Cycling Tuscany Hills

Day 1 – Welcome to Tuscany! – Poggibonsi

You will arrive on your own in Poggibonsi. You will be met by our representative who will drive you to your villa in Staggia near Castellina in Chianti.

Day 2 – Colle Vald’Elsa to San Gimignano (21 miles/35 km)

Departing from Villa Lecchi, first you will encounter the fortified town of Monteriggioni with its distinctive round shape dominating the surrounding plain. On to Colle Val d’ Elsa and its glass blowing artisans, some of which you can visit. Today’s route will also take us to San Gimignano with its beautiful towers. You will want to spend some time here to explore the city and perhaps some of the village shops before starting back to Villa Lecchi.

Day 3 – Castellina in Chianti to Siena (31 miles/52 km)

Enjoy beautiful biking through winding Chianti roads among luscious landscapes with vineyards and superb wineries. Our day will end in Siena where you may enjoy a gelato (ice cream) at one of the most famous squares in Italy, the Piazza del Campo. Overnight in Siena.

Day 4 – Siena to Buonconvento (19 miles/32 km)

As you bike today you will notice lush vineyards give way to the linear cypress-crested hills of the “Crete.” Murlo is a charming little village on your way to the farm where you will spend the night. In summer months you may enjoy a refreshing dip in the swimming pool. There are also relaxing massages and a sauna available for your enjoyment.

Day 5 – Buonconvento to Montalcino (27 miles/46 km)

We start towards Buonconvento, then head for the Monte Oliveto Monastery, an imposing brick building that overlooks a rugged landscape of dry ravines. A soft downhill will take you to the start of a fairly long uphill to reach Montalcino. You will spend the night in a nice hotel in Montalcino, the home land of Brunello wines.

Day 6 – Sant’Antimo abbey loop ride (20 miles/34 km)

Enjoy this fortified town from which you will enjoy stunning views from all directions. The descending trail road will lead you to the beautiful and peaceful church of Sant’Antimo Abbey where you may be able to listen to Gregorian chants. A lovely end to a peaceful day.

Day 7 – Montalcino to Pienza and Montepulciano (27 miles/45 km)

A very full day beginning with Bagno Vignoni and its thermal pool in the center of town. On to Pienza, the renaissance jewel redesigned by the pope Pio the II to become a “liveable” town. It is also an agricultural center well known for pecorino cheese and truffle production. A dirt road will take you to Montichiello, a nice little village immersed in the “Crete.” Here you can stop for a nice lunch or a cappuccino before continuing to Montepulciano known for its “Nobile” wine.

Day 8 – Departure Day

End of our services after breakfast. Ciao!

Actual tour itinerary may vary slightly due to unforeseen circumstances.

Siciclando carefully chooses every aspect of a tour, including the accommodations.

Our choices are based on comfort and quality. We often choose hotels that are family-owned and operated because they provide a richer experience and because it is important to us to support the efforts of these individuals. We have developed relationships with many wonderful hotel operators. Here is a sample of the hotels on this tour.

• Siena
• Buonconvento
• Montepulciano

Tour accommodations will be based on availability and the time of year. Once you have made your final payment for the tour, we will send you a confirmation letter that includes daily accommodations and contact information.

Level of difficulty: Moderate

There is no easy way to tour Tuscany. It is a hilly country so with all the ups and downs, the altitude gap at the end of the day is never small. However we tried hard to keep it as smoth as possibile. The toughest day is the third, from Siena to Buonconvento and the longest is the fifth if you have road bikes and have to stay on asphalt roads.

Travel Notes

The reference airports for the tour are Perugia, Pisa, or Rome.

You can also find information about travel by train.

Books

• Under the Tuscan Sun by Frances Mayers

Movies

• Il Paziente inglese
• Ballo da sola

Group tour price

• 4-5 people € 1590 per person
• 6-7 people € 1455 per person
• 8+ people € 1280 per person

Pricing philosophy

Additional options

• Private room – € 260
• Hybrid Bike rental – € 100 (€ 18 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Road Bike rental – € 175 (€ 27 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Cooking class – € 80 per person
• GPS – € 35 Garmin E-Trex Venture HC

Included

• One English-speaking trip leader
• Seven nights in three-star hotels, all rooms with en suite bathroom
• Seven breakfasts and three dinners
• Baggage transportation between hotels
• Detailed route information and maps
• Van support

Not included

• Admission to museums and archaeological sites
• Tickets for trains or any public transportation
• Wine or beverages
• Airfare
• Transfers to the starting point or from the finishing point unless specified; we can assist you in planning and arranging for any necessary shuttles
• Transport of bike case (for guests who bring their own bike)
• Personal expenses (laundry, personal supplies, phone calls, etc.)
• Gratuity

Self-guided option

This tour is also available as a self-guided option at a cost of € 1.130 per person. This option includes:

• Seven nights in three-star hotels, all rooms with en suite bathroom
• Seven breakfasts and two dinners
• Welcome meeting (tour explanation)
• Baggage transportation from between hotels
• Detailed route information and maps
• Telephone assistance

Tour code

TU