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Terra di Siena Bike Dream - Biking - Overview

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 Zephyr's Virtual Tour Guide is included in this tour. Click here to learn more.
Tour Snapshot
Duration: 7 Days / 6 Nights
Optimal Season: April-October (July and August can be hot)
Area: Central Tuscany
Begin In: Arezzo
End In: Arezzo
Tour Type: Biking
Avg. Daily Distance: Main Routes 28 miles
Long Routes 40 miles
Terrain: Rolling to Hilly
Roads: 86% asphalt
Map This Adventure


This self-guided biking tour takes you through the hilly region east of Siena (and southeast of Florence) offering classic Tuscan images at every turn: hamlets and hill towns, terracotta rooftops, swaying cypress, and golden valleys. The lovely roads that runs from Val di Chiana to the Etruscan town of Cortona and from Montepulciano towards Pienza are the main paths into the heart of central Italy. The roads we use are both paved and dirt. Climbing and descending the distinctively Tuscan hills, all your efforts will be rewarded by the perfect views that are nature's works of art. In each of the towns along this route, locals gather in the piazza every afternoon, walking in the "corso" (old town's main road), strolling with friends or looking for a good espresso. This simple way of life is Italy's best kept secret and your invitation to a fantastic self-guided vacation.


More Difficult - Because of the hills in Tuscany, this tour requires a good level of physical fitness. You can always walk your bike if necessary! Please note our biking tours do require you deal with basic bike repair issues such as changing a flat tire or replacing a derailed chain.


You have the option to bring your own bike, or to rent a high-end Cannondale and Viner aluminium 27-speed touring bicycles with drop-down or upright handlebars. Each bike includes a front or rear handlebar bag, water bottle, lock, cycle computer, repair kit (including a spare tire), and pump. You can choose to have standard pedals or (if you plan to bring your own pedals and shoes) we will remove the pedals entirely.

Maps, route directions, and Portable Media Player are included in the tour cost.


Accommodations consist of three-star hotels and B&Bs. We spend a lot of time finding hotels with local charm, friendly proprietors, and excellent locations. If you would like to upgrade, we will reserve your room in a nearby four-star establishment when possible or upgrade your room in the initial hotel when not. For some nights in small villages no upgrade option is available and the upgrade price below reflects this.

For this tour, the upgrade price below includes three nights in an upgraded hotel.


All prices below are in US dollars, per person, for a minimum group size of two. The Base Price for all adventures includes a Pre-Departure Packet, double occupancy accommodations in three-star hotels, breakfasts, welcome meeting with our in-country staff, luggage transfers, maps, route directions, emergency support phone line, and one transfer back to Arezzo on the last day. Dinners, lunches, personal expenditures, and transportation to and from the tour are not included. See our Pricing Page for full details on our Base and Supplemental prices and information on travelers going solo.

Adventure Prices
Base Price:$1,900
Hotel Upgrade:$300
Single Room Supplement:$360
Bike Rental:$150

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