Not every place on this list is quiet. Not every one is “undiscovered.” Some are packed with people and overpriced gelato. Others are half-empty with cats sleeping in the streets.
But all of them — in one way or another — are worth seeing.
Because there’s something about Tuscany that stays with you. And it’s not just the views. It’s the feeling you get walking through a stone alley at the end of the day, when the tourists are gone and someone’s cooking dinner with the window open.
This list isn’t about ranking towns. It’s about the ones that left a mark — famous or not. The ones I’d go back to tomorrow.
Province of Siena
San Gimignano
San Gimignano is one of the most famous villages in Tuscany—and for good reason. Once called the “Manhattan of the Middle Ages,” it was known for its many towers. Today, only 13 of the original 72 remain, but they still give the town a magical skyline.
San Gimignano: What’s Actually Worth Your Time
- Torre e Casa Campatelli: Step inside this tower-house to see what life was like in the Middle Ages.
- Torre Grossa: This is the tallest tower in town—and yes, you can climb it! The view from the top is unforgettable.
- Duomo (Collegiate Church of Santa Maria Assunta): Don’t miss the stunning cycle of frescoes inside.
- Piazza della Cisterna: The heart of the village, lined with shops and two legendary gelaterie—Gelateria Dell’Olmo and Gelateria Dondoli (a two-time world champion).
- Parco della Rocca: A peaceful park with beautiful views—and it’s free!
- Rocca di Montestaffoli: Climb the walls of this ruined fortress for a sweeping panorama. Free entrance.
- Fonti Medievali: Hidden medieval fountains just outside the walls. Free and worth the walk.
Good Places to Eat in San Gimignano:
- Osteria del Carcere: No pizza, no pasta — just traditional Tuscan dishes like ribollita, wild boar stew, and pecorino with honey. Very local, very relaxed.
- Trattoria Rigoletto: Simple, well-priced, no-frills trattoria near the city gate. Locals eat here. Grilled meats and handmade pasta are solid.
San Gimignano Events and Festivals You Shouldn’t Miss
- Ferie delle Messi (June) This is the big one! Held every June, the Ferie delle Messi is a medieval harvest festival that transforms the town into a living history set. Locals dress in costume, knights parade through the streets, there are flag-throwing shows, music, markets, and traditional games. The atmosphere is incredible, especially in the evening when torches light up the stone alleys and piazzas.
- Estate Musicale (Summer) During the summer months, San Gimignano hosts open-air concerts—classical, jazz, folk—in historic settings like cloisters and piazzas. Some are free, others ticketed, but they all feel magical under the Tuscan sky.
- Calici di Stelle (August 10) Wine lovers, this is your night! On the evening of San Lorenzo, wineries open their doors, and you can taste local wines under the stars, with music and events scattered through the town.
These festivals can get busy, so if you’re staying overnight, book your accommodation early. And definitely bring your camera—the photo ops are endless.
Festival dates can occasionally change. For the most up-to-date information, check the official San Gimignano tourism website
Monteriggioni
Tiny but absolutely enchanting. I stumbled upon it by chance and was struck by its perfectly round walls (part of which you can now walk along), quaint piazza, and charming streets with elegant shops and weathered stone arches. Scenes from The English Patient, Stealing Beauty, and Gladiator were filmed here.
Monteriggioni: What’s Actually Worth Seeing Inside the Walls:
- Walk the Walls: A short section of the medieval wall is open to visitors. From the top, you get beautiful views of the countryside and rooftops below.
- Piazza Roma: The main square is small but full of charm. Grab a coffee, sit in the sun, and soak in the quiet beauty.
- Church of Santa Maria Assunta: A simple Romanesque church right in the square.
- Explore the Streets: There are just a couple of narrow streets, but they’re lined with artisan shops and stone archways—perfect for photos.
- Monteriggioni in Arme Museum: Small but interesting, with medieval weapons and armor you can try on. Great for kids or history fans.
Best Places to Eat in Monteriggioni
There are a few nice spots in the piazza, but if you want something truly special, consider timing your visit with a local festival like Monteriggioni di Torri si Corona—the medieval fair held in July, with food, music, and people in costume.
What Not to Miss in Monteriggioni (Even If You’re Just Passing Through)
If you’re visiting in summer, check if your trip coincides with “Monteriggioni di Torri si Corona”, the town’s famous medieval fair with costumes, music, and ancient games.
