We get you closer to Antonietta’s tagliatelle and Giuseppe’s sheep…to hidden abbeys and private homes…to stunning panoramas and ancient sites. You see, our small group tours of Italy are really all about YOU making connections. We get you in close – like an insider – so you can truly connect with Italy’s extraordinary culture and delightful people. Because that’s what makes your travel experience richer, more intimate and truly unforgettable. Up-close connections. That’s what we do. 

HOW We Do What We Do

Being herded like a sheep is great for…well…sheep. We create and host small-group tours (14 is our maximum number, by the way) that are different from other tours because we recognize that you’re not a sheep. 😉 You take part in delightful group experiences – like gorgeous walks, special meals or hands-on cooking lessons –  and then you have loads of personal options – like free time for shopping, or visiting museums or relaxing poolside with a good book.

Plus you travel in style (private drivers and Mercedes Benz vans all the way, baby), and although you might get your shoes dusty traipsing through a family-run vineyard, later you’ll savor a chef-prepared, gourmet meal as the sun sets behind the Tuscan hills. It’s this fabulous contrast – the RUSTIC AND REFINED – that resonates with your soul, and makes your vacation absolutely unforgettable.

WHY We’re Special 

We look at things differently. More closely, you could say. For us and our guests, it’s not enough to simply go to beautiful places (which is super easy to do in Italy). 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.

That’s why, for two decades, we’ve been exploring the Italian countryside, meeting friendly, welcoming Italians 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.) Sure we have a network of local connections and lots of experience in creating and hosting tours, but our speciality is helping you notice the beauty of Italy in all its forms. That’s why we’re special.

HOW It Works

It’s as easy as pie (or, as they say in Italy, smooth as olive oil). Once you’ve signed up for one of our tours, you’re instantly a part of the Strada Toscana family (and there’ll probably be some hugs somewhere down the line – so be prepared).

We send you a trip confirmation with a full itinerary that includes everything from packing tips to a walker’s supply list to trip extension suggestions. Our trip departures are guaranteed, so you can go ahead and make your flight arrangements too. Plus we’re always around should you have questions about virtually anything. Except which color outfit to pack. We won’t touch that one. 😉

WHAT To Do Next

Peruse our 5 STAR RATED ⭐⭐⭐⭐⭐ escorted walking tours and see which one beckons to you. Click to see dates, prices, photos, details and daily options (the hallmark of our tours) – plus fast, secure, & easy online booking. Soon you’ll be drizzling that crusty Tuscan bread with newly pressed 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

At Strada Toscana we create and host incredible walking tours of Italy. But while we walk for pleasure, children throughout the world are struggling to walk, 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.



  • 25% – 50% LOWER PRICES. We encourage you to look around for yourself. Our trip prices are 25%-50% less than other companies’ comparable vacations with comparable lodging, meals and transportation. And included experiences? Well those aren’t comparable, because ours are off the charts (said with humility and honestly).
  • WALKING. We walk with Italy in our soul as we gaze at awe-inspiring landscapes, immerse ourselves in local culture and indulge 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.
  • FIRST-TIMERS OR SEASONED TRAVELERS. Our itineraries are great for first-time visitors or seasoned travelers as well as single travelers or groups of friends or family.
  • 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 has been built almost entirely by word of mouth. More than 90% of our guests are repeat guests or referrals from previous guests.
  • 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.
  • 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.
  • 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