TUSCANY - A fantastic journey

Duration: 7 Days
Languages: English
Scale: 2 - 7 people
Categories: Bike Tours
This road bike tour in Tuscany will take you through some of the most picturesque landscapes in the World, immersed in history with unique scenery full of surprises, where you can discover the real Italy.

Duration: 7 days (6 nights)

People: maximum 7

Daily km: 65/75 (total 335 km)

Diffuculty: MEDIUM

Departure Dates 2021April 18th, May 2nd, May 30th, June 13th, June 27th, September 12th, September 26th, October 10th 

Day 1: Arrival in Siena, welcome from the staff.
Presentation of the trip, assembly and preparation of bikes. Welcome drink. Dinner Monteriggioni Castle. Overnight at Sangallo Park Hotel

Day 2Siena and Chianti Loop. 70km
Our first contact with this extraordinary region takes place in the Chianti Hills area. This area, famous all over the world, gives the name to the excellent Chianti wine. We’ll start our cycling day directly from our Hotel in Siena and heading to Gaiole in Chianti, we’ll ride through these rolling hills, surrounded by vineyards deep in an enchanting landscape. Once we arrive in Radda in Chianti we’ll stop for a cappuccino and cornetto in its  magnificent old square. After our stop, we’ll keep on riding up and down, enjoying breathtaking views: vineyards and wild areas. going through historic villages. Getting to the Hotel, we can wind down in his swimming pool and get ready for our delicious dinner in Siena. Overnight at Sangallo Park Hotel

Day 3Siena – Montalcino 75km
After an excellent breakfast, departure towards Monteroni D’Arbia on quieter secondary roads, through the magnificent Val d’Arbia. We will then continue towards Asciano, with its splendid Monte Oliveto Maggiore abbey. Riding up and down between hills and cypress trees you will arrive at Buonconvento, in the Ombrone valley. The final stretch of the day’s ride takes us to our destination today: Montalcino. This town is well-known for the production of the famous Brunello wine, which you may be interested to know is never sold less than five years after the grape harvest, and becomes “Reserve” after at least six years . Welcoming accommodation and an excellent dinner of local food and fine wine bring this first day by bike to an end. Overnight at Hotel dei Capitani

Day 4Montalcino Loop 68 km
A new unforgettable day is waiting for us. Today we’ll get in touch with the unique Val D’Orcia,riding on peaceful back roads. We’ll start our day dealing with the descent from Montlcino to Torrenieri, then we ride with continuous up and down through ancient villages, where we’ll have our inevitable cappuccino and espresso. Then, we must absolutely visit the splendid San Quirico d’Orcia, where we can have a lunch in a typical “trattoria” to recovery energy for taking on the demanding Montalcino ascent. This ascent is 10 km long with a difference in altitude of 500m.
An exclusive dinner in this fairy-tale village will close our fourth day. Overnight at Hotel dei Capitani

Day 5Montalcino – Acquapendente 72km
Another superb day through villages surrounded by breathtaking nature. San Quirico d’Orcia is the first village we encounter, the spa in its hamlet Bagno Vignoni is famous. Radicofani, a wonderful village dominated by a castle, is waiting for us along the way. Finally, we ride into the Lazio region at Acquapendente, where we will be justly rewarded for our efforts with a visit of the historical centre and an excellent dinner. Overnight at Sant Apollinare Farmhouse

Day 6: Acquapendente – Lake Bolsena 65 km
A change of scenery is the main feature of today’s ride: we ride back, briefly, into the Tuscany region and arrive in Pitigliano, with its characteristic historical center called “Little Jerusalem” because of the presence of an ancient Jewish community. After leaving Pitigliano we head for Lake Bolsena, a destination that coincides with our return to the Lazio region, Civita di Bagnoregio is waiting for us. Here, a very different landscape will provide the ideal setting for an evening in good company and a delicious dinner. Overnight at Hotel Royal

Day 7: Breakfast and transfer to Siena

EXTRAS: Single room option 350€, Rent of carbon racing bike 190€, rent of e-roadbike 440€.

Booking modifications and or amendments must be sent to and confirmed by My Trip To Italia.

  1. My Trip To Italia does not charge a fee to amend or change the dates or times of an existing booking. Amendments or changes must be received no later than 7 days before the date of the tour. My Trip To Italia does not guarantee changes/amendements will be accepted.
  2. If you request a date/time change we will try to adjust your booking to your request at our best possible however My Trip To Italia cannot guarantee changes to bookings since these are subject only to availability.


  • Full payment by credit card is required to validate a reservation.
  • Cancellation up to 30 days results in a cancellation fee of 20% of the total amount paid
  • Cancellations must be received in writing via e-mail to: This email address is being protected from spambots. You need JavaScript enabled to view it.
  • Museum tickets are non refundable in all cases
  • No refund for cancellations from 29 days to no show of the date of the tour/experience
  • There is no refund for No Show to any of the booked tours/experiences.


You will receive a voucher for each tour booked. You must provide the voucher at the start of your tour. Voucher/s are issued in client name and are not transferable. On the voucher meeting point and time will be specified. If for any reason client is delayed or does not see the supplier at the meeting point, he/she must immediately advise by calling the number on the voucher for assistance.

From / per person

€ 2,790.00
It is not available at this moment
Departs at
7 participants left
Important information
- Minibus assistance - Taxes - Luggage transfer - 6 nights accommodation - 6 dinners - 6 breakfasts - Technical bike guide - Technical assistance - Technical Bike Shirt - Transfer station/hotel
- tips - laundry - service - drinks at dinner - medical insurance - lunches (everything is not explicitly written in this page)

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