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Tuscany is a whimsical maze of cypress-lined roads weaving through bucolic hills, and medieval towns dotting the hilltops among valleys filled with vineyards. Despite its fame and recognition, Tuscany truly is one of the most enchanting destinations on the planet. No matter how many tourists make the trip or how many movies romanticize the culture and landscape, Tuscany delivers every time. Much of the Tuscan character lies within its charming little towns, surrounded by impenetrable stone walls and built in the Middle Ages atop hills for maximum protection. For your next Italian adventure, here are Tuscany’s five best hilltop towns.

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Montepulciano

Montepulciano

Beloved for its velvety, terroir-driven wines and beautiful Renaissance architecture, Montepulciano is a don’t-miss stop for any Tuscan itinerary. Starting at the perimeter, visitors weave their way up its stony streets, passing leather-goods stores and gelato shops along their way. At the top, Piazza Grande, the impressive town square, is a wonderful place to relax and enjoy the bustling village life. For breathtaking views of the Tuscan landscape, climb to the top of the Palazzo Comunale’s bell tower. Bring your camera, because this corner of Tuscany is straight out of the picture books. Stay close by at the enchanting Montepulciano’s Etruria Resort & Natural Spa, housed in a carefully restored 1800 villa with beamed ceilings, a secret garden and perfect views of Montepulciano .

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Pienza

Set high within the stunning Val d’Orcia, Pienza became a beacon of Renaissance urbansim when Pope Pius II rose to power and turned his hometown in an idyllic city of the times. With his helping hand, one of the first urban master plans came to fruition. Now a World UNESCO Heritage Site, it’s one of the most picturesque and beloved towns in all of Tuscany. It’s also known for its deliciously savory Pecorino cheese, so be sure to stock up when you’re there. Enjoy a leisurely garden lunch at La Bandita Townhouse and rest your head at night at Relais Il Chiostro di Pienza., a historic property that maintains many of its original charms, and features vaulted ceilings and a rooftop terrace.

Scenery of Siena, a beautiful medieval town in Tuscany, Italy

Siena

Siena

Siena just might be the crown jewel of Tuscany. From the epic Piazza del Campo town square to one of the most jaw-dropping duomo’s in Italy, this medieval masterpiece should be high on any traveler’s bucket list. It is a center for art, architecture, culture and cuisine and offers a wealth of things to do for travelers of all ages. Twice a year in summertime, Siena explodes with excitement during their Palio di Siena, a wildly entertaining bareback horse race around the Piazza del Campo. During the race, 10 of the town’s 17 neighborhood (contrades) are represented, flaunting their colors and mascots as they vie to cross the finish line first. During your time here, let the Hotel Continental Siena be your home base.

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San Gimignano medieval town in Tuscany Italy

San Gimignano

San Gimignano

The hilltop town of San Gimignano is undeniably known for its tall towers. Centuries ago, prominent families displayed their wealth by building towers taller than their friends or neighbors. Now 14 towers in the hilltop town reach for the sky, but back in its prime, 72 towers created a Manhattan-like skyline in the middle of Tuscany. Charming medieval streets and an abundance of history define this unique outpost between Florence and Siena. To make an overnight stay of it, check out La Collegiata, a picturesque monastery-turned-hotel just outside of town.

View of the Tuscany city Cortona

Cortona

Cortona

Cortona‘s beauty was perfectly captured in the 2003 movie Under the Tuscan Sun, starring Diane Lane. While that film attracted many new visitors, Cortona has long been on the radar of Tuscan travelers. Nestled into the side of a hill, every spot in town seems to have a spectacular view of the countryside around. Spend the morning at Cortona’s cathedral, Museo Diocesano, then spend the afternoon visiting one of the area’s great wineries. The acclaimed Avignonesi winery provides one of the best vineyard experiences in Tuscany and lies about 15 minutes outside of Cortona’s walls. For a lovely stay in the area, check out Relais Il Falconiere, an elegant country estate with picture-perfect vistas and a world class spa.

Tagged: Europe, Italy

Compass + Twine
Sarah Driggs and Lindsay Ridenour are the story-tellers behind the NYC-based luxury travel blog, Compass + Twine. Follow along on Instagram @compassandtwine as they unearth some of the best hotels and travel experiences around the globe. From scenic landscapes to local cafés, they reveal the true character of a destination, always highlighting the best place to stay on compassandtwine.com .
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