Sidestep the crowds in Florence and Pisa and get a more authentic taste of one of Italy's most beautiful regions with this enchanting list. Find hidden piazzas perfect for an aperitivo (aperitif) and artisan workshops that have been in business for centuries—or, dip into the countryside where lyrical landscapes unfold to reveal hill towns and tucked-away farm stays. Read on for our tips on Tuscany's best immersive experiences.

Visit Artisan Workshops in Florence

Hand-marbled Florentine paper in the making

What a difference going a few streets over can make. Cool, creative, and reached by stepping across the Ponte Vecchio to the other side of the Arno River, Oltrarno is Florence's alter ego. This historic warren of narrow, café-lined lanes hides a cluster of wonderfully atmospheric artisan workshops, some of which have been doing a brisk trade since the late Middle Ages.

This chimes neatly, of course, with the Florentine obsession with la bella figura, loosely translatable as ‘cutting a fine figure.’ In other words, attention to detail and a love of beautiful things matter. Push open the humble door of an old palazzo and observe swift fingers fashioning everything from ceramics and leather to gold and glass.

Among our favorites for picking up one-of-a-kind gifts are Alessandro Dari, the atelier of a master goldsmith, whose flamboyant, richly jeweled creations are exquisitely sculpted and inspired by 400 years of family tradition, with themes ranging from Gothic and Etruscan to Renaissance alchemy. Head over to old-world bookbinder Omero Benvenuti for beautiful hand-marbled paper and books bound in natural leather using age-old techniques and tools. The walls are a patchwork collage of wooden shoe lasts at Roberto Ugolini, world famous for made-to-measure shoes, as well as musky fragrances inspired by the waxes and polishes.

Then, stop by the Moleria Locchi ‘laboratory’ to see crystal and glassware forged using traditional blowing techniques, Atelier Via Maggio for handmade table linens, Castorina for intricate wood carvings, and Madova for super-soft leather gloves in every imaginable color.

See more locally-minded ideas in Getting Off the Beaten Path in Florence.

Enjoy Food (and Wine) at the Source

Wine tasting in the vineyards of Chianti

Mangiare bene (eating well) is considered a right not a privilege in Tuscany, and experiencing its gourmet produce at the source is the direct route to the region’s incredible food culture.

You could begin your culinary tour of the region by hooking onto one a guided tour or tasting. One of the most fun is hunting for the rare and highly sought-after tartufo bianco (white truffle), which pops up underground in the misty fall woods around the town of San Miniato, midway between Pisa and Florence.

White truffles are found between September and December. These one- to two-hour walks with a trifolau (expert truffle hunter) are often followed by a truffle feast of a lunch. And if you want total indulgence, come on one of the last three weekends in November to see some serious sales going on at the truffle fair. While you’re in town, be sure to stop by Sergio Falaschi’s butcher shop-cum-restaurant for some of the best salumi (cured meats) in these parts.

If you fancy some wine and thick green extra-virgin olive oil to go with your truffles, the romantically hilly, vine-striped Chianti region between Florence and Siena beckons. Here you’ll find an abundance of wineries (producing noble reds), organic farms and mills where you can go for tours and tastings. Single-estate bottled olive oil is the most highly prized and November is the best time to visit as that’s when the olives are harvested and pressed.

Other great wine areas for slow touring include Montepulciano (producing plummy reds grown in the Abruzzo region) and Montalcino south of Siena (the heartland of full-bodied Brunello reds). See more about Italy's wine regions in this guide

Slow the Pace with "La Passeggiata"

Siena's Piazza del Campo at dusk

For a little slice of Italian life, join locals on la passeggiata, the early evening ritual of going for a leisurely stroll through the historic heart of a city or along a lungomare (seafront promenade), often dressed in their finery. No matter how busy locals get, they like to make time for this unhurried tradition once the heat of the day has subsided and the light has softened. Always lovers of la vita bella (the good life), Tuscans wholeheartedly embrace this tradition.

When the crowds have thinned out in Florence, you could begin at the mighty Duomo and devote an hour or so to crossing the historic center, heading down to the banks of the Arno River and over the Ponte Vecchio to the quaint alleyways of the Oltrarno neighborhood.

Ringed by the most impressive and intact Renaissance city walls in Italy, Lucca is perfect for la passeggiata. At sunset, walk along its shady walls for fine views across the tower-dotted center and out to the mountains beyond. Siena’s medieval lanes are made for strolling, too, leading to magnificent café-rimmed piazzas, Gothic palazzi, and hidden corners. But these are just a few examples: la passeggiata happens anywhere and everywhere here.

Spend the Night at an Agriturismo

Classic views of the Tuscan landscape are what you can expect at an agriturismo

If your imagination has been captured by the book and movie Under the Tuscan Sun, you’ll surely be keen to experience Tuscany’s rural romance. And there’s no better way to do precisely that than by booking your stay at one of the region’s many agriturismi, working farms that offer an authentic welcome, an insight into the culture and often the dreamiest views across landscapes shaped by vineyards, wooded hills and fields billowing with poppies and sunflowers in summer.

At these peaceful retreats, days unravel gently over lazy breakfasts featuring farm-fresh cheese, milk, eggs, and homemade preserves, afternoons spent walking and cycling in beautiful surrounds, and evenings where your host-chef cooks delicious multi-course dinners for you—often served alfresco.

Agriturismi vary wildly in style and facilities: some are on wine estates, some offer cookery courses, some have outdoor pools, others are perfect for families with farm animals for children to pet. You’re bound to find one to suit your needs and budget, but do your research first. Oh, and you’ll undoubtedly need to rent a car (see more here about Getting Around in Italy).

Find more unique lodging ideas in Beyond Hotels: Unique Places to Stay in Italy.

Attend a Seasonal Festival

Carnival in Viareggio

Like all high-spirited Italians, the Tuscans love nothing better than a good festa (festival) and timing your visit to catch one can enrich your travels here no end, as well as give you a deeper appreciation of the region’s history and culture.

Things kick off in February with an entire month of huge and impressive costumed parades, wild parties and fireworks at the Carnevale di Viareggio on the coast, one of Italy’s biggest carnivals. Settimana Santa (Easter week) brings a trail of religious costumed processions to villages and towns across the region, some of which are torchlit. On Easter Sunday, the must-see event is the Scoppio del Carro (Explosion of the Cart), a medieval tradition where an oxen-driven cart is led to the Duomo in Florence before erupting into colorful flames and fireworks.

Things ramp up a notch in summer with the likes of the Luminaria di San Ranieri in June, when the whole of Pisa is aglow with thousands of candles to honor the city’s patron saint, San Ranieri. Other highlights include the medieval pageants at Ferie delle Messi in the hill town of San Gimignano (June), Siena’s wild horseback races at Il Palio (July and August) and the month-long Lucca Festiva (July). And if classical music is more your thing, you won’t want to miss open-air opera at the Puccini Festival, staged in the little town of Torre del Lago, where the great composer once lived and is now buried.

For a true tailored mix of local and cultural experiences, check out our 14-day Explore Tuscany itinerary.