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Terra di Siena Hike Dream - Walking - Overview

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Tour Snapshot
Duration: 8 Days / 7 Nights
Optimal Season: March-November
Area: Central Tuscany
Begin In: Montepulciano
End In: Siena
Tour Type: Walking
Avg. Daily Distance: 8 miles
Terrain: Rolling to Hilly
Roads: 65% gravel, 30% dirt/path, 5% street
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This self-guided walking tour takes you through the area south of Siena, through the Tuscan landscapes about which you have always dreamed. You will walk in the rolling hills rendered so memorably in books, films and paintings: from the world famous vineyards of Montepulciano and Montalcino, the home of the Nobile and Brunello wines, to walled medieval and Renaissance boroughs. One mid-trip transfer moves you through a lengthier section of road, allowing you to enjoy your trip to the fullest. Each day, you will visit superb churches and abbeys, stay in comfortable accommodations, and eat in quintessentially Tuscan restaurants and inns. Bellisima!


Moderate - Most days consist of rolling ups and downs with few steep climbs.


Maps, route directions, and Portable Media Player are included in the tour cost. You should provide your own daypack and, optionally, trekking poles.


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.

On this tour, we use one two-star hotel in a small village famous for its nearby monastery where no other lodging options exist. On another night, we stay one night in a four-star accommodation. The upgrade price below includes an additional five 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 in-tour transfers to Siena on Day Seven. 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:$420

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