Montepulciano
This hilltop town captivated me completely. Walking up from the lower part of town to the magnificent Piazza Grande is a must. There, you’ll find the Duomo, the Town Hall, and two historic wine cellars—Contucci and de’ Ricci—where you can admire giant oak barrels aging the prized Vino Nobile di Montepulciano DOCG.
Things to Do in Montepulciano (Besides Just Drinking Vino Nobile):
- Climb the Town Hall Tower: It looks a bit like the one in Florence—and yes, you can climb it! The view over rooftops and rolling vineyards is stunning.
- Tempio di San Biagio: Just outside the walls, this beautiful Renaissance church sits surrounded by olive groves and cypress trees. The setting alone is worth the walk.
- Wine Tasting: Don’t leave without sampling Vino Nobile. Aside from Contucci and de’ Ricci, many enotecas offer free tastings—some even in underground caves!
Where to Eat in Montepulciano: A Few Spots That Are Actually Worth It:
Try Osteria Acquacheta for a hearty Tuscan meal. It’s famous for its giant steaks and rustic atmosphere, but reservations are a must.
A Few Things Not to Miss in Montepulciano (Even If You’re Just Here for the Wine):
- Bravio delle Botti (Last Sunday of August)
This is Montepulciano’s wildest and most iconic event! Eight districts (contrade) compete by pushing enormous 80kg wine barrels uphill through the steep streets of the historic center—all the way to Piazza Grande. It’s sweaty, loud, and incredibly fun to watch. The week before is full of processions, flag throwers, and open-air feasts.
Check dates each year, as the schedule may vary slightly. - Natale nel Borgo (December)
During the holidays, Montepulciano transforms into a winter fairy tale with lights, a Christmas market, and even a castle for children near the Medici Fortress. The atmosphere is cozy and festive—perfect if you love quieter, off-season magic.
Montalcino
Famed for Brunello wine, Montalcino feels like a fortress-town. Walk through its narrow lanes, see the towering Palazzo dei Priori, and of course, enjoy a tasting of the Brunello in one of the many wine shops or enotecas.
Montalcino: What’s Actually Worth Your Time While You’re There
- Fortezza di Montalcino: Climb the walls for the best view in town. Free to enter the courtyard, a small fee to access the walls.
- Civic and Diocesan Museum of Sacred Art: If you love Renaissance art, this small but refined museum inside the former convent of Sant’Agostino is worth a stop.
- Abbey of Sant’Antimo: A few kilometers from town, this Romanesque abbey is nestled in a silent valley. At certain times, you might hear Gregorian chants echoing through its stone walls.
Where to Eat in Montalcino: Good Food That’s Not Just About the Wine
Try Taverna del Grappolo Blu—a cozy, no-frills place loved by locals and visitors alike for its hearty Tuscan dishes and fair prices. If you’re after something more refined, Drogheria Franci offers a contemporary take on traditional cuisine, right near the fortress.
Don’t Miss: Festivals & Unique Experiences in Montalcino
- Jazz & Wine in Montalcino July 22–27, 2025 This beloved summer festival blends world-class jazz performances with the region’s renowned Brunello wines. Concerts are held in stunning venues like the medieval fortress and Castello Banfi, creating an unforgettable atmosphere. The 2025 lineup includes international jazz artists, promising a week of exceptional music and wine.
- Benvenuto Brunello February 14–17, 2025 This prestigious event marks the release of the new Brunello di Montalcino vintage. Wine enthusiasts and professionals gather to taste and celebrate the latest offerings from local producers. It’s a must-attend for those passionate about Italian wines.
- Sagra del Tordo (Festival of the Thrush) Last Sunday of October This traditional festival features medieval costumes, archery competitions, and a lively parade through the town. It’s a celebration of Montalcino’s history and culture, offering visitors a glimpse into its rich past.
Pienza
Once known as Corsignano, this was completely redesigned by Pope Pius II with architect Rossellino, following Renaissance ideals. Hence the new name: Pienza. The main street, Corso Rossellino, is lined with leather shops and cheese sellers (hence the delightful blend of scents).
Piazza Pio II is home to the Cathedral, Palazzo Piccolomini, and more. Don’t miss the panoramic view over the Val d’Orcia and the poetic street names like “Via dell’Amore,” “Via del Bacio,” and even “Vicolo Cielo.”
