Things to do in Tuscany

Imagine yourself in Tuscany.  Seated on your terrace, you sip espresso and gaze over Montalcino’s vineyard-draped valleys. Nearby, you spot a stone farmhouse — crowned in terracotta tiles. As the sun rises over this heavenly scene, the town’s piazza gets painted in gold light. “This,” you think to yourself, “is the Italy I’ve dreamed of.”

Let us help you to unlock the Tuscany that few tourists experience. You’ll savor the undiscovered Tuscany, immersing yourself in hilltop towns and unspoiled scenery. Whether you’re enjoying a behind-the-scenes wine tasting near Siena or making pasta in Florence with an Italian chef, Tuscany tempts all kinds of travelers. So, what are the best things to do when you travel to Tuscany, Italy?

Brimming with medieval villages and castle-crowned hills, Tuscany is a must-see both for first-time visitors and well-heeled Italy explorers. In the region’s untouched hamlets, time seems to stand still. In Pienza, you’ll eye neighbors sharing a caffe (coffee) on cobblestone streets. And in the Renaissance gem of Lucca, you’ll see locals strolling atop the city’s centuries-old walls. 

There’s much more to Tuscany than the Leaning Tower of Pisa. When you travel to Italy, this is how to experience the crowd-free Tuscany:

Tasting Tuscany 

Cucina povera – rich dishes born from humble ingredients – typify Tuscan food.  Cooks in Tuscany don’t rely on fancy techniques or elaborate plating.  All they need is quality ingredients that sing with natural simplicity. Olive oil. Fresh pasta. Wild game. Garden vegetables. Hungry travelers are in heaven in Tuscany – relishing the region’s simple-yet-savory table.  

But, how can a food-loving traveler taste the real Tuscany? Below is a sampling of what you might enjoy when traveling with us:

After breakfast in your historic town, a private driver will bring you to our Tuscan chef’s farm in the hills of Chianti. First, you’ll pick ingredients from his garden. Next, you’ll prepare together an old-fashioned Tuscan feast — honoring seasonal flavors and Slow Food techniques. Lunch is served outside, overlooking Castellina in Chianti’s lush vineyards and silvery olive trees. Along the way, our chef will regale you with stories from his childhood – growing up in the hills between Siena and San Gimignano.

Looking to avoid the crowds? Head instead to the charming Val d’Orcia – a cypress-lined valley in Southern Tuscany.  Here, you might sip red wines at a family-run winery – tasting vintages that age for 3 years in oak barrels.  For a food-filled excursion, you can enjoy a homemade lunch at a local, family-owned pecorino cheese farm – savoring a meal al fresco, gazing out over the roll hills of Tuscany. 

When you travel with us, you won't end up in tourist trap restaurants with mediocre food. We show you the real Italian food you crave.

Brunello, super tuscans, and more...

Tuscany’s mineral-rich soil is ideal for the growing of grapes.  The region’s rolling hills house countless wine-producing vigneti (vineyards) and tenute (estates) – including Sangiovese (red), Vernaccia (white), and vin santo (dessert).

Near the picturesque towns of Montepulciano you’ll  find some of Tuscany’s finest (and most scenic) wineries. Led by our local guide, you will first stroll Montalcino’s medieval streets — visiting the city’s 13th-century castle. After Montalcino, you will head to the countryside to enjoy a private tasting of Brunello wine in the cellars of the vineyard — paired with a traditional Tuscan banquet.  

A bit closer to the Renaissance jewel of Florence are the world-famed Chianti hills.  Chianti is a region of Tuscany just outside of Siena – renowned for its fruity Sangiovese blends and rolling hills.  Medieval towns here include Radda, Greve in Chianti, and Gaiole.  In each, you can wander meandering stone streets and drink in sweeping views of the surrounding wine country. 

Your driver in Tuscany might whisk you away to some of Chianti’s most treasured vineyards – unlocking private cellars not open to the tourist crowds. Your charming Tuscan driver is also a trained sommelier. Notably, she’ll introduce you to the people – the Tuscan locals – who continue to nurture Tuscany’s centuries-old wine-making traditions. 

If you’re a wine-sipping traveler, you can even stay overnight in a winery estate—like Castello Banfi.  You’ll slumber inside medieval towers. You’ll traipse grape-lined hilltops. And, you’ll sip prized vintages in the company of the people who call this place home. Overnighting at a winery estate is the perfect romantic escape, whether you’re celebrating a big anniversary or journeying through Tuscany on your honeymoon.

Tuscany is rightly synonymous with hilltop towns. Tourist-free hamlets abound here beyond popular stops, like Siena or San Gimignano. Since the middle ages, Tuscans have built their cities and towns on top of the region’s bountiful hills — giving the locals unobstructed views of the valleys and vineyards below. Towns – like Volterra, Pitigliano, Barga and Pienza – all boast winding stone streets, historic palaces, and sweeping vistas.

Many also feature their original defensive walls and tall stone towers. A perfect way to explore these town is with an expert Tuscan guide. After discovering Tuscany’s tourist-free backstreets, you’ll dine in the trattoria locals love – enjoying the scent of fresh-from-the-oven focaccia salads and extra virgin olive oil. Check out 4 Tuscan hilltop towns you need to explore.