Day 1: Arrival in Pienza
Arrive in Pienza.  Please note that the closest station to Pienza is Chiusi—35 km from Pienza--on the Rome-Florence train line.  Alternatively, we can arrange a car transfer from Florence to Pienza.  After checking-in at your pre-arranged location in a former 15th century convent, you’ll meet our local representative who will outfit you with bikes and meticulously go over the itinerary.  Pienza is one of the four UNESCO World Heritage Sites you’ll encounter during your week-long history-laden cycling trip.

Day 2: Loop from Pienza to Pienza through Montepulciano - 50 km (31 miles)
You’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages…This where the English Patient was filmed.  Among the sites you’ll ride through is the hilltop village of Castelmuzio and Montepulciano, another hilltop village that will make a perfect lunch/wine stop (Montepulciano is home to the famous Vino Nobile di Montepulciano) before heading back to Pienza through Monticchiello…  another hilltop village!

Day 3: Pienza to Montalcino - 46 km (29 miles)
Today’s ride will take you to Bagno Vignoni,--a thermal spa town that dates back to Roman times--before reaching the beautiful Castiglione d'Orcia.  The monastery of Sant'Antimo is your next stop—with luck, you will hear the monks chanting.  Montalcino is your destination where wine shopping for the famous local Brunello is a must.

Day 4: Montalcino to Siena - 60 km (37.5 miles)
Your detailed directions will take you through typical postcard Tuscan scenery, Italy’s most photographed region—for good reason.  Following a picturesque crest road, you’ll ride by the Monte Oliveto Maggiore monastery—which also makes a nice lunch spot before cycling on to Siena, your final destination.  Make the best of your afternoon and explore its countless treasures such as its unfinished Duomo and its famous Piazza del Campo where twice a year the disputed “Palio” horse race is held opposing the 17 “contrade” of this fascinating city. 

Day 5: Siena to Castellina-in-Chianti – 45 km (or 28 miles)
Another day of hill climbing with many recovery sites on your way including medieval Castelnuovo Berardenga, the gateway town to the Chianti wine-producing region.  A bit further is the impressive fortress of Castello di Brolio where a wine-tasting can be done.  Your destination is Castellina in Chianti.

Day 6: Castellina to San Gimignano - 60 km (37.5 miles)
On your way, you’ll ride through the walled town of Monteriggioni that offers views in the distance of San Gimignano—your final destination—and its distinctive skyline of stone towers.   San Gimignano is exceptional (it is a UNESCO World Heritage site) and we cannot recommend enough an early arrival to discover this fascinating place.  This lively city houses a number of exceptional restaurants set in historic buildings that will contribute to making your gastronomic experience a memorable one. 

Day 7: Departure
After breakfast, depart San Gimignano a the time of your choice.  Note that you may also opt to ride a short route that will take you to Certaldo (worth a visit) where you’ll hop on a train to Florence (a 50 minutes’ ride).  Alternatively, we can arrange a car transfer from San Gimignano to Florence.

Pricing: This package has been priced at 1,310 euros per person in double occupancy. Single supplement is 350 euros.

This price includes:

• 6 night-accommodations in 3- and 4-star properties
• Daily breakfast
• Meeting with our local representative on Day 1
• Marked maps and/or cue sheets
• Luggage transfers
• Assistance if necessary
• All tax and service charges

This price does not include:

• Dinners and Lunches
• Drinks
• Travel insurance
• Bicycle rentals. Hybrid bikes are available at the price of 95 euros per bike. Racing bikes at the price of 135 euros per bike.