What’s Worth Seeing in Pienza (Other Than Every Single Street Corner):
- Palazzo Piccolomini: You can visit the interior, including the private rooms of Pope Pius II and the beautiful Renaissance garden.
- Il Duomo: The Cathedral may look simple outside, but inside it’s filled with light and elegant Renaissance details.
- Walk the Walls: The edge of town offers a peaceful stroll with benches, perfect for a sunset moment.
- Pecorino Tasting: Pienza is famous for its pecorino cheese, aged in caves, ash, or walnut leaves. Stop in one of the many tiny shops to try a few varieties.
Where to Eat in Pienza (Without Ending Up in a Tourist Menu Trap):
For lunch or dinner with a view, try La Porta in nearby Monticchiello or Trattoria Latte di Luna, just outside Pienza’s walls—friendly service, local dishes, and generous portions.
What Not to Miss in Pienza (Even If You’re Only Here an Hour):
- Pienza e i Fiori (May 3–18, 2025) Each spring, Pienza transforms into a vibrant floral haven during the “Pienza e i Fiori” festival. The heart of the town, Piazza Pio II, showcases a Renaissance-inspired garden, this year themed around Venus, the goddess of beauty and love. The event features floral displays, plant and flower fairs, musical performances, and cultural talks, all celebrating the harmony of nature and art
- Festa del Cacio (September 7, 2025) Celebrate Pienza’s renowned Pecorino cheese at the annual “Festa del Cacio.” The highlight is the traditional “Gioco del Cacio al Fuso,” where participants roll wheels of cheese in a spirited competition. The festival also offers cheese tastings, local delicacies, and a festive atmosphere that brings the community together.
- Pienza Music Festival (July 11–22, 2025) For classical music enthusiasts, the Pienza Music Festival offers a series of concerts featuring advanced violinists and violists. Set against the backdrop of Pienza’s historic architecture, the festival provides an intimate musical experience in a picturesque setting.
Monticchiello
Nestled in the rolling hills of Val d’Orcia, Monticchiello is a picturesque medieval village that offers a unique blend of history, culture, and community spirit. With its well-preserved stone architecture, winding alleys, and panoramic views, it provides an authentic Tuscan experience away from the typical tourist paths.
Monticchiello: What’s Worth Seeing in This Tiny Tuscan Village:
- Porta Sant’Agata: The main entrance to the village, this 13th-century gate is flanked by ancient towers and offers a glimpse into Monticchiello’s fortified past.
- Pieve dei Santi Leonardo e Cristoforo: This Romanesque-Gothic church houses remarkable 14th and 15th-century frescoes from the Sienese school, including scenes from the life of Saint Catherine of Alexandria.
- Cassero Fortress: Although in ruins, the remains of this 13th-century fortress provide a tangible connection to the village’s medieval history.
- Scenic Viewpoints: Monticchiello offers stunning vistas of the Val d’Orcia, with its iconic cypress-lined roads and rolling hills—a photographer’s paradise
Top Things Not to Miss in Monticchiello:
- Teatro Povero di Monticchiello: Every summer, the village of Monticchiello hosts the “Teatro Povero” (Poor Theatre), a distinctive theatrical experience where local residents write, direct, and perform plays that reflect their community’s history and contemporary issues. These performances, often termed “autodrammi,” take place in the village’s open-air theater, offering audiences an intimate glimpse into the life and spirit of Monticchiello. Teatro Povero di Monticchiello Late July to mid-August (exact dates vary annually)
Castiglione d’Orcia
Castiglione d’Orcia is a picturesque medieval village offering breathtaking landscapes, rich history, and authentic Tuscan charm. Perched on a hilltop, it provides panoramic views of rolling hills, vineyards, and olive groves.
Things to Do in Castiglione d’Orcia (Even If You’re Just Stopping for the View):
- Rocca di Tentennano: This imposing fortress dominates the village skyline. Dating back to the 13th century, it played a strategic role in controlling the Val d’Orcia. Visitors can explore its towers and enjoy sweeping views of the surrounding countryside.
- Sala d’Arte San Giovanni: Housed in a former oratory, this art museum showcases works by renowned Sienese artists, including Simone Martini and Giovanni di Paolo. It’s a testament to the village’s rich artistic heritage.
