Small towns in Tuscany for a quiet, slower trip (4 local favorites)

May 22

Tuscany is easy to recognise. The light, the colours, the cypress trees lining the roads just outside towns like San Quirico d’Orcia or Pienza. But once you’ve been to Florence or Siena, you start to realise how much of the region actually happens elsewhere: in the smaller towns that rarely make it onto a first itinerary.

Places where mornings start at the local bar, not in a queue. You stand at the counter, order a caffè, maybe a cornetto, and within a few minutes the same handful of people drift in - builders, shop owners, someone picking up bread before work. It’s quiet, but it feels lived in.

Around midday, things shift. Shops close, chairs get pulled in, and the pace changes without anyone really talking about it. In towns like Montisi or Radicofani, you’ll notice it straight away! Streets that felt gently busy in the morning go still for a while, and the only real option is to slow down with it.

That’s where Tuscany starts to feel different.

You don’t need much of a plan here. A short walk through the centre, maybe along Via principale or out towards the edge of town where the views open up. A coffee that turns into a glass of wine without much thought. A small alimentari where you pick up pecorino, bread, and something sweet for later.

If you’re looking for that version of Tuscany (the one that feels easy to settle into, even if it’s just for a couple of days) these four towns are a good place to start.

If your idea of a good day in Tuscany is a quick coffee and moving on, this probably isn’t for you.

But if you’re the kind of person who ends up staying longer than planned (finishing your espresso, ordering something small to eat, watching the same few people pass through the square) then these places will make sense.

The towns here are all within easy reach of Florence or Siena. You can get there without overthinking it. But once you arrive, the pace shifts quite quickly. Fewer people, fewer plans, more of that in-between time where nothing much is happening, but you don’t feel the need to fill it.

If you’re planning to move between towns without renting a car, this is worth a quick read first.

Cortona, Tuscany: A Quiet Hilltop Town with Views Over Val di Chiana

Cortona sits above the Val di Chiana, around an hour from Florence. The easiest way to get there is by train to Camucia-Cortona, followed by a short taxi ride or the local bus up the hill. If you’re driving, the road up from the valley is straightforward, with parking just outside the old town walls.

Most people come for a few hours, but it works better if you stay a bit longer.

If you want a view, you don’t need to go far. Walking towards Porta Bifora or up in the direction of Basilica di Santa Margherita opens things up quickly. The valley below is visible from several points, especially once you get slightly outside the centre.

The beauty of Cortona lies in its simplicity. The town is a maze of narrow cobblestone streets, ancient stone buildings, and rustic piazzas that exude the authentic Tuscan atmosphere. As you wander through the alleys, you’ll notice the distinct Tuscan architecture - the kind of old-world charm that makes it feel like stepping back in time. Each corner offers a new perspective, whether it’s a colorful flower box hanging from a window or a small artisan shop tucked away down an alley. It's the kind of place where you can easily lose track of time, and that's exactly the point.

Start your day with a visit to Caffè Tuscher, a local favorite that sits right in the heart of Cortona. With its cozy ambiance and a terrace that overlooks the rolling hills of Tuscany, it’s the perfect spot to enjoy a rich espresso or a creamy cappuccino. The best part? You’re surrounded by the gentle buzz of local life with people greeting one another, friends catching up over coffee, and the occasional dog lazily strolling by. If you’re lucky, you might even get a warm breeze carrying the scent of freshly baked croissants from the café’s kitchen.

Once you’re properly caffeinated, take a short walk to Piazza della Repubblica, the town’s lively main square. Here, you’ll find beautiful medieval architecture, and it’s the perfect spot to just sit, people-watch, and soak in the local atmosphere. You’ll notice the local shops selling handmade goods, fresh produce, and Tuscan wines. Don’t run through this part, take time to explore some of the little shops around the square. Le Botteghe di Cortona, for example, is a small artisan shop that’s known for its unique leather goods, perfect for picking up a keepsake.

From the square, make your way down Via Nazionale, a peaceful street lined with cozy boutiques, art galleries, and local eateries. As you walk, you’ll notice the scent of truffles wafting through the air. It’s a reminder that the Tuscan countryside is full of hidden culinary treasures, and Cortona is no exception. There’s something magical about wandering these quiet streets, where every corner you turn reveals a new local gem.

