Five Tuscan Hill Towns Too Beautiful To Be Believed


Good evening, everyone! This week’s post is all about a handful of Tuscan hill towns that are way too gorgeous for their own good. Since I’ve already written about Siena and Cinque Terre they will not be included in this list, but just remember that I still carry a torch in my heart for each of them. And to be honest, they’re well-known enough on their own. If you’re staying in Florence for more than a few days, I highly recommend making a day trip out to one or two of these towns, especially since the regional trains are so ridiculously cheap (we’re talking 7-10 euros depending on the destination). I do want to make it clear that there isn’t “much” to do in any of these towns, so if you’re the kind of person who absolutely must have every moment taken up with activity then you should give them a pass. If you’re a born wanderer like me,  these towns will resonate in your soul long after you’ve left.

1. Cortona

I haven’t been to Cortona in three years, but it was one of my favorite parts about my second trip to Tuscany. I don’t even remember where I first heard its name, but it immediately caught my attention because it sounds like a destination in a pirate-themed movie or a video game. Say it with me: Uncharted 5, the Treasure of Cortona. Copyright Kelsey Clifton. Anyway, to get to Cortona you travel by train, and then you have to take a bus to the town because it’s at the top of a large hill. I mean, walk it if you want, but the bus is only a few euros. If I remember correctly, the correct bus stop is out of the station and to the left, but use your brain and look around. Better yet, if a bus does come, just point to the town up high and ask, “Cortona?” Add in a smile and you’ll be irresistible.

Once you get off the bus, immediately run over to the walls and check out that incredible view. Takes your breath away, right? I was drawn equally to the view and the steep, winding streets full of discoveries. Oh, and the nutella and orange gelato; I was also definitely drawn to that. There’s a central piazza with a clock tower and a church, and on that particular day I witnessed the tail-end of a Scottish wedding. I had no plan and was in no hurry, so I spent the next few hours pleasantly absorbing the beauty around me.


2. San Gimignano

Pronounced “jim-ih-nya-noh,” the Town of Fourteen Towers is a well-known sight in Tuscany. The towers were originally created as a way for the wealthy families in town to one-up each other; at one time there were 72 of them, each taller than the one before until the town council put an end to their shenanigans. Just over a dozen remain, but they’re incredibly well-preserved and I believe that you can go inside a few. I was there on a tour, so unfortunately I didn’t have enough free time to wander and wait in line. We came in on a tour bus, but a bit of research revealed that you need to go to Siena first and then take a bus to San Gimignano. More information (actually a whole frickin’ lot of information) can be found at There’s also an amazing free app for iPhones and Androids.

San Gimignano’s main square is the gorgeous Piazza della Cisterna, which centers around the well that used to be the town’s primary water source. It’s surrounded by buildings from a variety of periods, including one that houses the world gelato champions from 2006-2009. If they’re still around, you should definitely stop in for a scoop or three. Or four, no one’s judging. My activity in the town was limited that day by time and the rain pouring down on us, but it certainly didn’t stop me altogether. The biggest lesson I learned that day is that sometimes life is going to rain on you, and when it does you have two choices: you can either huddle under a shelter with everyone else, or you can go eat gelato in the rain. Guess which one I chose? And no, you don’t get a prize for guessing right, because come on. Gelato.


3. Lucca

I missed Lucca on my first two trips to Tuscany, but I got to visit back in June and it’s absolutely delightful. While still considered a hill town, it was the flattest of any of the ones that I visited and therefore easy on the legs. It’s a short train ride from Florence to Lucca, and once you exit the station just keep heading straight until you see the almost perfectly intact medieval walls. One of my favorite activities was exploring these walls in depth; there are so many great old nooks and crannies to discover, and the combination of old stone and greenery made for a fun time. The buildings inside the old town are just as lovely, and I recommend stopping by Chiesa di San Michele in the piazza that shares its name. Out of all the places on this list, Lucca might have been my objective favorite (objective because other towns hold certain memories that give them unfair advantages).

Another thing that you absolutely have to do is go to the top of Torre Guinigi. It’s this amazing tower with a rooftop grove of olive trees and incredible views of the town. It’s a fairly long climb up to the top, but so very, very worth it! For the full impact, keep your eyes down until you reach the railing. From the roof you’ll have an unobstructed view of the surrounding countryside as well as Lucca itself.


4. Arezzo

If you arrive in Arezzo by train, you can exit the station and walk straight ahead to make it into the main part of town, or take an immediate right on Via Roma once you reach the equilateral green space (Piazza Monaco) if you’d like to swing by the Roman Amphitheater. When I visited, there were several modern art displays around town, including white figures climbing the walls and mannequins with umbrellas hanging from cords. While the entire city is gorgeous, the diva of Arezzo would have to be Piazza Grande—it’s one of the loveliest medieval squares that I’ve ever seen. The steps of Chiesa S. Maria della Pieve create a grand stage from which to observe the colorful piazza and its beautiful residents.

Situated behind Arezzo’s Duomo is my favorite part of the city: il “Prato,” the gardens beneath the Medici Fortress. This incredible green space is a fantastic step back from streets and buildings, and it has three distinct styles within the same area. An open, well-maintained middle lawn gives plenty of room for games and picnics; the lower end is romantic with its windswept pines and views of the Tuscan countryside; and the end closest to the Medici Fortress is like a traditional park that’s been allowed to grow wild.


5. Campiglia Marittima

I have less information about arriving in Campiglia Marittima than the other towns because I visited by car with friends, but apparently there are frequent trains from Florence as well as buses. It might be in your best interest to travel by car, or at least to rent one while you’re in town, because one of the best draws is the seaside less than twenty minutes away. We visited two beaches in as many days, and though they weren’t as stunning as those you can find in the south, they’re definitely worth a visit. The first beach had extremely sparkly sand and a snack shack with alcohol, ice cream, and absolutely incredible Mediterranean Cous-Cous (PRO TIP: Get it with the tuna). Beach #2 lacked the fun sand, but more than made up for it with an incredible picnic area in the shade of the pine trees, where we drank beer and danced to a reggae band.

The town itself is ridiculously steep, but gorgeous. We spent most of our time down at the beach or up in our rented house, but we did wander down into town for dinner one night and breakfast our last morning. There are a few tiny piazzas and plenty of winding streets for wandering, not to mention an unparalleled view of the the countryside and the water. During August there’s Apriti Borgo, a medieval festival that goes on in the town center; while I arrived the day that it ended, I’ve been told that it’s a lot of fun to attend. Be aware that during this time it will cost money to enter the limits of the festival unless you’re staying in that area.

DSC_0507DSC_0534DSC_0543Happy wandering, my pets!

Pasta kisses,





About kclifton5

So for those of you who don't know the prologue of this story, here are the basics: three years ago I studied abroad in Hull, England and I traveled pretty extensively while I was on this side of the world. I fell in love with Italy and vowed that I would come back one day to try my hand at living there. Thanks to the actual Best Mom in the World, this hazy dream became a very firm reality back in May when I moved to Florence. I get a lot of questions about my decision, but the main one is very simple: Why? Because I wanted to be somewhere else for a while. It blew everyone's minds that I didn't have a job lined up already, and I didn't know anyone in Florence. Their eyes would widen and they would say, "Oh my God, that's brave!" Crazy. They mean it's crazy. But I'm alright with that, because I think life is more fun with a bit of crazy thrown in to spice things up.

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