A Unique Guide to Tuscany

Tuscany is one of those places that many of us dream of seeing at least once in our lifetime. Sun-drenched hills, charming villas and friendly people who will feed you until you feel like you’re going to burst— it’s the dream right? Well that vision of Tuscany is one to see, for sure, but there is much more to this wine-soaked region than the usual Italian cliches and postcard-perfect fields. Whether it’s theatrical flair or oddball attractions you’re looking for. Tuscany is one part of the world that truly delivers, as you will see below…

Yes, You Still Have to See the Leaning Tower (But Do It Right)

Look, you can’t come to Tuscany and skip Pisa. It’s touristy, it’s crowded, and yes, it really does lean. But once you’re done snapping the obligatory photo of yourself “holding it up,” do yourself a favor and actually go inside. While everyone else is outside trying to get the angle right, you could be climbing the tower or exploring the nearby Baptistery, which is oddly underrated. Pro tip: snag your Pisa Baptistery tickets in advance unless you enjoy standing in line while slowly melting under the Tuscan sun.

Go Where the Grapes Are, but Not Like Everyone Else

Tuscany is wine country, but you don’t have to follow the masses to the same over-hyped vineyard offering wine “experiences” that cost more than your flight. Instead, explore the lesser-known towns in Chianti or Val d’Orcia. Look for a tiny cantina with zero curb appeal and a grandma pouring wine out of a plastic jug. That’s the good stuff. It might not come with a sommelier, but it will come with a story—and maybe a homemade biscotti or two.

Hit the Hill Towns Before Your Legs Give Out

Tuscany is full of gorgeous hill towns, which is code for “prepare to climb things.” San Gimignano, Montepulciano, and Volterra all offer charm, stunning views, and that specific kind of calf workout you didn’t know you signed up for. Wander the cobbled streets, pop into random artisan shops, and try not to buy yet another bottle of truffle oil you’ll never use.

If you’re lucky, you’ll stumble into a local festival you didn’t plan for but will be glad you found. Bonus points if there are parades with costumes or donkeys involved.

Get Weird with Your Museums

Florence is packed with art, but if you’ve seen enough crucifixions and marble nudes to last a lifetime, mix it up on your next trip. Visit the Museo della Tortura (yes, a museum of torture devices), or seek out one of the smaller, weirder exhibitions in a tucked-away palazzo. Art is everywhere in Tuscany, and sometimes it’s hiding behind an espresso bar or under a gelato shop.

Wrap Up with a View (and a Gelato)

End your day the way Tuscans intended: sitting somewhere scenic with a scoop of gelato that’s technically your third of the day. Look out over a vineyard, a medieval tower, or just the chaos of a piazza filled with people all trying to look effortlessly Italian.

And if your only real achievement was not falling off a Vespa, well, that’s still a win in Tuscany.