For a peaceful and reflective experience, take a gentle climb up to the Santa Margherita Sanctuary, located just outside the town center. This quiet spot is not only a place of spiritual significance but also offers some of the most breathtaking panoramic views in Tuscany. From here, you can see the entire valley, dotted with vineyards, olive groves, and charming farmhouses. It’s the perfect place to take a moment, breathe in the fresh Tuscan air, and appreciate the beauty of the landscape that stretches before you.

If you're feeling a bit more adventurous, head to Parco delle Rimembranze, a park that offers scenic walking trails just outside the town. It’s a great place for a leisurely stroll, and as you walk, you'll be surrounded by cypress trees and olive groves. The peacefulness of this park is perfect for those looking for a quiet, nature-filled retreat.

When it comes to dining, you can’t miss Osteria del Teatro, a small but incredibly charming restaurant tucked away in Cortona’s medieval heart. The atmosphere here is warm and intimate, and the food is as authentic as it gets. The menu features a wonderful selection of Tuscan dishes, and the homemade pappardelle with wild boar ragù is a must-try. It's rich, hearty, and embodies the essence of the Tuscan countryside. If you’re in the mood for something lighter, the fresh bruschetta with ripe, sun-kissed tomatoes and basil is a perfect choice.

If you’ve saved room for dessert (and you definitely should), don’t miss the cantucci with Vin Santo. These traditional almond biscuits are the perfect way to end any Tuscan meal, especially when paired with a glass of Vin Santo, a rich dessert wine made locally. The sweet and nutty flavors of the cantucci dipped in the wine will leave you with a lingering taste of Tuscany that will make you wish you could stay just a little longer.

For a slightly different perspective on Cortona, make sure to visit the Museo Diocesano. The museum is home to some stunning religious art and provides insight into the town’s history. It’s a quieter spot compared to the bustling squares and streets, and it’s a great place to appreciate Cortona’s deep-rooted cultural significance.

If you’re planning to stay a little longer, you’ll find plenty of accommodations that offer that quintessential Tuscan charm. Villa di Piazzano, a stunning 16th-century villa turned boutique hotel, is just a short drive from the town center. The views from the hotel are as gorgeous as the villa itself, and it’s a perfect place to unwind after a day of exploring. Alternatively, if you prefer a more intimate experience, there are also charming guesthouses tucked in the rolling hills around Cortona, offering peaceful escapes with stunning views.

If you like the idea of building a trip around smaller towns like this, this one shows how to do it by train over a weekend without overcomplicating things.

Cortona has a calm, easy feel to it. The streets are quiet, the views are always close by, and there’s no real sense of urgency. It’s somewhere you can just take your time without thinking too much about what to do next.

Pienza, Tuscany: A Small Town Known for Pecorino and Valley Views

Pienza sits in the Val d’Orcia, between Montepulciano and San Quirico d’Orcia. It’s easiest to reach by car, especially if you’re already exploring the area. If you’re relying on public transport, the closest train station is Chiusi-Chianciano Terme, followed by a bus or taxi, which takes around 30–40 minutes.

Once you arrive, everything is within walking distance.

The town is small and built around Corso il Rossellino, the main street that runs through the centre. Along here, you’ll find several pecorino shops like Marusco e Maria and Caseificio Cugusi, where locals and visitors stop in to taste or pick up cheese to take away.

Pienza is the kind of town that feels like it belongs to another era! A place where history, art, and nature blend seamlessly together. Known as the "Ideal Renaissance Town," it was reimagined in the 15th century by Pope Pius II, who wanted to create a perfect model of urban planning. As you wander through its cobbled streets, you’ll quickly understand why this small town, with its Renaissance charm, has earned its place on UNESCO’s World Heritage list. And the best part? Unlike many Tuscan towns, Pienza remains refreshingly free of overwhelming crowds, which gives it a special, almost timeless feeling.

One of the best ways to start your visit to Pienza is with a quiet morning at Caffè Etruria. Tucked into the main square, this cozy café is beloved by locals, making it the perfect place to enjoy a pastry and a coffee while soaking up the town’s peaceful atmosphere. The outdoor terrace offers a lovely view of the surrounding landscape - think rolling hills dotted with olive groves and fields that seem to stretch endlessly into the distance. It’s easy to lose track of time here, sipping your coffee as you watch the world go by. If you’re lucky, you’ll catch sight of the town’s residents heading off to work or stopping for their own morning ritual. This is the true essence of Pienza: calm, charming, and genuine.

If Pienza is your kind of place, there are a few other Tuscan villages with a similar feel that are just as easy to spend time in.

