Tuscany is known for its Etruscan villages perched atop of hills, its Renaissance masterpieces and its incredible history. Yet, the Tuscany you discover by bike is even more amazing. It is a land with a unique countryside. Cypress-lined roads, endless acres of vineyards and rolling hills is only the beginning. Don’t wait and come discover the rest by yourself on a cycling vacation of a lifetime.

Dates: Jun. 25 | Jul. 2 | Jul. 9 | Jul. 16 | Jul. 23 | Jul. 30 | Aug. 6 | Aug. 13 | Aug. 20 | Aug. 27 | Sep. 3 | Sep. 10 | Sep. 17 | Sep. 24 | Oct. 1 | Oct. 8 |

Trip Price:


Biking Level:


Hotel Style:


Trip Type:




6 Days / 5 Nights

Limited to:

14 Guests

Start / End:

Chiusi / Firenze


Bike Rental:


Trip Highlights

Day 1 – 2: Start your adventure at your hotel with a light Tuscan lunch. star Cycle by the perfect picture of an authentic Tuscany town, Montepulciano. star Join a winemaker for a tour and tasting of Vino Nobile. star Visit the town of Pienza and ride to Petroio and Castelmuzio.

Day 3: Cycle to Rocca d’Orcia, a little hamlet for lunch in town. star Relax at the spa where you can enjoy 360-degree view of the surrounding landscape. star Visit the abbaye of Sant Antimo and listen to the resident monks engaging in a beautiful round of Gregorian chanting.

Day 4 – 5: Cycle uphill toward the town of Montalcino. star Pedal through the beautiful terrain of Crete Senese, a landscape that seems almost lunar. star Explore Siena and its famous Piazza del Campo. star Ride your way over a chain of beautiful rolling hills, arriving in chianti. star Bring your vacation to a fitting close with dinner at the hotel’s gourmet restaurant.

Hotels you will be Staying at During your Cycling Vacation

Villa Cicolina

4 Star Hotel
(2 Nights)

Castello di Velona

5 Star Hotel
(1 Night)

Borgo San Felice

5 Star Hotel
(2 Nights)

Included / Not Included



Hybrid bicycle, DIGnGO water bottle, helmet, Garmin GPS and saddle bag.



All breakfasts, 1 lunch and 4 dinners. Your leaders have recommendations for the meals on your own.


Snacks & Refreshments

During the day, your leaders are along your bicycle route with water, M&M’s, dry fruits etc..


One or More Leaders

1 leader for every 5 guests. With a minimum of 2 leaders on all our trips, you’re guaranteed a great tour.



Guided tours of wineries and historic sites with local guides. See the detailed itinerary for a list of activities.


Van Support

A leader is in the van, sweeping the route and making sure you have enough water, giving you a boost up a hill or fixing a flat.


Luggage Transfer

Your luggage is delivered to your room before your arrival at the next hotel.



Any type of transportation to and from the pick up/drop off locations.


Pre/Post Trip Lodging

Hotels or house rentals before and after the trip.


Personal Expenses

Minibar, massages, laundry, non scheduled activities, etc.


Alcoholic Beverages

All alcoholic drinks are at your own expense.


Gratuites for your Leaders

Industry standard is 5% of the trip price per team of leaders.

Read More About the Trip

The itinerary has detailed information about activities, what’s included, gratuities, etc…

Download Itinerary