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Italy · 14 retreats
Compare 14 cycling holidays in Italy. Prices from €632. Expert-reviewed retreats with real photos, itineraries and verified availability.
The top-ranked cycling holidays in Italy on Book Fitness Retreats are 5 Day Island Reset & Transformation, Women's Road Cycling Camp and Guided Road Cycling Training Camp. There are 11 to compare, with prices from €632 to €4,698 per person, stays of 3 to 14 days and dates in every month of the coming year.
| Retreats listed | 11 |
|---|---|
| Price from | €632 per person |
| Price up to | €4,698 per person |
| Length of stay | 3 to 14 days |
| Months with dates | Every month |
A cycling holiday in Italy costs from €632 to €4,698 per person on Book Fitness Retreats, across 11 listings. That covers stays of 3 to 14 days. The price depends on how long you stay and the room you choose.
All year: the cycling holidays in Italy listed on Book Fitness Retreats have dates in every month of the coming year.
Figures from the live listings on Book Fitness Retreats, last updated .
Italy gives cyclists something few places can match: quiet roads that wind between vineyards and hilltop towns, with a farmhouse or a castle to return to at the end of the day. This page has two cycling holidays, both in Tuscany, and each offers a different way to spend your time in the saddle.
The longer of the two is an eight-day gravel and road cycling week based at Palazzo a Merse, a farmhouse B&B near Siena where you stay all week. The riding takes in the white gravel roads of the Strade Bianche, the Chianti countryside and the region's hilltop towns. You arrive on Saturday 13 June, ideally before noon. A group transfer collects you from Florence airport (FLR) and takes you out to the farmhouse, and the first afternoon is left free for unpacking and settling in.
If you would prefer a shorter break, the five-day cycling retreat at Castello di Santa Cristina uses a historic 17th-century castle in the Province of Grosseto as its base for exploring scenic cycling routes across Tuscany.
Between them, these holidays suit riders who want to see Tuscany on two wheels. You can choose a full week mixing gravel and road riding from a farmhouse near Siena, or a few days of cycling from a castle in Grosseto. Prices on this page run from 699 USD for the five-day retreat to 4195 USD for the eight-day week.
Prices on this page range from 699 USD to 4195 USD. The five-day retreat at Castello di Santa Cristina starts from 699 USD. The eight-day Tuscany gravel and road cycling week near Siena starts from 4195 USD.
There are two lengths on this page. The retreat at Castello di Santa Cristina lasts five days, and the Tuscany gravel and road cycling week lasts eight days.
Both holidays on this page are in Tuscany. The eight-day week is based at Palazzo a Merse, a farmhouse near Siena. The five-day retreat is based at Castello di Santa Cristina in the Province of Grosseto.
The eight-day week combines gravel and road cycling, taking in the Strade Bianche, the Chianti countryside and Tuscany's hilltop towns. The five-day retreat at Castello di Santa Cristina uses the castle as a base for exploring scenic cycling routes in the area.
On the eight-day week you stay all week at Palazzo a Merse, a farmhouse B&B near Siena. The five-day retreat is based at Castello di Santa Cristina, a historic 17th-century castle in the Province of Grosseto.
For the eight-day week, a group transfer collects you from Florence airport (FLR) and takes you to the farmhouse at Palazzo a Merse. You should aim to arrive before noon on the first day.
You arrive on Saturday 13 June, ideally before noon. The first afternoon is set aside for unpacking and settling in at the farmhouse before the riding begins.