There are so many amazing little towns to explore throughout Tuscany and deciding which one is no easy task – we landed on San Gimignano largely because of our time constraints (we only had the weekend). And well, it’s pretty darn picturesque. However, it is an itty bitty town so there aren’t loads of things to do within the city walls so we ventured out to a local winery and we were not disappointed!

How We Got There:

From the station in Florence, we were able to catch a bus straight to San Gimignano. Getting back ended up being a bit of a debacle after our hotel inaccurately relayed the Sunday bus schedule to us and we missed the last bus out of San Gimignano. Never fear though – as a couple had pulled over in front of the bus stop to struggle with their navigation I asked if they’d give us a ride to Poggibonsi (from there we were able to get a train back to Florence). Long live hitch hiking!

Where We Stayed: 

Found via Air B’n’B, we stayed in an old family home in the heart of the city. No frills, but was an absolutely beautiful building.

What We Did:

Meandering. As you do. It’ll only take you a couple hours to meander through every little street, passageway, and piazza.

Photo Opps. There’s a little scenic spot with amazing panoramic views off the main boulevard (the top photo). Breathtaking, really!

Picnic-ing. After a little struggle to find an actual grocery store (Hint: it’s outside the city walls), we assembled a veg, cheese, and meats spread and found ourselves a lovely bench outside the city walls overlooking the rolling Tuscan hills.

Tenuta la Vigna. Hello, wine tasting! About a thirty minute stroll down a dusty little road, my friend found this little gem by simply browsing Google maps. Not your typical, commercialised big wine tasting room, Tenuta la Vigna is a small family owned winery where my friend and I had a private wine tour with one of the cousins, Claudio, which ended up lasting hours. Timing was perfect with two of the other cousins (twins, in fact) bringing in the last of the harvest. We were shown the wine making process and strolled through the vineyards picking table grapes and apples whilst sipping our wine. Heaven? Pretty much.