Discover Tuscany’s Hidden Roads
tour overview
Summary
From Siena to Bologna
Start/End
Dates 18th May – 24th May
Arrival/Departure
Venice / Bologna / Florence
Duration
7 Days / 5 Rides
tour overview
Tuscany is a land where cycling and culture come together in perfect harmony. Tuscany has always been deeply connected to Italian cycling, from the legendary white gravel roads to the champions who made these hills their training ground, and every ride here feels like a journey into the very soul of the sport.
This 7-day tour takes you through some of Tuscany’s most captivating landscapes, including the Siena and Chianti region, the rolling hills of the Val d’Orcia and Crete Senesi, and the classic white roads made famous by Strade Bianche and L’Eroica. The journey also includes the Tuscan coastline, the Versilia, where we’ll experience the Giro d’Italia live, positioning ourselves along the individual time trial between Viareggio and Massa, the only chance to watch the best riders race against the clock during the race.
From Chianti’s vineyards to tuscany’s iconic strade bianche, ride where legends trained and the spirit of cycling was born
Your experience will be a balance of road and gravel riding, combining quiet country lanes, rolling hills, coastal panoramas, and unforgettable white roads. Along the way, you’ll also savor the region’s deep wine tradition, enjoying both the elegance of Chianti and the Montepulciano to name two, paired with the unique flavors of Tuscan cuisine, from rustic breads, the handmade pasta and the Bistecca Fiorentina, each taste a reflection of the land that you’ll ride through.
The tour concludes in Bologna, adding a new cultural and cycling dimension to the experience. Here, we’ll explore the surrounding hills and tackle the famous San Luca climb and its portici, before enjoying time in one of Italy’s great food cities.
Inclusions & Details
Accommodation
Your home for the week will be carefully selected 3 and 4-star cycling-friendly hotels, chosen for comfort, location, and hospitality. All stays are in twin share rooms with private bathrooms, with the option of single occupancy available on request. Where possible, a cycling kit laundry service is included, so you can focus on the rides without worrying about the small details.
Ride Support
Every ride is fully supported by our experienced guides, both on and off the bike. We keep our groups small, with a maximum of 12 guests including guides, to ensure a personal and friendly atmosphere. One guide will ride alongside you, while another follows in the support van carrying daypacks, spare parts, hydration, and ride snacks. Mechanical support is always close at hand, and we’ll provide downloadable GPS routes with assistance for setting up your device.
Transfers to and from Airport
From the moment you arrive in Italy, we’ll take care of all transfers. Pick-up and drop-off services are arranged from airports and agreed locations at the start and end of the tour. We’ll also transport all baggage and bikes, as well as handle internal transfers between daily destinations, regions, and hotels, so your focus remains on enjoying the ride.
Bike rental
To make your trip easier, we offer high-quality road bike rentals at a great weekly rate, so, you can travel light without worrying about transporting your own bike. Tell us if it is your preference. As part of the experience, a gravel bike rental is included for one full-day adventure, giving you the chance to discover the iconic white roads of Tuscany in true local style.
Mangia e bevi
Cycling in Italy is as much about food as it is about the ride. During the tour, daily breakfast is included, giving you the energy to start each day on the bike. Lunches and dinners are not included, so we can remain flexible and choose the best local trattorie and restaurants along the way, discovering authentic Tuscan cuisine and world-famous wines. This also gives you the freedom to enjoy a relaxing evening at your own pace if you prefer to explore the town on your own. On the bike, nutrition is provided, like bars, gels, and drinks, and of course, the essential coffee and pastry stops are on us.
InGiro cycling kit
Each tour features a custom InGiro cycling kit, designed to capture the spirit of the journey. You’ll receive a premium jersey and bib shorts, along with a special welcome pack prepared with our compliments. It’s both a keepsake and a practical companion, something you’ll wear proudly on the roads of Italy and beyond.
WHAT’S INCLUDED
- Accomodation
- Ride support
- Transfer
- Meals, see details
- Bike nutrition
- InGiro cycling kit
WHAT’S NOT INCLUDED
- Bike hire
- Airfare
- Travel and international medical insurance
- Guide gratuities
KEY DETAILS
Arrivals : Our meeting point will be Venice Airport or Venice-Mestre train station on 25 May 2026, to join the scheduled group transfer departing around 2.00 PM (exact time to be confirmed based on everyone’s travel arrangements).
If you plan to arrive before the 25th, we’re happy to recommend nearby accommodation, just let us know.
Departures : Please share your travel plans after the cycling tour, and we’ll arrange your transfer to Venice Airport or Venice-Mestre train station for your departure.
Private transfers outside the scheduled group transfers at the beginning or end of the tour can be arranged at an additional cost.
Contact
Thinking about joining one of InGiro’s tours and want to know more?
Or planning to travel to Italy on different period and interested in organizing a private cycling experience?
We’d love to hear from you, tell us your plans, and we’ll help you create your perfect Italian ride.
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