- Chiesa di Santa Maria Maddalena: A Romanesque church featuring a semicircular apse and a bell gable, reflecting 12th-century architecture.
- Chiesa dei Santi Stefano e Degna: The main parish church, known for its historical significance and architectural beauty.
- Bagni San Filippo: Just a short drive away, these natural hot springs are famous for their white calcium formations and warm thermal waters, offering a relaxing experience amidst nature.
Where to Eat in Castiglione d’Orcia (There Aren’t Many — But They’re Good):
- Trattoria Il Cassero: A cozy eatery offering traditional Tuscan dishes like pici pasta and wild boar stew, set in a rustic ambiance.
- L’Appalto: Known for its warm hospitality and local cuisine, this restaurant provides a genuine taste of the region.
- Taverna di Mozart: Set in a charming location, it offers a delightful menu combining classic and contemporary Tuscan flavors.
Castiglione d’Orcia Festivals and Events: What’s On and When to Go:
- Il Maggio (April 30 – May 1): A traditional festival celebrating the arrival of spring. Locals, known as “Maggiaioli,” sing folk songs throughout the village, bringing joy and good wishes for the new season.
- Calici di Stelle (August 10): Part of a nationwide event, this evening features wine tastings under the stars, celebrating the region’s renowned Orcia DOC wines.
- Sagra del Fungo e della Castagna (October): Held in the nearby village of Vivo d’Orcia, this festival honors local mushrooms and chestnuts with food stalls, music, and traditional games like the “Palio del Boscaiolo.”
Bagno Vignoni
Bagno Vignoni is a unique Tuscan village known for its ancient thermal baths, tranquil atmosphere, and scenic beauty. Unlike any other town in Italy, its main square is a large, steaming pool of thermal water, making it an unforgettable stop in the heart of the Val d’Orcia.
Bagno Vignoni: What’s Worth Seeing in This Tiny Spa Village:
- Piazza delle Sorgenti: At the heart of the village lies this 16th-century rectangular pool filled with naturally hot thermal water. Once frequented by pilgrims, popes, and nobles, it’s the defining feature of Bagno Vignoni and a perfect photo spot.
- Parco dei Mulini: A short walk downhill leads you to the “Park of the Mills” — a fascinating site with ancient stone mills powered by thermal water. Explore pathways, waterfalls, and views of the Orcia River valley.
- Church of San Giovanni Battista: Overlooking the thermal pool, this simple yet historic church has served the spiritual needs of visitors since the Middle Ages. It’s a peaceful place for reflection.
- Thermal Spas and Wellness Centers: While the main pool is for viewing only, several nearby resorts and wellness centers (like Adler Spa or Hotel Posta Marcucci) offer access to hot mineral-rich pools with panoramic countryside views.
Where to Eat in Bagno Vignoni (Yes, It’s Small — But You’ve Got Options):
- steria del Leone: A refined but relaxed spot serving classic Tuscan recipes like ribollita, truffle pasta, and locally sourced meats — all with a view of the steaming waters.
- La Bottega di Cacio: Part deli, part eatery, this cozy restaurant specializes in cheese-based dishes, charcuterie boards, and local wines. Don’t miss the pecorino di Pienza!
- Ristorante Il Loggiato: Set in a charming stone building with outdoor seating, this restaurant offers hearty Tuscan fare with vegetarian options and an excellent wine list.
A Few Things Worth Showing Up For in Bagno Vignoni:
- Festa delle Acque (June): A celebration of water and local heritage, featuring open-air concerts, guided walks along the mills, and cultural events celebrating Bagno Vignoni’s unique relationship with its thermal springs.
- Notte Romantica (Late June): Part of a national event celebrating Italy’s most beautiful villages (Borghi più belli d’Italia), the night features candle-lit dinners, music, and poetic atmospheres.
- Terme sotto le Stelle (August): Some wellness centers offer late-night spa access under the stars, often paired with aperitivo, light shows, or DJ sets — a modern take on a centuries-old tradition.
Why Bagno Vignoni Is Worth a Stop — Even If You’ve Seen a Dozen Tuscan Towns:
Bagno Vignoni isn’t just beautiful — it’s therapeutic. With its blend of thermal wellness, historic character, and scenic serenity, it offers a quiet yet unforgettable experience in Tuscany’s most poetic landscape.
