Tuscany—a name that conjures images of rolling vineyards, golden sunsets, and Renaissance masterpieces—is often squeezed into a day trip from Florence or Rome. But to rush through Tuscany is to miss its soul. This region deserves lingering. From hilltop towns to gourmet lunches, hands-on countryside adventures to thermal spa indulgence, Tuscany offers a timeless slice of Italy best savoured slowly. Here’s how to spend six ideal days immersing yourself in its charm—with experiences designed for couples and families alike.
Day 1: Arrival and a Taste of the Countryside
Ease into Tuscany’s rhythm by checking into a countryside villa or heritage property near Montepulciano or Chianti. One exceptional option is Castello di Velona Resort, Thermal SPA & Winery in Montalcino. This restored fortress offers sweeping views over the Val d’Orcia and its own natural thermal springs—perfect for easing into the Tuscan pace.
Spend your afternoon exploring a nearby winery. Estates such as Avignonesi and Castello di Ama offer guided vineyard walks, cellar tours, and tastings. Children are often entertained with grape juice samplings and visits to the estate’s animals or gardens.
ET Recommends: Dine al fresco under the stars with local specialities like pappa al pomodoro and handmade pici, either hosted by your villa or at the resort’s panoramic terrace restaurant.
Day 2: Siena and the Art of the Piazza
Begin your day in Siena, Tuscany’s gothic jewel. The shell-shaped Piazza del Campo buzzes with local life—ideal for children to roam safely and for couples to savour a coffee at a historic café. Climb the Torre del Mangia for panoramic views and visit the Siena Cathedral, where marble inlays and intricate mosaics captivate all ages.
Wander the medieval lanes for artisanal boutiques and gelaterias, then settle in a shaded courtyard to soak up the city’s character.
ET Recommends: Visit the Museo Civico inside the Palazzo Pubblico to admire Lorenzetti’s famous fresco cycle—one of the earliest visualisations of good governance in art.
Day 3: Val d’Orcia – A Living Postcard
The Val d’Orcia is the Tuscany of dreams—rolling golden fields, lone cypress trees, and honey-hued towns perched on hilltops. Drive through this UNESCO-protected region and stop at Pienza, renowned for its pecorino cheese and Renaissance architecture. It’s also a favourite for hands-on family cooking classes where you can learn to make gnocchi and tiramisu.
Further along, Montalcino welcomes wine lovers with Brunello tastings in centuries-old cellars. Meanwhile, the landscape invites lazy picnics, casual strolls, and postcard-perfect photo ops.
ET Recommends: Pick up fresh bread, cheese, and fruit for a spontaneous picnic between the hills of Pienza and San Quirico d’Orcia—simple, scenic, and soul-filling.
Day 4: A Day at Fattoria di Tegoni – Farm Life, the Tuscan Way
Today, swap sightseeing for something truly immersive at Fattoria di Tegoni, a family-owned ranch and working farm. Located near Monticchiello, it offers a full-day rural Tuscan experience ideal for both families and couples. Begin with an introductory horse-riding session across scenic trails, followed by olive picking (in season) or learning about traditional farming techniques.
Lunch is a hearty, homemade affair using ingredients from the estate—freshly pressed olive oil, hand-rolled pasta, seasonal vegetables, and locally raised meats. Children can interact with animals, while adults can unwind under the shade of old olive trees.
ET Recommends: Make time for the olive oil tasting and cheese-making workshop—fun, informative, and deeply local.
Day 5: Florence – A Renaissance Treasure Trove
While the countryside is restful, no visit to Tuscany is complete without a day in Florence. Begin with Michelangelo’s David at the Accademia Gallery, then explore the Uffizi with a family-friendly guided tour that brings Renaissance masterpieces to life. Stroll across the Ponte Vecchio and marvel at the Duomo’s architectural perfection.
Couples may enjoy a private art walk through the Oltrarno neighbourhood or a sunset aperitivo at Piazzale Michelangelo, with panoramic views over the terracotta rooftops.
ET Recommends: Take a short detour to Fiesole for lunch with a view, followed by a quiet walk through Roman ruins and peaceful olive groves.
Day 6: The Castelfalfi Experience & a Tuscan Farewell
End your journey with a blend of nature, gastronomy, and leisure at Castelfalfi—a restored medieval hamlet turned sustainable luxury estate. Here, you can choose between a romantic Vespa tour through the vineyards, a truffle hunt in the woods, or a cooking class using ingredients from the estate’s organic gardens.
Children can participate in kid-friendly workshops or enjoy the open-air pool and adventure trails. For adults, the estate’s spa and golf course offer time to unwind and reflect.
ET Recommends: Book a farewell dinner at La Rocca, Castelfalfi’s fine dining restaurant set in the village’s castle tower—elegant, local, and deeply atmospheric.
What makes Tuscany special isn’t just its beauty—it’s how that beauty unfolds slowly, rewarding those who take the time to look. Six days here allow you to soak in the culture, connect with the land, and enjoy meaningful moments—whether you’re on a romantic escape or travelling with loved ones.
At Eastern Travels, we believe Tuscany is not just a destination—it’s a lifestyle worth living, if only for a few perfect days. Let us tailor your journey, from handpicked stays and exclusive tastings to hidden hamlets and bespoke experiences that go far beyond the postcard.