GemmaIf you’re a lover of wine, history, or just breathtaking scenery, the area around Montepulciano in Tuscany is like stepping into a dream. Nestled among rolling hills, endless vineyards, and medieval architecture, this region doesn’t just offer wine—it offers an experience. From my own personal experience, the villages surrounding Montepulciano are gems that are often overlooked by travelers who stick only to the main town. But once you venture off the beaten path, you’ll find charm, tradition, and flavors that will stay with you long after you leave.
Let me take you on a tour of 12 charming wine villages around Montepulciano, each offering something unique—from must-see sights to unforgettable tasting experiences. Whether you’re a seasoned traveler or planning your first Tuscan adventure, these villages will leave you inspired, entertained, and maybe just a little tipsy in the best way possible.
1. Pienza – The Renaissance Gem
Pienza is often called the “ideal Renaissance town,” and for good reason. It was redesigned by Pope Pius II in the 15th century to reflect the ideals of urban planning and beauty. Walking through its streets feels like stepping into a painting—cobblestone alleys, pastel-colored buildings, and panoramic views of the Val d’Orcia valley.
Things to do here include visiting the Palazzo Piccolomini, enjoying local pecorino cheese at the shops lining the central square, and sipping a glass of Rosso di Montepulciano while soaking in the view. Pienza isn’t just about sightseeing; it’s about savoring the atmosphere. From my overall experience, the sunsets here are unforgettable, painting the valley in gold and pink hues.
2. Monticchiello – A Medieval Retreat
If you crave authentic medieval charm, Monticchiello is your village. Perched atop a hill, this tiny town has kept its ancient walls and narrow streets almost intact. It’s perfect for a slow stroll, where you can admire stone houses adorned with flowers and discover small artisan shops.
Things to do here include exploring the Teatro Povero, a community theater that stages performances reflecting local life and traditions, and tasting wine at one of the family-run cellars. You’ll also love the quiet serenity—Monticchiello has that rare, timeless feel where the pace of life seems gentler, allowing you to truly soak in Tuscany’s magic.
3. Chianciano Terme – Relax and Unwind
Chianciano Terme is known for its thermal baths, but there’s more than just wellness here. The village sits amidst lush hills and vineyards, making it ideal for wine lovers who also enjoy relaxation. The thermal waters are said to have healing properties, and after a day of wine tasting, a soak here feels like heaven.
You can explore the Museo Civico Archeologico for a touch of history, wander the botanical gardens, or simply enjoy a glass of Vino Nobile di Montepulciano at a local terrace overlooking the valley. Trust me, combining wine and wellness has never felt so luxurious.
4. Montelpulciano Stazione – The Gateway to Wine Country
Though smaller and less picturesque than the hilltop town of Montepulciano itself, Montelpulciano Stazione is where the modern meets the traditional. The charm here is understated: a central square, small trattorias, and local wine shops.
It’s an ideal starting point if you’re planning vineyard tours, as many wine estates are just a short drive away. From my personal experience, stopping here for a casual lunch of fresh pasta and local wine gives a different, more relaxed perspective compared to the bustling hilltop village.
5. Trequanda – Rolling Hills and Rustic Charm
Trequanda is one of those villages that feels untouched by time. The views of the surrounding vineyards are stunning, and the village itself is filled with quiet streets and historic churches. The Castello di Trequanda offers insight into medieval life, and wandering around its stone walls feels like stepping into a storybook.
Wine here is less commercial but incredibly flavorful, with small wineries producing wines you won’t find on tourist lists. Exploring Trequanda gives you a sense of discovery, a chance to experience Tuscany like a local.
6. Sarteano – History and Wine in Perfect Harmony
Sarteano offers a rich mix of history and viticulture. Archaeological sites hint at ancient settlements, while vineyards produce some of the best local wines. The village is also home to charming cafes and restaurants, perfect for tasting traditional Tuscan dishes alongside a glass of Rosso di Montepulciano.
