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There is truly something magical about Tuscany. It is the kind of place where you picture yourself learning to make fresh pasta with a nonna, sipping wine down cypress tree lined roads, and wandering into medieval churches that have seen more centuries than you can count. While almost every corner of this region is gorgeous in its own way, today I want to share five of the most unmissable towns to visit in Tuscany and hopefully inspire you to add them to your own itinerary.
How We Made It Here
One of life’s great joys is when your friends get married. And no, I’m not talking about the whole love and vows part, although that is lovely. I’m talking about when they choose a destination wedding. Nothing says “I adore you” quite like being forced to hop on a plane to Italy, Mexico or Bali. What a hardship.
A few years ago, one of my close high school friends got married in Italy. And while it technically wasn’t a destination wedding, (she was marrying an Italian winemaker) it still felt like one. A very dreamy one. It was the perfect excuse for my husband and me to plan our first European adventure together. It wasn’t my first time in Europe, but it was his, which meant I was determined to make it epic.
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My Personal Travel Style
This trip was also when I shifted how I travel. In college, I bounced around from city to city with friends, trying to cram in as much as possible. London to Barcelona to Rome to Amsterdam all in one go. At the time, it felt iconic. But later I realized how chaotic and surface level it all was.
Now I travel by region. Instead of hopping between five countries in two weeks, I pick one area and deep dive. For example, during one trip we road tripped on the Wild Atlantic way in Ireland, tested tons of great pubs and historical sights in Dublin, kissed the Blarney Stone in Cork and even put our toes in the ocean in Donegal. I may have never been to Murder Hole Beach (more on this beach here) or had time to explore the Gap of Dunloe or the Ring of Kerry if we had just popped over to Ireland for a couple days, while (likely) never making it out of the capital.
Traveling this way makes everything feel richer. Driving small roads, chatting with locals, discovering tiny towns you never would have considered before. You spend less time sitting at airports and more time experiencing the actual country. Plus, if you are a type A Capricorn like me, this style feels extremely satisfying. So many boxes checked in one area.
Of course, there is zero shame in bopping from country to country if that’s your thing. But if you have a long trip coming up, whether it is a national park road trip or backpacking through South America, slowing down and focusing on one region is absolutely worth trying.
Tuscany
Alright, back to Italy. My friend was getting married near a small town called La California on the Tuscan coast, so we decided to make a full adventure out of it. We started in Rome and then spent ten days road tripping through Tuscany before ending the trip with Lake Como. It was cute, it was busy, and we saw some truly incredible places. Here are my favorites and why they are my most unmissable Tuscan spots.
Pienza
This list isn’t technically ranked by favorites, but if it were, Pienza would win. Nestled in the Val d’Orcia, this UNESCO World Heritage Site has such an interesting backstory. It was originally known as Corsignana and belonged to the Piccolomini family before Aeneas Piccolomini was born. He later became Pope Pius II and decided to rebuild the entire town in Renaissance style as his personal escape from Rome. Pope Pius was definitely giving main character energy, long before it we had a label for it.
Pienza still carries that history in its bones. It is genuinely one of the most beautiful towns we visited in Tuscany. The historic streets are filled with little shops, and every corner feels photogenic. Locals decorate their doorways with plants, flowers and ceramic pieces that make the whole place feel cared for.
Don’t miss the Cathedral in Piazza Pio II with its striking Gothic exterior. My personal favorite stop was Palazzo Piccolomini, the Pope’s former summer residence. When you step into the cloister, pale beige curtains hanging between white columns, looking out at a quiet garden, it feels like stepping into another century.
And of course, Pienza is the home of pecorino. If you smell cheese before you see it, congratulations, you are doing Pienza correctly.
Montalcino
A quick drive from Pienza brings you to Montalcino, also in the Val d’Orcia. This hilltop town has been settled since Etruscan times and still carries a medieval, slightly dramatic energy that I adored.
You can see most of Montalcino in a few hours, which makes it perfect for road trippers. The highlight is the 14th century Fortress where you can walk the courtyard, climb the tower and explore the outer walls. The views are unreal. You get sweeping panoramas of the rolling Tuscan countryside in every direction.
Montalcino is also the holy land of Brunello wine. This is one of Italy’s most iconic (and pricey) wines, made from 100 percent Sangiovese. We loved our tasting at Il Palazzone, where we learned about the wild rules for Brunello DOCG production. Wear good shoes though. This town sits on a hill, and some of the climbs are no joke, especially in summer heat.
Siena
Siena is more of a city than a town, but the impact it left on me earns it a spot on this list. The historic center is a UNESCO World Heritage Site and has deep ties to banking history. It is home to Monte dei Paschi, the oldest bank in the world, founded in 1472. You also might know Siena for its famous Palio horse races that take place twice a year in Piazza del Campo. Each rider represents one of the city’s 17 districts, and the whole event is a full spectacle.
If you visit in July or August, you may catch the Palio decorations and celebrations filling the square. The flags of each district transform the city into something that feels theatrical and deeply local.
Even without the Palio, there is so much to do. My favorite experience was climbing the Torre del Mangia, built between 1338 and 1348. It is narrow and the 505 steps will make you question your life choices, but the views at the top are worth it. Afterward, wander over to Siena’s stunning cathedral. Fun fact: it is intentionally the same height as the tower to symbolize that the church and state held equal power. The façade alone is unforgettable.
Montepulciano
About 40 minutes from Montalcino sits Montepulciano, home of Vino Nobile di Montepulciano (more delicious red wine). This medieval and Renaissance town sits high on a giant limestone ridge, which makes the views some of the best we experienced in Italy.
Montepulciano has been fought over throughout history and later became a sort of training ground for Renaissance architects, including Antonio da Sangallo the Elder. Today, it is a gorgeous place to wander and get “lost” among honey colored alleys and sweeping lookouts.
The main square, Piazza Grande, is home to the Cathedral of Santa Maria Assunta and Palazzo Contucci. And of course you should go wine tasting. Enoliteca Consorzio Vino Nobile is a great stop because they have glass floors where you can look down into an old stone wine cellar. It feels very secret passageway chic.
If you can time it right, stay for sunset. The hills glow gold, and you may have a spiritual experience.
Volterra
The last town on this list is Volterra. And yes, I fully stopped here because of the second Twilight movie. Zero shame. But honestly, I found a town even better than the Edward-and-Bella saga made it seem.
Volterra was once one of the main cities of the Etruscan Federation and still has sections of its ancient fortification walls dating back to the 4th century BC. Today, the town is known for its Roman ruins, medieval squares and its beautiful alabaster carvings.
Start your visit in Piazza dei Priori, surrounded by grand medieval palaces. Then wander through town imagining yourself running through the crowd in a red cloak during St. Marcus Day. Twilight fans get it. Don’t miss the Roman theater ruins and take time to enjoy the local wine and restaurants. Volterra feels both ancient and cinematic all at once.
The Bottom Line
You really cannot go wrong anywhere in Tuscany. The vineyards, rolling hills, medieval towns and centuries old traditions make this region endlessly enchanting. A few places still on my list that I have heard amazing things about include Orvieto, Lucca and San Gimignano. I hope you get the chance to explore this magical region, let me know how it goes.
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