One of the larger Italian hilltop towns in the Tuscany region, San Gimignano is truly a star. Named an UNESCO World Heritage site for its Medieval style, its charm is easily found in the historic buildings and small alleyways.

As you walk into town, stretching up the steep streets to the main square, you feel immediately transported back in time. With it being a small town, you can walk the town to take in the sights. It also features a highlight — the world’s best gelato shop. Let’s just say we may have gone twice.

The city could be easily reached by a day trip from Florence, however staying near the city is an absolute treat as it affords you the opportunity to see it early in the morning before the crowds and at night when it lights up.

What and Where: San Gimignano, Italy Guide

Where to Stay in San Gimignano

  • Villasanpaolo Resort and Spa: This hotel just outside the city, is a great spot to call home while exploring the region. With an onsite spa and pool, it is relaxing after a long day of adventure. Read the full review here.

Where to Eat in San Gimignano

  • The world’s best gelato at Gelateria Dondoli: it truly is amazing.
  • Fattoria San Donato: This was a highlight, where we ate in the dining room of the owners, in a family style setting. This agriturismo farmhouse serves a dinner using their own ingredients, wine made on property and let you experience eating a true Tuscan meal.
  • Poderi Arcangelo: Another option for agriturismo dining.
  • Cum Quibus: a high-end Italian restaurant with Mediterranean flare.
  • D!Vineria: Stop by for a glass of wine and small plates.
  • Caffe Giardino: A good spot for lunch with local dishes.

What to Do in San Gimignano

  • Checkout the main square named Piazza del Duomo.
  • Head out of town to wine taste, at favorites like La Roccaia Winery, Tenuta Torciano, and Vernaccia.
  • Walk to the top of one of the towers to take in the views, with the most popular being the Torre Grossa.
  • Try local products like boar salami, pecorino, and wine.
  • Checkout the Collegiate Church of San Gimignano.
  • Take a road trip around the area to see the neighboring towns and landscape.
  • Take a road trip to Chianti, here’s a one day guide.

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