100km of Chianti
a transformative trek & tasting adventure
This transformative journey through the Chianti wine region begins in Florence, the cradle of the Renaissance. Led by your private guide, Emanuele, you will depart along the historic Via Romea Sanese, tracing an ancient route through manicured vineyards, olive groves, and storied hill towns before arriving in the medieval splendor of Siena. Each day unfolds at a considered pace, balancing purposeful walking with moments of rest, tasting, and discovery.
Along the 100km route, you will retreat to four carefully selected sanctuaries of comfort and restoration, including the enchanting villages of San Donato in Poggio and Castellina in Chianti. Expect understated luxury, exceptional local wines, and an intimate connection to Tuscany’s landscape, history, and culinary traditions.
Highlights
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Spend one night in Florence before embarking on a hike through the Chianti wine region and spend one night in Siena at the end of the road.
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Travel the ancient road connecting Florence and Siena, tracing the footsteps of millennia of travelers. Each leg of the journey will be guided by our Chianti expert and environmental guide, Emanuele.
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Endulge in trailside picnics memorable evening meals with tastings in the the best eateries and wineries of the region.
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Witness mind-blowing views of The Chianti and enjoy cherishable encounters with local foragers, shopkeepers, chefs, and more.
Included
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8 unique stays in charming Tuscan Hotels and Agritourisms.
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Private ground transportation as indicated in the itinerary and daily luggage transfers between hotels, while you trek.
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All meals are included
Breakfast each morning at the hotels and agritourism
A variety of picnic style and tasting lunches will be provided on the hiking trail
Elegant dinners each evening in the region at local trattorias and restaurants
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Full time accompaniment & expertise provided by your guides, Andee & Emanuele
8 day guided hiking experience in Tuscany,
2 Winery Visits & Tastings
1 hands-on cooking class and dining experience with a local chef
Registration
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Starting at $6,850 per person
$700 Single Supplement
Groups of 6 or more travelers
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October 18-26, 2025
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Send an email to andee@travelingnative.com to inquire about availability for your private group during the following time periods:
February - June
September - November
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Personalize your journey through the Chianti with add-on excursions and tastings. Take some time away from the trail and explore the local culture: Winery Visits, Cooking Class, Cheese Tastings and more...
100 KM of Chianti
Florence, Chianti, & Siena
October - June
Join Andee and Emanuele and fellow outdoor enthusiasts in Chianti for a week of trekking and tasting along one of Italy’s most ancient roads, La Romea Sanese.
Via Romea Sanese
Starting in the Middle Ages, Via Romea Sanese was the ancient pathway that connected Florence to Siena, two medieval cities who were in perpetual conflict.
It traverses what is now the renowned Chianti Wine Region and follows along part of what is an even older path of the prehistoric Estruscan civilization.
Traveled originally by merchants, soldiers, and pilgrims who were heading south to Rome, it was an alternate route to the famous Francigena road.
Historical highlights of the trail include the home where Nicolo’ Machiavelli wrote his famous work, “The Prince” while in exile by the Medici Family, The Benedictine Abbey of San Michele Arcangelo, Badia a Passingnano, and Castellina in Chianti.