Once you’ve enjoyed your coffee, head to Piazza Pio II, Pienza’s main square. This beautiful space is the heart of the town, surrounded by impressive historical buildings, including the Palazzo Piccolomini (a grand Renaissance palace that was once home to Pope Pius II’s family). The piazza is a perfect place to linger, whether you’re watching the locals going about their day or simply enjoying the serenity of the surroundings. There’s no rush here, and that’s one of Pienza’s greatest gifts: the ability to just be present.

If you’re an art lover, take a moment to step inside Pienza’s Duomo (Cathedral of Santa Maria Assunta), which sits proudly in the middle of the square. While the church’s exterior is stunning, it’s the interior that really takes your breath away. The simple, unadorned design is a testament to Renaissance architecture at its finest, with beautiful frescoes and a sense of peacefulness that invites contemplation. It’s one of those places where you can simply sit and absorb the beauty around you, allowing the quiet of the church to wash over you.

And then, of course, there’s the main reason many visitors come to Pienza: its famed pecorino cheese. The town is known for producing some of the finest pecorino in Tuscany, and no visit would be complete without tasting this rich, tangy delight. La Bottega del Cacio is the place to go for a fresh slice of pecorino. This small, family-run shop is full of local cheeses, oils, and Tuscan products, and the staff is more than happy to share the history of the cheese and how it’s made right here in Pienza. You can sample a few different types and even pick up some to take home with you. If you want to enjoy the pecorino like a true local, pair it with some honey or fig jam - a classic Tuscan combination.

If you find yourself craving more of Pienza’s authentic charm, take a gentle walk to Pieve di Corsignano, a peaceful church located just outside the town center. This hidden gem offers a quiet retreat from the town’s main square and provides a beautiful vantage point of the surrounding landscape. As you walk the short distance from Pienza, you’ll find yourself surrounded by the rolling hills of Val d’Orcia, which is renowned for its unspoiled beauty. The church itself is simple yet serene, and it’s a wonderful spot to reflect or simply take in the view of the olive orchards, cypress trees, and sprawling fields that characterize the Tuscan countryside.

After your peaceful walk, you may want to spend some time exploring the area’s surrounding countryside. Val d’Orcia is an absolute highlight, known for its golden fields, distant hills, and iconic cypress-lined roads. If you have the time, rent a bike or just take a nice drive through the valley to experience the full beauty of the landscape. The hills are dotted with small farmhouses and vineyards, and each bend in the road seems to offer a new, stunning view.

For a truly authentic experience in Pienza, consider stopping by Enoteca di Pienza, a wine shop offering some of the best local wines. While you’re there, ask for recommendations and sample a glass or two of Rosso di Montalcino or a Vino Nobile di Montepulciano. Both of which come from nearby vineyards and are perfect accompaniments to your pecorino cheese. The shop’s owners are happy to provide recommendations, and you’ll leave feeling like you’ve discovered a new favorite wine that perfectly captures the essence of Tuscany.

If you’re looking for a place to stay, Pienza has a range of cozy, rustic accommodations that offer the perfect mix of comfort and character. For a true Tuscan experience, consider staying at La Bandita Townhouse, a charming boutique hotel located just outside of the town center. With stunning views over the Val d’Orcia, an inviting atmosphere, and beautiful design, it’s the perfect home base for exploring this peaceful corner of Tuscany.

Pienza is the perfect place to slow down and savor life at a gentle pace. From sipping coffee in the square to enjoying local cheese and wine, it’s the kind of town where you can experience the simple pleasures of Tuscany. And with its history, art, and stunning landscapes, you’ll leave feeling like you’ve stepped into a place where time slows down just enough to enjoy everything it has to offer.

If you’re planning your trip around food as much as place, this gives a good overview of what’s in season across different parts of Italy.

And if you’re heading further north at any point, Bologna is one of the easiest cities to experience that slower, food-focused way of travelling.

San Gimignano, Tuscany: What It’s Like Beyond the Crowds

San Gimignano is an easy one to reach if you’re already in Florence or Siena. Most people go via Poggibonsi and then take the short bus up the hill. If you’re driving, you just park outside the walls and walk in.

You’ll see the towers before you get there. They stand out straight away, especially compared to other towns nearby.

It does get busy in the middle of the day, mainly around Piazza della Cisterna and Piazza del Duomo. That’s just how it is. But if you get there earlier, or stay a bit later, it feels completely different.

