - 16, 2020

Cycling in Tuscany is the perfect blend of stunning landscapes, twisting roads, legendary food and wine. Pre-Etruscan hilltop towns dot the countryside linked with winding and hilly roads that wander through vineyards and agricultural fields.  This will be Wild Rock's 8th trip to Tuscany and we have it down to a fine art. 

Rider Type: Intermediate and Advanced




Friday, May 8th (Late afternoon / evening)

Arrival and first night of accommodations: Saturday, May 9th


Saturday, May 16th

Last night of accommodations: Friday, May 16th


  • Schedule your flight to arrive at the Rome Airport (FCO) in the morning or early afternoon of Saturday May 9th to meet your transfer to the hotel. This will likely mean that your flight will depart from Toronto on the evening of Friday May 8th.

  • If you choose to arrive in Italy early or stay a bit later, that’s great! We are happy to arrange extended accommodations for you.

  • If you’d prefer NOT to fly with your bike, we can arrange to have a performance rental bike for ready for you when you arrive.


This is a sample itinerary that will give you an idea of the type of trip that you're in for!

One of the benefits of travelling with Wild Rock in Tuscany is that we can be, and are, very flexible with our itineraries. Considering the weather and group dynamics, we often make changes to ensure that you have the best trip possible. In the lead-up to the trip, you can expect to receive more detailed information and maps for some of our amazing rides!

DAY 1 - 3

Our first 4 nights are spent in CastelVecchi. This “Borgo” or small walled enclave sits atop a small hill surrounded by its own vineyards near the town of Radda in Chianti. Our rooms are in ancient stone buildings and offer fantastic views. Handily they also sit next to the wine cellar first started over one thousand years ago!

The 4 days we will spend riding around Radda in Chianti offer manageable but challenging climbs and endless great views of vineyards, forest and hillside villages. We offer 2 groups that do similar but not identical routes, so if you want to attack many hills at a strong pace we will have a group for you. Likewise if you wish to tackle a smaller number of climbs we will have a group for you.

Lunches on the road are an intricate part of the experience as they allow us to once again immerse ourselves in legendary Tuscan cuisine and espresso. Lunches are to be savored and not wolfed down like a Clif bar!

In the evening CastelVecchi hosts us in their own private restaurant where we can sample their wines over 4 course meals. Numerous hours are spent enjoying the quiet and spectacular sunset vistas.

DAY 4 - 6

Mid-stay we transfer to the walled city of San Gimignano. Settled in the 3rd century BC, San Gimignano is one of the finest walled hilltop villages in Tuscany. Its skyline is dotted with stone towers and its cobbled streets are pedestrian only. We stay in the heart of the town at Hotel Bel Soggiorno, which features spectacular sea views. Our breakfast table has breathtaking views of the countryside while our front door opens onto the cobbled interior streets filled with cafes, shops and restaurants.

During the day San Gimignano can feel stuffed with tourists as they are dropped off from nearby Siena and Firenze. It is fortunate for us we will be out riding during these hours and when we return home the hoard of tourists are gone and we have the town almost to ourselves (due to the fact there are so few hotel rooms in the town).

The riding around San Gimignano is incredible. Eerily quiet roads that snake through the hills, fields and towns. It feels like the immaculate tarmac has been laid solely for us sometimes as there is little traffic once you are 5km from San Gimignano. In our 2.5 days of riding in the area we will also have lunch in Volterra; another classic walled village.

Our dinners will be taken in 3 different classic Tuscan restaurants. The food and drink really must be experienced in your lifetime and tastes doubly good after a fine day of cycling.

DAY 7 - 8

Our final night is spent in a Rome airport hotel. Many of our guests choose to extend their stay in Rome. This extraordinary city can make a great 2-3 day extension to this cycling trip.




  • 7 nights of accommodation.

  • Breakfasts and dinners. 

  • Shuttle between the hotel and the airport on travel days.

  • Daily guide support.

  • Routes selected, designed and guided by Wild Rock Travel guides.


  • Airfare to and from Rome, Italy.

  • Alcohol.

  • Lunches - we believe that eating lunches out at cafés and restaurants during a ride is a unique and important part of the European cycling experience. Bring some euros to buy your café au lait and a lunch that suits your fancy.

  • Cycling specific nutrition - we will provide some fruit and snacks for riding, however we recommend that you bring the gels and drink or electrolyte mix that you’re used to using at home.

  • Additional food between meals.

  • Rental bike (if not travelling with personal bicycle).

  • Transportation to and from Pearson International.


Rental bikes are available for $290CAN for Bianchi aluminum/carbon bikes and $380CAN for Pinarello.