Fall in love with Tuscany ... off the beaten path

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​​​​VINTAGE Toscana Small Group, Gourmet, Walking Tour - 6 Days/5 Nights
For Active Travelers with a Spirit of Adventure ...
Unpack just once! No hotel hopping!

Designed for seasoned travelers, first-time visitors, friends, couples, and solo travelers who want more than an ordinary sightseeing tour, our Best Tuscany Small Group, Gourmet Walking Tour features the region's rich heritage through its delectable culinary traditions, precious artisans, hidden hamlets, ancient civilizations, medieval marvels, exceptional wines and so much more. The ultimate in small-group walking tours of Tuscany, our Tuscany Tour includes options each day for both walkers and non-walkers.

  • WHEN: 6 Days/5 Nights - See Dates
  • WHO: Seasoned travelers, first-time visitors, couples, friends, relatives and solo travelers are all welcome on this tour (No single supplement fee!)
  • WHERE: Based at luxury, boutique hotel, Villa Poggiano, near the Renaissance hill town of Montepulciano in Tuscany's quintissential wine country, you'll be visiting postcard-perfect villages in and around the impossibly beautiful Val d'Orcia and Monte Cetona. 
  • WHY: The Best Tuscany Small Group Gourmet Walking Tour allows you to experience this famous region's culture, traditions and people as an insider (not as a tourist!), to learn more about the area's incredible history, artisans, artists, foods and wines, and to form lasting friendships with like-minded fellow travelers and welcoming Italians.

Tuscany as an Insider
We live in Italy, along with our Off the Beaten Strada team, and we KNOW Tuscany. For more than 15 years we've been traveling and exploring the Tuscan countryside, meeting friendly, welcoming Italians who are eager to create and host insider visits, experiences and activities for our guests. As a result, each carefully crafted small-group tour of Tuscany allows you to experience an in-depth, insider's view of the region's irresistible traditions, culture and regional specialties.



Benvenuto in Italia! Upon arrival at Florence Peretola Airport, sit back and relax as you are transported via our private Mercedes Benz van service to the Tuscan countryside and historic Villa Poggiano - your elegant accommodations near Montepulciano. After check-in you'll have an opportunity to relax and settle in before enjoying a friendly trip orientation and garden tour with the villa's owner, Stefania. Afterwards you'll have time to explore on your own before getting together for an aperitivo hour followed by a delicious welcome dinner prepared by an award-winning Tuscan chef.
Dinner included

Note to History Buffs:

  • Built in the 18th century as a summer house, Villa Poggiano belonged to the noble Gagnoni family of Siena. The villa passed to a German military officer at the beginning of the 20th century, who was forced out by locals during World War II. The villa then passed from owner to owner, and when the Savini Family purchased the house in 2000 it was nearly abandoned and in total decline. After years of extensive restoration - a labor of love - the grand villa was opened as a classy, boutique hotel.


Early morning village walk Monticchiello (optional), private visit with hand-hammered copper artisan, private Vino Nobile tasting and lunch in our friends' 15th century cantina, Montepulciano historic center, optional walk to San Biagio or time on your own in historic center, vineyard photo op, bruschetta-making lesson, gourmet dinner at Condè Nast Traveller recommended, La Grotta
Breakfast, lunch and dinner included

  • MORNING: After breakfast, those who wish may opt for an early morning walk in the charming Tuscan village of Monticchiello. Then it’s on to regal Montepulciano with its Renaissance palaces and spectacular views. We begin in the historic center of town with a fun, private visit with Cesare, a delightful copper artisan, whose hand-hammered cookware is nothing short of stunning. Then we're off to our friends' 15th century cantina for a private wine tasting that includes world renowned Vino Nobile di Montepulciano and Vino Nobile Reserva - among Tuscany's finest DOCG wines.
  • LUNCH: A light lunch will be served during our private wine tasting in our friends' 15th century cantina (save room for gelato later!)  
  • AFTERNOON: Enjoy time on your own for shopping (we'll point out our favorite artisan shops), wandering or grabbing a gelato.Those who wish, may opt for a guided walk from Piazza Grande to the Renaissance cathedral, Tempio di San Biagio, while non-walkers may enjoy shopping or museum visits on their own.
  • LATE AFTERNOON: Photo op in a picturesque Vine Nobile di Montepulciano vineyard.
  • EVENING: Aperitivo hour, followed by a delectable dinner at our friends' Montepulciano restaurant, La Grotta - praised by Condè Nast Traveller and Michelin Guide.

Note to Wine Enthusiasts: 

  • The wine produced in Montepulciano, Vino Nobile di Montepulciano, was dubbed “the noble wine” during the Renaissance and is one of just 74 DOCG designated wines in Italy. There are approximately 2,000 grape varieties in Italy, so the production of a top-level DOCG wine means tight rules and regulations to ensure the quality and authenticity of the wine.


DAY 3: SARTEANO, SAN CASCIANO DEI BAGNI ...Click to View the Complete Itinerary






Behind the Scenes
Without our dear friends, partners and collaborators throughout Tuscany, our tours there would be ... well ... just like any other. What makes our Tuscany itineraries truly special are the Italians artisans, history buffs, winery owners, pasta makers, herbalists, nature lovers, art experts, culinary enthusiasts and so many others, who welcome our guests like family and generously share their culture, traditions and best-kept secrets. Their vast, first-hand knowledge of Tuscany has helped us create the BEST, culturally rich, small-group Tuscany tour!