In the morning, it’s still quiet. Places like Gelateria Dondoli are just opening, and you can walk through the streets without needing to move around people. Later on, once things calm down again, it’s easier to slow your pace and actually look around a bit.

If you walk a few streets away from the main squares, it changes quickly. Even just heading along Via San Giovanni or out towards Rocca di Montestaffoli gives you a bit more space.

It’s not a hidden place, but it doesn’t need to be. You just have to time it right…

Start your visit with a quiet morning at Bar La Cisterna, a local favorite tucked in one of the town’s quieter corners. Here, you can enjoy a classic Italian breakfast of espresso or cappuccino paired with a pastry, all while taking in the views of the surrounding countryside. The café has a relaxed vibe, making it the perfect spot to sit back, enjoy your coffee, and watch the town slowly wake up. The peaceful atmosphere here is the perfect introduction to the rest of your day, setting the tone for a slow, unrushed exploration of San Gimignano.

After your coffee, take a stroll through the town’s charming cobblestone streets. San Gimignano’s old town is a maze of narrow alleys, quaint shops, and open piazzas. The medieval architecture here is beautifully preserved, giving you a genuine sense of what the town must have looked like centuries ago. You’ll pass by old stone walls adorned with creeping vines and doorways that seem to invite you in to discover the secrets hidden behind them.

A must-see stop is the Collegiate Church of Santa Maria Assunta - a peaceful, historic church located in the heart of the town. Stepping inside, you’ll be greeted by beautiful frescoes that date back to the 14th century, telling stories of biblical events in vibrant colors. The church’s serene ambiance provides a welcome break from the bustling streets outside, and it’s a perfect spot to pause, reflect, or simply admire the artistry of the past.

San Gimignano is also known for its delicious gelato, and no visit would be complete without a stop at Gelateria Dondoli. This place has been serving up some of the best gelato in Tuscany for decades, and for good reason. The flavors are inventive and authentic, with options like saffron, honey and almond, and even chocolate with truffle. It’s a treat you won’t want to miss, especially as you take your cone and wander through Piazza della Cisterna, one of the town’s most picturesque squares. The square is surrounded by tall medieval buildings, and its peaceful atmosphere is the perfect setting to sit and enjoy your gelato. If you’re visiting during the late afternoon, you’ll find the golden light of the setting sun casting a warm glow over the piazza, making it feel like a scene from any Tuscan movie.

If you’re drawn to the views around San Gimignano, the Prosecco Hills have a similar mix of walking routes and open landscapes, just in a slightly different setting.

And if you’re more into combining that with short hikes, this goes a bit deeper into the trails in that area.

San Gimignano is a town that’s easy to fall in love with! Not just because of its historical significance, but because of the slow, calm pace it offers. And while San Gimignano does attract tourists, it still holds onto a sense of authenticity and quiet, especially if you explore it in the early morning or late afternoon when the crowds have cleared.

If you're interested in a bit more history, the San Gimignano 1300 Museum is an excellent stop. It offers a detailed, miniature-scale replica of the town as it looked in the 14th century, which gives a fascinating perspective on how the town has evolved over time. The museum is housed in a medieval building, and it provides a nice, calm alternative to the more crowded areas of town.

Piazza della Cisterna, the square where Gelateria Dondoli is located, is one of the town's most iconic spots. It's not only picturesque, but it’s also home to several medieval towers, some of which were once part of wealthy families' homes. These towers are a hallmark of San Gimignano’s skyline, and you can still climb to the top of some of them for breathtaking views of the Tuscan countryside. The climb to Torre Grossa, the tallest of the towers, is well worth it for the panoramic views of the surrounding hills and vineyards.

For a quiet break from sightseeing, you can also visit Villa San Paolo, a peaceful hotel on the outskirts of San Gimignano that offers sweeping views of the rolling Tuscan countryside. It’s an excellent spot to unwind, enjoy a glass of local wine, and take in the beauty of the region at a slower pace.

If you're keen on taking home a piece of Tuscany, don’t forget to explore the small shops around town. San Gimignano is famous for its hand-painted ceramics, and you’ll find plenty of shops selling unique pottery and local crafts. Another great souvenir is Vernaccia di San Gimignano, a white wine made from grapes grown in the surrounding vineyards. Many local wineries offer tastings, so if you're a wine enthusiast, it's worth stopping by one of the nearby estates for a taste.

