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Tuscan Bicycle Tour BT4-6

Bicycle tour in Tuscany and Umbria
Views of Umbria while on a bicycle tour
Taking a break while bike touring in Italy
Delicious food while bike touring in Italy
Tuscany and Umbria bicycle tour
Overview

Highlights

  • GO savor world-famous wine, scrumptious local cheese and a wide variety of delicious local products
  • GO cycle the UNESCO World Heritage rolling hills of Tuscany, meandering through vineyards and authentic Tuscan villages
  • GO back in time and discover medieval villages sorrounded by ancient city walls

Experience some of the most iconic hilltop towns and vineyard views of Tuscany, while soaking in the true and authentic Tuscany, as you cycle through some of our favorite authentically undiscovered villages of the region. You’ll start from Cortona, Hollywood’s favorite Tuscan hilltop village, thanks to the movie, Under the Tuscan Sun.  From Cortona, you will ride the Orcia Valley, enjoy the Unesco hills of Siena, and soak in the picturesque medieval hilltop towns of Montalcino and Montepulciano. The route ends in Siena, the bustling hub of Tuscany. Still surrounded by its ancient city wall, Siena is full of cultural and culinary treasures, just waiting to be discovered.
 
Along the way, there will be endless opportunities to indulge in the many gastronomical delights: olive oil, truffles, pecorino cheeses, pici and a variety of handmade pastas, fresh local produce and more as you explore historical towns and villages, some touristy and some authentically local.  You’ll find dozens of wine cellars with free tastings of the most incredible wines in the world. 
 
From the saddle, you’ll collect impressions of barren hills crowned by ancient manor houses, winding country roads lined with cypress trees, grazing sheep, and Tuscany’s famous luscious vineyards. Bike along cypress-lined rolling hills peppered with poppies and sprinkled with sunflowers.
 

This biking tour is a trip through time, from the Medieval hilltowns to Renaissance basilicas. It also offers a various landscape, from the vineyard covered hills of Chianti and Brunello to the barren geometrical cypress-crested mounds of the “Crete.” Every day a new adventure, a new discovery.

The Tuscan Bicycle Tour follows mostly paved roads with light traffic and thanks to luggage transportation, it is appropriate for both road and touring bicycles. The hilly terrain makes for an invigorating challenge. This entire tour travels on roads, most of them lightly driven.
Due to the hilly terrain, and the end-of-the-day ascent required to reach the hill-top towns, we recommend indulging in an eBike rental. You can see more about bicycle rentals on the Add-ons tab.

We partner with local bicycle tour experts in Italy to provide you with this tour.


Length        6 days

Season        March to June / September to November

Airport       Rome, Italy

Physical Condition
eBike

Technical Difficulty

Read more about difficulty ratings

Responsible Travel Score:
12/15 Responsible Travel Leader
(detailed summary available in Tour Documents)

Itinerary
Map
Skills Required
Tour Documents
Pricing
Add-ons
Accommodation and Meals
Season and Timing

We accept bookings up to 21 days prior to the start date of the tour

Only 20% payment due at the time of booking!

Current Availability

Updated October 30th, 2025

We are currently accepting bookings for 2026 itineraries.

You can book the tour online by following the green button “GO Book the Tour.”  

 

Useful Links

Booking Process

  1. Initiate the booking process by selecting the green button labeled, GO Book the Tour
  2. Complete the fields in the booking process and continue on to process the deposit (usually 20%, sometimes 30%) via Paypal (Paypal account not needed)
  3. We'll start checking availability and working on your bookings. As long as there is availability, we will book the accommodations and send you your eGuidebook within 21 days of the booking (this may take longer for custom tours and last-minute tours). This will include GPS waypoints of the accommodations and will be in a format that can be saved on your smartphone for convenient use on the tour. If any changes need to be made during the tour, there will be a phone number available to you during the tour, although additional charges may apply

If there are any issues with availability, we will contact you and work with you to find an alternative solution. If we are unable to find one, we will refund the deposit in full.

The remaining balance for the tour is due 30 days prior to the first date of the tour.

Group Discount

Only one discount will be applied per tour participant. Discounts are only applicable to tours. Discounts are not applicable to fees or additional services, such as Airport to Airport Packages or bicycle rentals.

Groups of 6 or more: 15% discount for all participants & customize an existing tour without Customization Fees

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