Getaway Compass

Top 5 Tuscan Towns You Must Visit

These 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, potentially addictive gelato, and wine you can drink like apple juice from a juice box (it’s just that good).

1. Montepulciano

Montepulciano View

A dreamy Tuscan town perched on a hill, Montepulciano will steal your heart. This town 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. If you want to spend a night in a Tuscan town this is the one that I would recommend. There are many airbnbs where you can stay right in the town.

2. Volterra


Walk around this quiet and romantic Tuscan town with beautiful views. 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


A small town in in the middle of Val D’Orcia, Pienza is worth a quick stop for a glass of wine and cheese with views of the rolling hills. You don’t need more than 30 minutes to see the entire old town, but you can always spend more time relaxing and enjoying the views.

4. Montalcino


A quiet Tuscan town in Val D’Orcia known for its Brunello wine. This is the perfect town to relax, drink wine, and have lunch (just remember to eat lunch early because almost everything closes at 3!)

5. San Grimignano

San Grimignano

A very popular medieval hill town known for its fourteen watch towers, San Gimignano 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.

Disclosure: Please note that some of the links above are affiliate links for products and services I recommend. At no additional cost to you, I earn a commission if you make a purchase. As an Amazon Associate I earn from qualifying purchases.

Reut and Zack Elopement-5

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