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  • Writer's pictureVal Malecki

Journey Back in Time to the Old-World Town of San Gimignano!

You don't want to miss this amazing walled city with its narrow alleyways and ancient architecture. Along its narrow, winding streets you'll find shop after shop filled with all of Italy's best foods, wine, ceramics, leather goods, wood items and so much more!

Simply put, you can spend an entire day in San Gimignano, appreciating the beautiful weather, marveling at its medieval architecture, and taking hundreds of pictures of the locals enjoying espresso at one of the local restaurants.

As you meander through the town, you'll find a vast array of stores and restaurants, from souvenir shops, to fine Italian leather goods including handbags and shoes, and even specialty Italian foods. In one of the local restaurants which had maybe two tables total, we ordered the most amazing Charcuterie plate with meats, cheeses, and a truffle honey that was to die for.

San Gimignano even has its own fresh Pecorino cheese, which rivals the famous one from Pienza. You can choose pasta, meats, and local olive oil for your lunch or dinner. In the Piazza del Duomo, you can climb the stairway leading to the doorway of the Church of Collegiate. It is amazing to see such historic buildings still standing today, even though they were built before the Renaissance. Across the square it's a must to stop for a mid-morning espresso or a scoop of gelato. One of the local gelato stores has a sign that states, "The Best Ice Cream in the World," in perfect English. And after tasting it, I fully agree. Espresso and gelato is a must for anyone traveling in Tucany.

At the center of Piazza della Cisterna, you'll find a beautiful wishing well which is another amazing photo opportunity. In this main square, we came across a group of older Italian men sitting in a circle of chairs simply talking and enjoying themselves. You can experience what it's like to be submerged in the Tuscan culture. San Gimignano is so much more than just a tourist attraction, it's a place to view the lives of the local Italians.

After a full day of sight-seeing in San Gimignano, it's a pleasure coming back to

Totally Tuscany Villas, where you'll find a large chef’s-style kitchen, fully equipped so that you can create a wonderful Tuscan meal. After dinner, you can retire to your loggia (terrace), to end your day watching the sun set over the Chianti hillside while you sip a glass of vino.

The question is what to do tomorrow: maybe Lucca, Pisa, Montepulciano or even Cortona. There are so many adventures awaiting you during a vacation in Tuscany.

As the rental agent in the U.S., I look forward to helping you create the Tuscany experience of your dreams. I hope that you visit our website at and look into the possibility of making it your once-in-a-lifetime vacation.


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Ask us about our Personalized Tour Packages that offer you luxury amenities, the best tour guides, upscale private bus transport, an enthusiastic tour leader, a gourmet meal daily, and full admission to all museums and venues. There are no worries, no long lines, and we take care of everything to ensure a vacation of a lifetime!  Click here to discover customized tour packages.


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Tuscany is one of the most beautiful places on Earth to celebrate the joining of two individuals, whether it's your first wedding, a second marriage, a vow renewal, or a special anniversary! At our property, we have several beautiful locations overlooking the Tuscan hillsides where you can hold the ceremony and reception.  Click here to discover how we can help you create the wedding event of your dreams.

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