San Gimignano is one of those towns that offers a perfect blend of history, charm, and tranquility. It may be known for its towers, but it's the peaceful moments (like enjoying a gelato in the piazza, exploring its cobblestone streets, or soaking in the panoramic views) that truly make it special. If you’re looking for a quieter experience of Tuscany, without sacrificing beauty or culture, San Gimignano is the perfect destination.

If you’re travelling with a friend rather than solo, this gives a slightly different angle on quieter Italian towns that work well for a more relaxed few days together.

Lucignano, Tuscany: A Small Circular Village That’s Easy to Miss

Lucignano sits between Arezzo and Siena, slightly off the main routes, which is probably why it feels quieter than a lot of other towns in this part of Tuscany. It’s easy to reach by car, and there’s parking just outside the walls. If you’re using public transport, the closest station is Sinalunga, followed by a short taxi ride.

The first thing you notice is the layout. The streets form a series of tight circles that slowly lead you towards the centre, rather than the usual straight roads you find in most towns. You don’t really need a map here — you just keep walking and eventually end up back where you started.

Everything is close together. A few small cafés, local shops, and quiet corners where not much is happening. If you walk towards Piazza del Tribunale, you’ll reach the centre of the village, where the pace feels even slower.

Start your day at Caffè Italia, a welcoming café located just off the main square. With its outdoor seating, you can sip a cappuccino or an espresso while gazing out at the town’s charming surroundings. The café has a relaxed vibe, and it’s the perfect spot to take a slow moment before you begin exploring Lucignano’s vibe. Enjoy the quiet rhythm of local life, whether it’s the sound of a dog barking in the distance or the occasional car driving by. This is the essence of Lucignano: simple, serene, and unhurried.

Lucignano is known for its unique golden tree - a stunning piece of medieval art that is housed in the town’s Museum of Lucignano. The golden tree is a symbol of the town’s history, and the craftsmanship behind it is truly remarkable. The museum itself is a small but fascinating place to learn about the town’s past, from its medieval roots to its evolution over the centuries. While the museum is definitely worth a visit, the best part of Lucignano is the time you can spend simply wandering through its streets. The town’s circular design means you’ll always end up back at the main square, giving you a sense of discovery and tranquility as you take your time exploring.

One of the things that makes Lucignano so special is its incredible local food. This isn’t a place overrun with tourist traps or overpriced menus - instead, you’ll find authentic Tuscan eateries that serve up delicious, home-cooked meals made from fresh, local ingredients. A perfect example is Ristorante Il Goccino, a cozy, unpretentious spot where you can enjoy traditional Tuscan fare in a relaxed, welcoming atmosphere. The restaurant is famous for its tender beef stew (perfect for chilly evenings) and handmade pasta, which is rich and full of flavor. The menu changes with the seasons, so you’ll always get a taste of whatever is freshest and most local. The quiet, intimate setting of Il Goccino makes it the ideal place to savor the slow flavors of Tuscany without the distraction of busy crowds.

If you’re looking for a peaceful escape into nature, take a short walk to Parco della Rimembranza, a beautiful park located just outside the town center. The park is a wonderful place to get lost in the quiet of Tuscany’s countryside. Surrounded by trees and lush greenery, it’s the kind of spot where you can take a cozy stroll, sit on a bench, and just breathe in the fresh air. The park is well-maintained, and the serenity of the space makes it easy to forget the outside world. It’s a perfect place to enjoy some solitude, reflect on your time in Lucignano, or simply enjoy the beauty of the region at a slower pace.

For those who love a bit of history and culture, Lucignano’s medieval walls are a must-see. The town is encircled by these well-preserved walls, which have stood the test of time. You can take a walk along the walls or explore the city gates, which are great for photographs or simply admiring the architecture. As you wander, you’ll notice how well the town has maintained its charm. Unlike other Tuscan towns, Lucignano doesn’t feel like it’s trying to be a tourist attraction… it’s simply itself, with all its natural beauty and historical richness on full display.

If you’re interested in local crafts, be sure to stop by one of the artisan shops around the town. Lucignano is known for its handmade ceramics, and you’ll find several shops where you can pick up a unique souvenir to take home. The ceramics are colorful and beautifully made, showcasing the traditional techniques passed down through generations. Whether it’s a simple bowl or a decorative plate, these pieces are a perfect way to bring a piece of Tuscany back with you.

The best part of Lucignano is the fact that it hasn’t yet been spoiled by mass tourism. While the larger Tuscan towns like Florence and Siena may attract the crowds, Lucignano offers an experience that feels untouched by time. It’s the kind of place where you can unwind, enjoy great food, and simply be in the moment.

