Getaway Compass

5 Most Beautiful Towns in Tuscany

These five Tuscan towns will make you feel as though you are in your own version of Under the Tuscan Sun. You will fall in love with their medieval architecture, breathtaking views, delicious gelato, and world renowned wine. To truly experience the culture of the Tuscan town spend a night at a Airbnb in the town.

1. Montepulciano

Montepulciano View

Montepulciano is my favorite town in Tuscany. This dreamy Tuscan town is perched on a hill with beautiful views of surrounding vineyard. Montepulciano is known for the delicious Vino Nobile di Montepulciano and Rosso Di Montepulciano which you can enjoy at any restaurant or winery. With narrow streets, lots of local restaurants, small shops, and incredible views, Montepulciano is a must-visit. 

Walk to Piazza Grande, Montepulciano’s center where you will find the Cathedral and the clock bell tower. A visit to Montepulciano is not complete without climbing the clock tower to get a view of the town and the Tuscan Countryside, with Val D’Orcia and Val Di Chiana on either side. Spend a night in an airbnb right in the town to see what it is like to live in a Tuscan village.

2. Volterra


The romantic town of Volterra makes this list of the 5 most beautiful towns in Tuscany. This town feels like a dream, with breathtaking views of the countryside. Spend time walking around this quiet town and enjoy a relaxing glass of wine with a view.

Tip: Near parking number 1 pedestrian entrance there is an incredible view of the town and the surrounding vineyards (as seen in the above picture).

3. Pienza


Pienza is one of the most beautiful towns in Tuscany, located in the middle of Val D’Orcia. The best way to experience Pienza is with a glass of wine and cheese at a local restaurant while enjoying views of the rolling hills.

4. Montalcino


While in Tuscany, don’t miss the beautiful town of Montalcino which is known for its Brunello wine. This is the perfect town to relax, drink wine, and have lunch. Remember to eat lunch early because almost all restaurants are closed 3-6 pm.

5. San Grimignano

San Grimignano

A very popular medieval hill town known for its fourteen watch towers, San Grimignano is a great place to walk around and experience a busy Tuscan town. Recognized as a UNESCO World Heritage Site, it gets very crowded in the main areas but if you walk away from the main squares you can find quiet streets and views of the surrounding countryside. If you want to explore the most beautiful towns in Tuscany, San Grimignano can’t be missed!

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Reut and Zack Elopement-5

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