Best Small Group, Gourmet, Walking Tours

VINTAGE Toscana Small Group, Gourmet Walking Tour

For Active Travelers with a Spirit of Adventure


  • Unpack just once! 5 nights stay at boutique, luxury hotel Villa Poggiano, recommended by Michelin Guide and Karen Brown, and member of the Italian Luxury Guide. Owner-operated by our friend, Stefania, Villa Poggiano is nestled in spectacular wine country near the Renaissance hill town of Montepulciano. Along with luxury linens, upscale amenities and gourmet, chef-catered meals, you'll enjoy roomy sleeping rooms (painted by Italian artisans), all with elegant, ensuite marble bathrooms.

  • Private Mercedes Benz van service to/from Florence Peretola Airport upon arrival and departure, and to/from all towns and sites included in the itinerary. Our carefully selected drivers - from the Montepulciano area - are professional, friendly and are an integral part of our tours.

  • All buffet-style breakfasts with a multitude of delicious choices, including eggs, yogurt, cold cuts, cheeses, fruits, pastries, breads, and cereals - plus teas, juices and made-to-order Italian coffee. Gluten-free or dairy-free items are always available upon request.

  • Three delicious lunches featuring regional specialties and accompanied by DOC regional wines

  • All delectable dinners, featuring regional specialties and accompanied by DOC regional wines served at Condè Nast and Michelin award-winning restaurants along with villa meals prepared by one of Montepulciano's finest catering chefs 

  • Private visit with our friend, Cesare, a hand-hammered copper artisan - one of very few remaining in all of Italy. Cesare's cookware is coveted by chefs around the world, and his unique copper designs are stunning.

  • Tour and cheese tasting at our friends' organic sheep farm, using traditional, natural cheese-making methods that result in extraordinary fresh, semi-aged and aged pecorino

  • Light lunch and VIP tour at awarding-winning Ciacci Piccolomini d'Aragona Winey with its unique design and outstanding DOC brunello wines


  • Chef-led "pici" pasta-making lesson at Villa Poggiano

  • Photo opt in Val d'Ocia - one of the most photographed areas in Tuscany, with its winding, cypress-lined roads, rolling wheat fields and characteristic Tuscan farmhouses 

  • Tour of 14th century Castello di Sarteano

  • Tour of "hidden" Etruscan Necropolis

  • Private tour of Villa La Foce gardens with its spectacular views of the Val d'Orcia

  • Daily, guided countryside and village walks, including the Val d'Orcia village to village walk, Monticchiello ring walk and Pienza passeggiata walk -along with daily options for non-walkers. Note that walks are easy to moderate. 

  • Visits and tours with top-notch English-speaking Italian guides, all from the area in which we travel

  • Organic, artisan toiletry products - all made in Tuscany

  • Entrance fees to all sites included in trip itinerary

  • Evening aperitivo hours featuring guest favorites from wine spritzers to Prosecco to light wine pairings, along with friendly conversation an reflections on the day

  • Daily accompaniment with Pamela Haack and/or Off the Beaten Strada team hosts and guides

  • Restaurant gratuities

Not Included: Airfare, travel insurance, lunches, wine or other alcoholic drinks, inner-city bus, metro, train or boat transportation outside of those specifically listed in the trip package. Tips for service providers, including villa staff and drivers.

Ready to walk along the breath-taking Val d'Orcia, explore Etruscan tombs, and taste top-notch Tuscan wines at a family-run winery? On the Best Tuscany Gourmet Walking Tour you'll be living Italy through a rich itinerary that allows you to experience centuries-old traditions and local customs as an insider. Plus we've included private demonstrations, visits and tours with local Italians (never foreign guides) who live and work in the regions in which we travel. Be prepared to be delighted and amazed each and every day of your journey.






Copyright © 2017 Off the Beaten Strada in Italy      Contact Us