Tuscany, with its charming hill towns, breathtaking landscapes, and centuries-old architecture, is a true Italian gem that transports you back to medieval times.

Known for its Etruscan history and flourishing during the Renaissance, Tuscany's hill towns like Siena, Volterra, and San Gimignano are among the most picturesque and historic in Italy.

These towns are a perfect escape for those looking to enjoy Tuscany’s enchanting vibe, winding alleys, and views that stretch to forever. Let’s take a closer look at five must-visit hill towns where Tuscany’s heart beats strongest. If you have never been to Tuscany, this might be your sign!

1. San Gimignano: The Town of Towers

Famous for its impressive towers that once symbolized the wealth of rival families, San Gimignano is Tuscany’s answer to a medieval Manhattan. You’ll be enchanted as soon as you see its skyline. Wandering through Piazza della Cisterna, you’ll find beautiful shops selling locally-made saffron and Vernaccia, a crisp white drink you’ll only find here. Budget around €10 for the climb up Torre Grossa, the tallest tower, offering views that make every step worth it! As one of the most popular towns, San Gimignano is lively year-round, especially in summer​!

2. Volterra: Etruscan Roots and Alabaster Artistry

For a slightly quieter experience, head to Volterra, known for its ancient Etruscan roots and rich alabaster tradition. Volterra has a distinct charm with its old-world piazzas, and the Piazza dei Priori stands out as one of Tuscany's oldest public squares. Take a peek into the town’s Etruscan museum, which costs around €8 and houses fascinating artifacts. The vibe here is laid-back and authentic, perfect for those wanting a slower-paced Tuscan experience without the throngs of tourists​

3. Cortona: Under the Tuscan Sun

Thanks to "Under the Tuscan Sun", Cortona has become something of a celebrity among hill towns. Perched on a hillside, it boasts dreamy views over the Valdichiana. Cortona's medieval streets are ideal for strolling, filled with artisan shops, cafes, and cozy trattorias where you can get a meal for around €15. Don't miss the Museo Diocesano, housing masterpieces by artists like Fra Angelico. If you’re a fan of charming streets and a relaxed vibe, Cortona is the place!

4. Monteriggioni: The Fortified Jewel

Monteriggioni is a tiny, fortified town that feels like stepping into a fairytale. Built as a defense outpost by the Sienese, Monteriggioni’s medieval walls remain nearly intact. Here, you can walk along the walls for €4 and even try on medieval armor at the local museum - a fun experience, especially for families. The town square, flanked by ancient stone buildings, is an idyllic spot to sit and enjoy gelato. Monteriggioni’s intimate size means you can explore it in half a day

5. Pienza: Renaissance Beauty in the Val d'Orcia

Last but not least, Pienza is a hilltop town renowned for its Renaissance architecture and its picture-perfect streets. Known as the “Ideal City,” Pienza was redesigned by Pope Pius II to reflect humanist ideals. The town overlooks the Val d’Orcia, a UNESCO World Heritage site. Don’t miss the Palazzo Piccolomini, where €7 grants you access to the terrace with unforgettable views. Also, Pienza is the place to try pecorino cheese - a local delicacy you’ll want to bring home!

Exploring Tuscany’s hill towns feels like diving into a storybook, each town offering unique experiences from lofty towers to quiet fortresses. To make the most of your journey, be sure to carry cash, as many small shops may not accept cards. And remember, each town is on its own hill, so wear comfortable shoes! Happy travels!