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A tour of magical Tuscany is on every visitor to Italy’s wish list. Its breathtaking landscapes of hills, vineyards and olive orchards, lovely renaissance hilltop towns, simple yet delicious cuisine and world renowned wines offer something for everyone to enjoy. There is no better way to escape the pace of modern life and immerse yourself in authentic Italy than a walking tour through southern Tuscany.


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Join Vernon and Kathy of Italiaoutdoors Food and Wine on our walking adventure through the picturesque hilltop towns of southern Tuscany. We begin in Montepulciano, with a short walk to see the town before returning to our secluded Relais nestled in vineyards where our congenial hosts lead us in a welcome cooking class. The next day we hike along dirt roads to Pienza, a UNESCO World Heritage site, known for pecorino cheese and truffles. From the thermal springs of Bagno Vignoni, to the isolated Abbey at St Antimo, a wine tasting and tour of the renowned Brunello di Montalcino, and strolling through the medieval alleyways of charming, off-the-beaten path towns like Buonconvento and San Quirico d’Orcia, the week will continue to unfold with new sights, tastes and experiences around every bend in the road.


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Hike the Wine Roads and Hilltop Towns of Tuscany
May 21 - 28, 2017
8 days/7 nights, Tour Cost: $4395 USD ppdo

Includes: 7 nights accommodations in 3 star or better hotels, all ground transportation, 6 full days of guided walks, guide services, all breakfasts, 4 dinners with wine, including one hands on cooking class, daily wine tastings.

We're welcoming single travelers on our tours with one of the lowest single supplements in the industry - only $300!


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Limited to 8 participants, for a highly personalized experience and the best access to small local producers.

Have a small group of 4 or more? This trip can be run as a private trip for your group, for the same price. We can customize the walks for the skill and fitness level of your group, from expert hikers to casual walkers.

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pienza-walking-tour-tuscanyHighlights of our Tuscany walking tour:

  • Guided walks through the scenic countryside of Tuscany, surrounded by vineyards, olive orchards, oak woods, cypress trees and pretty villages
  • Visiting a family estate for a private tour and wine tasting
  • Enjoying a glass of Chianti with the locals at a piazza cafe
  • Daily wine tastings as we immerse ourselves in the history and flavors of the Tuscan wine scene
  • The fascinating history and architecture of Tuscany’s hilltop towns, from well-known destinations like Siena to lovely, still-undiscovered San Quirico d’Orcia.
  • Dining on our favorite Tuscan dishes: bistecca alla fiorentina with steaks from the local Chianina cattle, homemade pici pasta, many flavors of Pecorino cheeses, and the local salumi, spiced with fennel.

Our tour includes:

  • Limited to 8 participants maximum
  • pici-tuscany-walking-tour-italy7 nights accommodations at 3+ star hotels
  • All ground transfers
  • Daily guided walks
  • All breakfasts, snacks on the road as we walk, 4 dinners; the dinners include local wines
  • Wine tastings
  • Hands on cooking class
  • All tips, gratuities, and local taxes
  • Any entry fees to museums, villas, other venues we may visit
  • Services of Kathy and Vernon throughout the trip

To receive a detailed itinerary, ask any question, or to sign up, This email address is being protected from spambots. You need JavaScript enabled to view it.. We personally work with each and every guest to make sure our trip is customized to your abilities and preferences. We're also happy just to chat, and hear how you would like to travel.