One of the highlights here is the Sarteano Castle, offering panoramic views of the surrounding countryside. From my overall experience, the combination of historical exploration and wine tasting here is unmatched—an ideal way to spend a leisurely day.
7. Trevinano – Hidden Wine Treasure
Trevinano is a small village that often flies under the radar, but it’s perfect for travelers looking to escape the crowds. Vineyards surround the village, and local winemakers are eager to share their craft. You can taste wines straight from the barrel, paired with homemade bruschetta or fresh cheeses.
Walking through Trevinano’s quiet streets, you’ll feel like you’ve stumbled into a secret corner of Tuscany, one that feels intimate and authentic.
8. Montefollonico – A Hilltop Delight
Montefollonico sits high on a hill, offering stunning panoramic views of the Tuscan landscape. The village is famous for its medieval architecture and winding streets that invite exploration. Local wineries here often welcome visitors for tasting sessions, where you can learn about traditional wine-making techniques.
It’s also a photographer’s paradise—sunsets cast golden light over terracotta roofs and vineyards, creating that iconic Tuscan postcard scene. You’ll truly fall in love with Montefollonico if you appreciate charm in every corner.
9. Cetona – Art, Culture, and Wine
Cetona combines cultural richness with vineyard beauty. The village has narrow streets filled with art galleries, artisan shops, and cafes serving traditional Tuscan fare. Wine lovers can explore nearby estates producing both red and white wines.
From my personal experience, Cetona is a perfect day trip: you can admire Renaissance architecture, enjoy art exhibitions, and finish the day with a glass of wine overlooking the hills. It’s a full sensory experience that’s hard to forget.
10. Chiusi – Etruscan Heritage and Vineyards
Chiusi is steeped in Etruscan history, with archaeological sites and museums detailing its ancient past. Vineyards surround the village, offering both beautiful scenery and exceptional wines. Exploring Chiusi is like combining a history lesson with a culinary adventure.
Things to do include visiting the Museo Nazionale Etrusco, strolling the historic streets, and sampling wines at local estates. From my overall experience, Chiusi is where history and wine seamlessly blend, creating a journey that’s both educational and indulgent.
11. Montenero d’Orcia – A Peaceful Wine Escape
Montenero d’Orcia is small but full of character. The village overlooks the Orcia valley, offering some of the most serene views in the area. Wineries nearby produce exceptional wines, often with family-run charm and personal stories behind each bottle.
You’ll love taking long walks along the hilltops, enjoying the quiet, and stopping at a local enoteca to taste wine paired with fresh bread and local cheese. It’s the kind of village that encourages slowing down and savoring life.
12. San Quirico d’Orcia – A Perfect Tuscan Village
San Quirico d’Orcia is a classic Tuscan village with medieval streets, historic churches, and beautiful gardens. The Horti Leonini gardens are a must-see, with symmetrical designs and views over the rolling countryside. Wine lovers can visit nearby estates producing both red and white varieties, many with tours and tastings.
From my own personal experience, the village is perfect for an afternoon stroll, discovering charming corners, and enjoying a glass of wine while taking in the panorama. It’s the perfect blend of culture, history, and viticulture.
Final Thoughts on Exploring Wine Villages Around Montepulciano
Venturing beyond Montepulciano itself opens up a world of charm, history, and wine that you can’t fully experience from the main town alone. Each of these 12 villages offers something special—whether it’s panoramic views, centuries-old architecture, or intimate wine tastings.
From my overall experience, the true magic happens when you take your time, wander through quiet streets, talk to local winemakers, and savor both the flavors and the stories behind each village. Tuscany isn’t just about wine—it’s about connection, discovery, and creating memories that linger long after your trip ends.
So, plan your visit, grab a map, and set off on an adventure through these wine villages. You’ll not only taste incredible wines but also experience the authentic heart of Tuscany in a way few travelers ever do.
I’m Gemma, a passionate lifestyle blogger sharing my creative world with you. Gemitaliano.com is my little corner of the internet, glad you’re here.