Panoramic from top of garden staircase San Gimignano
Panoramic from top of the garden staircase in San Gimignano

This is the fifth installment in a seven-part series following JohnnyJet.com writer Cynthia Cunniff through her experience of touring Italy with Insight Vacations. Head back to the series home page for the full Italy experience—or jump straight over to Day 1Day 2Day 3Day 4Day 6 or Day 7 of the tour.


DAY 5

San Gimignano
On the second day at the villa (Borgo San Luigi) we took a day trip to San Gimignano, a Tuscan hilltop town with two fortress towers that represent the 12th-century warring families of the Guelphs and Ghibellines. Our guide Belinda led us past the towers, across the main square through serpentine alleys and up the back of the town into a walled garden. Along the far end of the garden was a narrow stone staircase that led up to a lookout with stunning views of the Tuscan countryside; below was a fruit orchard and winding paths.

Hilltop San Gimignano
Hilltop San Gimignano

I had to wonder if I could’ve found this piece of wonderful on my own, and concluded most likely not in the timeframe with which we had to visit San Gimignano. Belinda left us to stroll back into the main area of town of our own accord, or simply enjoy the local musician playing exotic wind instruments in the garden courtyard.

Mr. & Mrs. Dondoli at Gelateria Dondoli
Mr. & Mrs. Dondoli at Gelateria Dondoli

A highlight of our visit to San Gimignano was Gelateria Dondoli. Holy creamy cow—the mother of all gelato resides here. Sergio Dondoli is a world-renowned, prize-winning gelato master and, yes, there is a difference between your typical gelato and the deliciousness he produces. Dondoli is a farm-to-table type of guy, and the outcome is the silkiest of Tuscan flavors in unique combinations (a personal favorite is the saffron with pine nuts). Dondoli is also quite a character and is very happy to engage the masses that show up for his gelato in English or his native Italian. As with so many eateries in Italy, it’s about showmanship as much as it is about the food.

Orchard doorway
Orchard doorway

Tip:  There is a grocery store near where the bus will park in San Gimignano. This is a great opportunity to see how the locals shop and to pick up some inexpensive gifts—particularly for those that love to cook.

We ended up back at the villa to gear up for our bike ride through the rolling countryside to a winery, where we found a down-home, Mama-made dinner and lots of laughter. I was very grateful the bus was picking us up and we didn’t have to ride back in the dark, as I was loaded to the gills with homespun food and wine.

Bike ride through Tuscan countryside
Bike ride through Tuscan countryside

This is the fifth installment in a seven-part series following JohnnyJet.com writer Cynthia Cunniff through her experience of touring Italy with Insight Vacations. Head back to the series home page for the full Italy experience—or jump straight over to Day 1Day 2Day 3Day 4Day 6 or Day 7 of the tour.

Approaching San Gimignano
Approaching San Gimignano
Vineyard near San Gimignano
Vineyard near San Gimignano
Vineyard near San Gimignano
Vineyard near San Gimignano
Carlo, our talented and friendly bus driver
Carlo, our talented and friendly bus driver
One of the many unique stores in San Gimignano
One of the many unique stores in San Gimignano
Happy boar - San Gimignano
Happy boar - San Gimignano
Something tells me these guys know what they're doing
Something tells me these guys know what they're doing
View from San Gimignano
View from San Gimignano
Belinda with local baker
Belinda with local baker
Hilltop garden - San Gimignano
Hilltop garden - San Gimignano
Garden staircase view - San Gimignano
Garden staircase view - San Gimignano
Local musician - San Gimignano
Local musician - San Gimignano
Artistry at every turn in San Gimignano
Artistry at every turn in San Gimignano
Grocery store in San Gimignano
Grocery store in San Gimignano

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