BUONGIORNO & Welcome to Strada Toscana! 

If you love experiences that make your heart sing, you’re definitely in the right place, because we help people like you experience Italy in unique and intimate ways.

What is Strada Toscana, anyway?

So glad you asked! We’re a boutique company that creates intimate events, weddings, retreats and family trips at a private villa in Tuscany.

Can you tell me more?

Of course!

Rent a private villa and you’ll get a villa. Go with a tour company and you’ll get a tour. Book a wedding venue and you’ll get a venue. You get what you get.

Strada Toscana is highly unique because we effortlessly customize a package of all of these things – or some of these things – just for you.

Can you give me an example?

Sure! How about two?

Let’s say you’re planning a special trip and you’d like to stay at a villa in Italy. Sweet. You find a lovely place and you’re ready to book. But what about excursions once you get there? What about experiences, like cooking lessons or wine tastings? What about meals? Who’s going to organize all this stuff?

Or maybe you’re hosting a special event, like a wedding. You find what seems to be the ideal venue, but then they inform you that they can’t help with transportation or with excursions for guests or with any of the planning. Where do you go for help?

That’s where we come in.

We create and customize trips or specials events that are based at a 17th century Italian villa. The villa is reserved exclusively for your group, and we customize your stay with any number of private excursions or insider experiences. Because our team is based in both the U.S.A. and Italy, we’re able to seamlessly gather your requests, then make it all come together.

How did you get so good at this?

Ah shucks, are we blushing?

Well, we started out as a boutique tour company that offered small group tours of Italy. We’ve traveled from Venice to Cinque Terre to the Amalfi Coast with our happy guests, helping them get to know Italy as insiders. We toured – and refined our approach touring – for more than 10 years, and then something extraordinary happened.

We got the opportunity to have exclusive use of a historic, family-owned villa located along the eastern border of Tuscany. It was love at first sight, and the rest (as they say), is history. 

Do you offer tours of Italy?

Yes, we offer a select number of tours each year. You can check them out here.

You seem different…

That’s because we are. I guess you could say that we look at things differently. More closely.

We make a point of noticing the beauty in ordinary things – the things the really reflect Italian culture at its core; like espresso in a tiny porcelain cup or a basket of freshly-picked tomatoes or Antonietta’s hands as she kneads the pasta. That’s where la bellezza of Italy lies – in the simplest of things.

Over the years we’ve explored the Italian countryside, meeting friendly locals who are eager to create and host insider experiences and activities for our guests – and to reveal the extraordinary beauty of Italy. (Some of these people have even become a part of our Strada Toscana team.)

This network of local connections is our heartbeat. ❤️

WHAT To Do Next

  • Peruse our 5 STAR RATED ⭐⭐⭐⭐⭐  tours and retreats see which one beckons to you.
  • Or contact us to book your wedding or special event. 

Soon you’ll be drizzling crusty bread with new olive oil…and sprinkling on the sea salt.


“You went out of your way to show us more than Italy’s culture, history, and beauty. You showed us Italy’s soul, as reflected in its dedicated people doing what they love, and often following in their families’ footsteps as fine artisans – handcrafting wine, cheese, olive oil, and metal work. The Italians you introduced us to love life, and love their life’s work, as you do. Their passion, and yours, touched us like no other tour, and we’ve had many. Thank you for your warm and heartfelt hosting, which has redefined vacations for us. As you know, our family is already planning another tour of Italy with you, because we won’t go with anyone but you.” —Sincerely, Beverly and Pete Bono

MEET STRADA TOSCANA’S Team Straordinario!

Our team of dedicated Italians (never foreign guides or hosts) from expert travel coordinators and delightful local guides to welcoming trip hosts and extraordinary drivers is ready to make your experience in Italy over-the-top amazing. After all, they know the land, the people, the places, the sites, the towns, the foods, the wines (and so much more) like the back of their hand. They also support our company’s vision to act as a bridge between our guests and the Italian culture, while fostering a mutual sense of appreciation and respect. These things not only make for a memorable vacation, but more importantly they create genuine human-to-human connections that touch hearts – and influence lives – in immeasurable, positive ways. Now, that’s something to get excited about!

WALKING To Make a Difference

While we explore Italy, children throughout the world are struggling to even walk to school, because their shoes don’t fit – or they have no shoes at all. That’s why we’re thrilled to partner with the Shoe That Grows, a stellar organization that makes and distributes shoes for children who desperately need them. So when you travel with us at Strada Toscana, we donate a pair of shoes to a child. You walk with us, a child walks in shoes. It’s that simple. Step by step, together we can make a difference.


Strada Toscana is a proud member of the Adventure Travel Trade Association, working to preserve local cultures and encourage sustainable travel practices. From encouraging the use of reusable water bottles to supporting local economies to teaching guests about preserving historic sites, we’re committed to improving tourism with thoughtful travel practices.



  • SOUL STRUCK. We explore with Italy with our soul as we gaze at awe-inspiring landscapes, immerse ourselves in local culture and indulge in incomparable food & wine. We traipse through vineyards and along cobblestone streets by day, indulge in gourmet meals and outstanding wines by night, then retire to luxurious, boutique accommodations to rest and relax for the next day’s adventures.
  • BETTER THAN ON YOUR OWN. Many of our guests are used to traveling on their own so we’re honored that they choose to travel with us, and then return to travel with us again and again. The reason? They tell us it’s because we have connections that they could NEVER find on their own, we travel the way they would on their own – with gusto, enthusiasm and spontaneity – and that they LOVE us taking care of all the planning and logistics. Every last detail.
  • OPTIONS. We recognize that each of our guests is fabulously unique, so our itineraries include flexibility and plenty of options for those who prefer fewer steps or more steps. Plus we love a healthy dose spontaneity.
  • WE LIVE HERE. Our team of guests, experts and trip leaders are not only Italy specialists, they also live here – some coming from families that date back centuries. This means you can expect delightful, spontaneous experiences with locals throughout your tour.
  • RESPECT. Our steadfast commitment to treat each tour – and each tour guest – with the utmost respect and attention is unrivaled.
  • AUTHENTIC EXPERIENCES. We know that each of our guests is fabulously unique, we include delightful variety of authentic experiences, hands-on activities, spectacular walks and irresistible options.
  • A SENSE OF WONDER. Strada Toscana was founded on a mission to bring a sense of wonder back to travel, by acting as a bridge between our guests and the Italian culture, and by fostering a mutual sense of appreciation and respect. We believe these elements not only make vacations memorable, but create positive human to human connections that touch hearts and change lives. In fact, we know it first hand!
  • 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 and event facilitator has been built almost entirely by word of mouth. More than 90% of our guests are repeat guests or referrals from previous guests.
  • 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