If you’re looking for a place to stay, Hotel Il Belvedere is a wonderful option. Located just outside the town’s historic center, the hotel offers comfortable rooms with stunning views of the Tuscan countryside. It’s a peaceful retreat after a day of exploring the town, and its proximity to Lucignano means you can easily return to the town for evening walks and dinner.

Lucignano is the kind of town you’ll want to keep for yourself - a local gem that offers a glimpse into Tuscany’s authentic charm. The town’s peaceful atmosphere, rich history, and local flavors make it a perfect destination for those looking to experience Tuscany without the crowds.

If you like this slower pace, there’s a similar kind of trip just outside Rome, in the Sabina Hills.

How to Actually Enjoy These Tuscan Towns (Without Overplanning It)

The easiest way to get more out of places like Cortona, Pienza, San Gimignano, and Lucignano is to keep your plans light once you arrive.

Start earlier than you think. In most of these towns, cafés open around 7:30–8:00. If you’re out then, you’ll catch that short window before day visitors arrive - especially in places like San Gimignano. Order a simple coffee at the bar, stand for a few minutes, and watch the town wake up. It’s a completely different experience than arriving mid-morning.

Around 12:30–14:30, things slow down. Smaller shops close, and lunch takes over. Instead of trying to fit things in, it’s easier to follow that rhythm. Sit down somewhere, order something local (in Pienza, pecorino with honey or jam is easy to find), and give it time.

If you want quieter streets, don’t stay on the main routes. In Cortona, stepping away from Via Nazionale makes a big difference within a minute or two. In San Gimignano, even one street back from Piazza della Cisterna is noticeably calmer.

A small practical thing that helps: wear proper shoes. The streets are steep, uneven, and mostly stone. You’ll walk more than you expect, and it’s much easier when you’re not thinking about your feet.

If you’re driving, park outside the walls and leave the car there. Most of these towns have limited access inside, and it’s easier to explore everything on foot. Distances are short, but the layout can feel slower because of the hills and narrow streets.

Staying overnight changes everything. Even one night means you get the early morning and late evening, which are easily the best times to be there.

And if your day ends up being nothing more than a walk, a coffee, and somewhere to sit for a while, that’s usually a good sign.

FAQ: Planning a Slower Trip in Tuscany

What does a slower trip in Tuscany actually look like?

It usually means planning less once you’re there. Instead of moving between sights all day, you base yourself in one or two towns and build the day around simple things such as a morning coffee, a walk through town, a long lunch, maybe a short drive in the afternoon. Most places don’t need a full itinerary to make sense.

Which small towns in Tuscany are quieter but still worth visiting?

Cortona, Pienza, San Gimignano (outside peak hours), and Lucignano are all easy to reach and don’t require much planning once you’re there. They’re small enough to walk, have a few good places to eat, and enough going on without feeling busy all day.

When is Tuscany at its quietest?

May, early June, and late September tend to be the easiest times to travel without crowds. July and August are much busier, especially in places like San Gimignano. If you’re visiting in high season, early mornings and evenings make a big difference.

Do you need a car to visit these towns?

It helps, but it’s not always necessary. Cortona can be reached by train (Camucia-Cortona) and a short taxi ride. San Gimignano is usually reached via Poggibonsi and a bus. Pienza and Lucignano are easier with a car, especially if you want to move between towns without checking timetables.

How long should you stay in each town?

Half a day is enough to see most of them, but staying overnight changes the experience. You get the quieter hours (early morning and late evening) which are often the best parts of the day.

What should you actually do during the day?

Keep it simple. Walk through the centre, stop for coffee, sit down for lunch somewhere local, and leave time to wander without a plan. In Pienza, that might mean trying pecorino in one of the small shops. In Cortona, it could just be sitting near Piazza della Repubblica for a while.

Where should you eat in small Tuscan towns?

Look for places that are already busy with locals around lunchtime, usually between 12:30 and 14:00. Short menus are often a good sign. In smaller towns, you don’t need to over-research - a simple trattoria in the centre is often enough.

Where is the best place to stay for a slower trip?

Staying just outside a town or in a smaller village nearby often works well. Agriturismos in the countryside give you more space and quieter evenings, while staying inside towns like Pienza or Cortona makes it easy to walk everywhere.

What’s one mistake people make when visiting Tuscany?

Trying to fit too much into one day. These towns are close together, so it’s tempting to visit several in one go. It usually works better to pick one or two and spend more time in each.

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