Montevarchi(Italy) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Montepulciano, the top choice for authentic Tuscan charm is Agriturismo La Vigna, a restored 19th-century farmhouse nestled in the rolling hills of Tuscany. Guests enjoy homemade breakfast featuring local pecorino cheese, cured meats, and fresh bread, while evenings often include starlit wine tastings among vineyards.

Another standout is Villa Poggio del Sole, a serene retreat with private pool and ancient Roman-style courtyard, just a 10-minute walk from the historic town center. Both properties emphasize sustainability, using regional materials and organic ingredients. Staying here offers more than accommodation—it’s a full immersion into the rhythms of rural Tuscany life.

The heart of Montepulciano lies in its historic center, where cobbled streets and Renaissance-era facades create a timeless atmosphere. Must-visit spots include Chiesa della Madonna Assunta and Piazza Cavour, the vibrant square hosting weekly farmers’ markets offering handmade ceramics, olive oil, and local wines.

Just a 15-minute walk north leads to Cantina del Chianti, an underground winery where guided tours reveal the art of crafting classic Chianti Classico. This immersive experience connects visitors directly to the region’s winemaking heritage and culinary traditions.

Stay in the historic center of Montepulciano, such as Hotel Il Palazzo or B&B Villa Romana, both located within walking distance of Chiesa della Madonna Assunta and Piazza Cavour. From here, buses and rental cars make it easy to reach Pienza, Siena, and the Chianti wine region.

Many accommodations offer private driver services or bicycle rentals, ideal for exploring scenic country roads and hidden vineyard estates. The central location ensures convenience, safety, and quiet nights—perfect for travelers seeking both accessibility and authenticity.

Must-try experiences in Montepulciano include attending the Festa del Chianti, held annually in summer, featuring street dancers, live music, and stalls serving aged Chianti Classico and roasted suckling pig.

Join a local pottery workshop led by artisans, where you’ll craft your own traditional Tuscan ceramic piece—perfect as a souvenir. For food lovers, book a family-style cooking class to master dishes like wild mushroom risotto and tomato-based pasta using regional ingredients. End the session with a shared dinner of your creations, embodying the Italian tradition of food as love and connection.

Ristorante La Terrazza, perched on the old city walls, offers panoramic views and exceptional Tuscan cuisine. Signature dishes include truffle pork ragù pasta and slow-roasted lamb with rosemary potatoes, paired with curated Chianti Classico wines sourced from nearby vineyards.

Another gem is Osteria del Borgo, a tiny, intimate spot tucked in the old town alleyways. With only 12 tables, it features a Michelin-recognized chef who reimagines classic recipes. Try the black truffle risotto and beetroot salad with goat cheese, enjoyed beneath a century-old olive tree in a secluded garden setting.

The rolling hills around Montepulciano are perfect for hiking and cycling. Try the Via di San Michele trail, starting near Chiesa della Madonna Assunta, a 4km path through vineyards and oak forests with sweeping views of the Valley of Pienza.

There’s also a mountain biking route leading to the village of Acquaviva, ideal for intermediate riders. Spring and autumn offer ideal weather—mild temperatures and golden light. Many guesthouses rent bikes and organize sunset rides, stopping at ancient castles and family-run farms for wine and snacks, blending adventure with the beauty of Tuscany’s countryside.