Hidden Tuscany’s Treasures Await
Small Group Tuscany Tours
A tapestry of rolling vineyards, medieval villages, and time-honoured traditions.
Discover the Magic of Tuscany with Untold Italy Tours
Discover the hidden Tuscany you’ve always dreamed of – slowly on a scheduled group departure or a private tour experience.
Wander through medieval hill towns, breathe in the scent of sun-warmed olive groves, and feel the rhythm of life shaped by seasons, harvests, and heartfelt hospitality. From castles and cypress-lined roads to rustic feasts and elegant Chianti wines, Tuscany is a living masterpiece that invites you to linger, taste, and truly connect.
Each season tells its own story here. In spring, when the hills turn vibrant green, fresh fava beans, delicate fried acacia flowers, and handmade pasta celebrate the region’s rebirth.
Come fall, Tuscany glows golden – truffles perfume the air, new olive oil gleams like liquid sunlight, and vineyards hum with the spirit of harvest. There’s porcini mushrooms, saffron and earthy chestnut to feast on.
Whether exploring the countryside of Southern Tuscany or savoring long lunches under the Tuscan sun, every moment offers a deeper glimpse into authentic Tuscan life and memories that will stay with you long after you’ve returned home.
How to choose your tour of tuscany
Choose from three different Tuscany itineraries – each with their own magic and centered around the seasons, the local people and their traditions:
- Tuscany in Spring: Choose this if you want to experience both the Chianti countryside and the charms of a small Tuscan city. It’s also prime cheese-making season.
- Tuscany in Fall: Choose this if you want to embrace the harvest season – olive oil, grapes, truffles and mushrooms.
- Southern Tuscany: choose this if you’re looking for a relaxed escape in the Tuscan countryside with thermal baths and Brunello wine.
Tuscany in Spring and Tuscany in Fall tours are most popular for first time visitors to Italy. Journey into the iconic Chianti hill countryside and visit medieval towns like San Gimignano. Stay in a fairytale hamlet in the countryside and have a few nights in the beautiful walled town of Lucca.
Southern Tuscany is a little slower-paced, with a day dedicated to complete rejuvenation at the thermal baths or an exhilarating e-bike ride through the countryside. Instead of the Chianti hills, stay in the deep southern Tuscan countryside and explore Siena, Montepulciano, Montalcino and Pienza.
If you are dreaming of feeling part of Tuscany, not merely observing from the sidelines and ticking off a checklist, all of these tours are for you.
Browse our upcoming trips
Upcoming Tours of Tuscany
Discover the Tuscany You’ve Always Imagined
There’s a rhythm to Tuscany – found in the rustle of olive trees, the warmth of a shared table, and the simple joy of living well. Here, traditions aren’t just remembered – they’re celebrated every day.
Classic cypress trees and vineyards
Why our guests love our tours of Tuscany
Frequently Asked Questions
To experience the Tuscany you’ve been dreaming of in real life with people who care deeply about how you feel and not just where you go.
You’ll be invited into the homes of inspirational locals like Valentina and her goats and Lorenza and her magnificent palazzo; roll pizza dough at Francesco’s home while his cousin pours you some of his homemade wine; trudge the forest floor in search of truffles with Letizia’s dogs; sip Sangiovese wine with Piero – the maker; and learn to taste olive oil like a pro.
Our tours of Tuscany are not for you if you want to see everything but you will love this experience if you want to feel part of Tuscany. They’re for people who want to be part of it. You’ll cook together, dance together, share stories and feel genuinely cared for along the way.
- Tuscany in Spring: A journey into the famous Chianti hills and elegant Lucca. The countryside bursts into bloom, the air is fresh, and every village feels alive with the new season. Enjoy learning about the native iris flowers during a special seasonal walk. Prime cheese making season!
- Tuscany in Fall: it’s all about harvest season in the Chianti hills. The region glows with golden light, cooler temperatures and is the perfect time for seasonal activities like truffle hunting and new season olive oil tasting.
- Southern Tuscany: a more ‘unexpected’ adventure in the Tuscan countryside – not in Chianti. A relaxed pace with a day dedicated to rejuvenating at the thermal spas and a half day in wonderful Siena.
Tuscany in Spring and Tuscany in Fall trips start and end in Florence.
Our Southern Tuscany trip starts and ends in Rome.
Both seasons are magic. In Spring, the countryside is full of color, blooming flowers, and the days are longer. It’s prime cheese-making season and we enjoy dishes featuring seasonal sweet peas, fava beans, asparagus and artichokes.
In the Fall, the harvest season is in full swing. There is the grape and olive harvest for making wine and olive oil, and chestnuts, porcini mushrooms, and truffles are in season. The temperatures start getting a little cooler and days get shorter and cosier.
Yes! We always include free time most days so that you can linger longer in the places you’re most interested in and relax back at our beautiful accommodation. All the activities are optional, so if you prefer to have more free time you can do this too.
Discover Tuscany
Frances Mayes’ Under the Tuscan Sun may have cemented this region’s popularity with today’s traveler but there are still many quiet, undiscovered parts of Tuscany waiting for you. If you’ve dreamt of falling back through time in Italy, make sure to seek out untold Tuscany.
Read
Tuscany Travel Guide
Our guide to bella Toscana
Read
Picturesque towns of Tuscany
Which will be your favorite?
