CONNECTIONS, Connections, Connections.

It really is all about connections, but it’s also about connection itself!

For two decades we’ve been traveling the Italian countryside to meet friendly, welcoming Italians who are eager to create and host insider experiences and activities for our guests. As a result, each of our carefully crafted tours allows our guests to experience an in-depth, insider’s view of Italian traditions, culture and regional specialties.

From delightful Doriana (Umbrian truffle expert) to vivacious Cesare (hand-hammered coppersmith) to charismatic Lamberto (Renaissance paper artisan), each of our Italian “connections” is also a dear friend who treats our guests like family. Want to learn how to make real Italian pasta? Antonetta is ready to show you her best-kept secrets. Ready to learn about Italian herbs? Irma is our go-to herbal expert. How about fresh-pressed olive oil? Loredana can tell you all about it – plus offer some of his best for sampling. This is cultural immersion at its best!

Because we’ve formed these incredible relationships with our vendors, it makes it that much easier for us to help you foster genuine connection with the people and landscapes of this incredible country, as well as new connections with family and friends!

But don’t take our word for it… see what some of our over-the-moon guests have had to say »






  • Our signature style of touring is off the beaten path, classic and quintessentially Italian. We honor tradition and embrace local culture…while enjoying a bit of nostalgia.
  • We love our guests! And being our guest is just the beginning. Once you travel with us, you become part of our Strada Toscana family – an exclusive club, so to speak, of discerning travelers who enjoy exploration and discovery, along with gourmet meals and good company.
  • Our reputation as an exemplary, 5-star rated tour operator has been built almost entirely by word of mouth. More than 90% of our guests are repeat guests or referrals from previous guests.
  • A friendly evening aperitivo hour has become a hallmark of our tours, where you share, laugh and reflect on the day’s events with fellow, like-minded travelers
  • Our stellar team includes guides, hosts and drivers is based in Tuscany – and most are from families that date back centuries. They know the places, the people and the tucked-away gems like the back of their hand.
  • We choose extraordinary, boutique accommodations that beautifully reflect the character of the region, while offering outstanding services, amenities and unexpected extras.
  • No buses. Ever. Our excellent team of drivers use 8-seater, Mercedes Benz vans that allow us to access tucked away avenues and traffic-restricted historic centers.
  • Tucked away sites and cultural experiences NOT listed in guidebooks are included in each and every one of our tours.
  • We only provide tours in Italy – not multiple destinations.
  • Our maximum group size is 14 – ideal for both intimacy and independence.
  • We have your back. Each of our tours includes a primary host, a hospitality host, experienced guides, local experts and professional, friendly drivers who treat you like family.
  • Designed to both educate and inspire, our itineraries are also fun beyond your imagination!
  • Our relationships with local Italian experts, artisans and guides, who you meet throughout your journey with us, is unsurpassed. They’re not just connections, they are our dear friends, and are sure to become yours as well.
  • We advocate for the preservation of centuries-old Italian artistic traditions from fine leather goods to hand-hammered copper to Renaissance maiolica ceramics, and include visits with local artisans on each of our tours.
  • Strada Toscana – a DBA of Off the Beaten Strada LLC – is a fully insured and bonded travel company registered with the State of Florida as a Seller of Travel. Registration No. ST37452