Photo ©giuliana mulas
Holiday packages
Full immersion in Val d'Orcia by bike
Escape in one the best of Tuscan hill towns, explore the countryside on two wheels and stay in a three-star superior hotel

We designed a short bike tour of 3 full days of cycling and 2 half days. Each day you'll have the possibility to choose between easy and short bike rides and more challenging ones.

Covered by vineyards and olive groves, the hills of Tuscany are perfect to be explored on two wheels. Pedal to lofty hill towns and follow sinuous country roads and cypress-lined lanes or quiet woodland. When you don’t pedal, discover the Renaissance art and architecture, medieval villages, and visit the winery and cellars: you will be in the heart of Brunello wine land.

Your Hotel Il Chiostro is hosted in a 15th-century convent in the center of Pienza, the “perfect town”, a remarkable example of Renaissance-era town planning, and it is also a paradise for food&wine lovers. Rebuilt between 1459 and 1462, it is a rare masterpiece: it was the brainstorm of Pope Pius II.

The second day you’ll ride through the villages of Castelmuzio and Petroio. You’ll arrive in Montepulciano, famous for the production of Vino Nobile. Here, you'll visit one of the oldest typical wine cellars in town, Cantina Ricci. Then, back to Pienza passing through Monticchiello, another hilltop village.

The third day, you’ll pass Bagno Vignoni, a thermal spa town, Castiglione d'Orcia and enjoy a long downhill to the monastery of Sant'Antimo. Soon you'll be in Montalcino, a fortified town, famous thanks to the production of red wines, such as the Brunello di Montalcino. Here you'll have the opportunity to visit the fortress and enjoy the view.

On day four, you’ll reach Siena. On the way you'll pass Monte Oliveto Maggiore monastery (make sure you stop here to visit and have lunch at the restaurant) and explore the area called Crete Senesi.

Prices starting from
Val d'Orcia
Pienza, SI, Italia
From 01 June 2021 to 31 October 2021
Tel.: 0578749983
Per prenotare
Prices include

Price per person euro 990 in double accommodation:

  • Four nights in excellent three-star superior hotel
  • Four breakfasts
  • Route notes, maps, elevation gain and city map
  • Sightseeing, restaurant and shopping suggestions in handbook
  • All baggage transfers
  • Pick-up of bikes and gear in Siena
  • Sales taxes
Supplemental charges

Lunches and dinners 

Meeting point

DAY 1: Welcome to Pienza! Meet and Greet, we'll fit your bikes and introduce you to the tour. Start with a loop to San Quirico to test the bicycle and the equipment! Stop in the village at Horti Leonini Garden. Total Distance 22 km

DAY 2: Montepulciano & Vino Nobile. Option A: Moderate to challenging Distance: 55 km / 34 miles; Option B: easy to moderate distance 35 km / 21 miles. Today you start with a downhill, arriving in Petroio and Castelmuzio, Montepulciano

DAY 3: Montalcino Brunello land. Easy to Moderate distance 34 km / 21 miles. Always downhill, passing Bagno Vignoni, Castiglione d'Orcia and Sant'Antimo, for lunch you can stay Montalcino, visit the fortress.

DAY 4: Siena, Etruscan and Palio race. moderate distance 50 km /32 miles. Arriving in Siena, along secondary roads. Passing Murlo, continue to Ville of Corsano and end up in Siena arch gate Porta San Marco.

Cancellation and no-show policies

If you decide to cancel your trip, the following fees apply and are due to Cicloposse at the time (prior to departure) we receive written notice (via confirmed e-mail) of your cancellation. No refunds are made for unused portions of the tour once it has began.

Cancellations made before 30 days prior to departure: booking deposit as processing fee
the booking deposit amount is changed due to Covid-19 situation: it will be euro 100 per person for tour booked for 2021

Cancellation made 30 days or less prior to departure:

In Self guided bike tour

  • 15-30 days= 25% of trip price
  • 0-15 days= 100% of trip price

In Guided bike tour

  • 15-30 days= 50% of trip price
  • 0-15 days= 100% of trip price

Cancellation and postponement due to COVID-19 conditions and concerns:

  • Up to 1 month before tour start: the booking deposit of euro 100 per person can be considered voucher and tour can be postponed
  • 30 to 15 days prior the departure the cost of tour can be kept on account for use for next 12 months
  • 15 to 0 days prior to departure 70 % of funds can be kept on account for use by for next 12 months

Please note, these terms may be amended to be more lenient depending on the COVID-19 global situation at the time of travel in 2021.

Read the cancellation policies
P.IVA: 00876140526
via I maggio 27
Tel: 0578749983