Province of Florence
Certaldo
Certaldo is one of those places that quietly surprises you. Perched on a Tuscan hilltop, it’s a red-brick medieval village that feels frozen in time — but not in a staged or touristy way. It’s real. Locals still live here, hang their laundry from windows, and sip wine as the sun dips over the Val d’Elsa valley.
Best of all? You’ll probably have it mostly to yourself.
Certaldo: What’s Actually Worth Seeing While You’re There:
- Certaldo Alto: The upper town is the heart of it all. You can either walk up the hill or take the charming funicular (highly recommended if it’s hot). Once you arrive, you’ll find narrow brick alleys, terracotta rooftops, and views that stretch for miles.
- Palazzo Pretorio: This fortress-like building dominates the village skyline. Its facade is covered in ancient coats of arms — marks left behind by past governors. Inside, you can walk through old courtrooms, jail cells, and frescoed halls that whisper stories from centuries past.
- Casa di Boccaccio: This is where the famous author of The Decameron, Giovanni Boccaccio, lived and died. The house has been turned into a small museum and library. Even if you’re not into medieval literature, it’s worth a visit just for the view from the tower.
- Chiesa dei Santi Jacopo e Filippo: A peaceful Romanesque church tucked into the village — it’s also where Boccaccio is buried. The interior is simple but moving.
- Wander. Slowly. The real beauty of Certaldo is how unhurried it feels. Walk the old streets, peek into artisan shops, and just soak up the atmosphere. This is slow travel at its best.
Best Places to Eat in Certaldo: Simple Food, Good Wine, and No Tourist Menus:
- Osteria del Vicario: Upscale, but not pretentious. You’ll dine in a historic bishop’s residence with views for days. The food is seasonal, local, and full of soul.
- La Terra degli Uccellini: A rustic place where the dishes taste like someone’s nonna is still in the kitchen. Great house wine, hearty portions, and friendly faces.
- Ristorante A Casa Tua: Just what the name says — “At Your House.” Casual, cozy, and perfect after a long walk. Try the pappa al pomodoro or pici with ragù.
Don’t Miss: Festivals and Events in Certaldo That Are Actually Worth Going To:
- Mercantia Festival (July): For a few magical nights, Certaldo Alto turns into an open-air stage. Street performers, musicians, fire dancers — it’s creative, a little quirky, and completely unforgettable. If you’re planning a summer trip, time it for this.
- Boccaccesca (October): Part food festival, part cultural tribute to Boccaccio — this one is for the foodies. Local wines, cheeses, olive oil tastings, cooking shows, and more.
- Art Thursdays (Giovedì delle Arti): During the warmer months, Thursday nights mean live music, small markets, and artists setting up along the streets. It’s low-key and lovely.
What Makes Certaldo Different — and Why You Might Actually Remember It
Because Certaldo isn’t trying to impress anyone. It just is what it is — a beautifully preserved village, full of history and character, that somehow avoids the crowds. If you’re road-tripping through Tuscany and want a stop that feels genuine and a little under-the-radar, Certaldo delivers.
Montefioralle
Montefioralle isn’t a place you stumble upon — it’s a place you gently seek out. Just above Greve in Chianti, tucked among vineyards and olive groves, this tiny hilltop hamlet is officially recognized as one of I Borghi più belli d’Italia — and for good reason.
Time moves slowly here. The streets are cobbled, the doors hand-carved, and flower pots line every windowsill. It’s one of those rare places where you feel like you’ve stepped into a painting — and yet it’s real.
What to See and Do in Montefioralle:
- Walk the loop — slowly: Montefioralle is small. You can walk the entire circular path around the village in under 15 minutes — but don’t. Take your time. Every corner, archway, and stairwell seems made for quiet admiration (or a perfect photo).
- The Vespucci House: One of the stone houses here is said to be the birthplace of Amerigo Vespucci, the explorer who gave his name to America. Look for the small stone crest with a “V” carved above the door — that’s the one.
- Chiesa di Santo Stefano: The village’s little church is simple and intimate, with faded frescoes and a peaceful atmosphere. It may not be grand, but it’s genuine — like the rest of Montefioralle.
- Enjoy the silence: There’s no real “main square” and no tourist bustle. That’s the charm. It’s quiet, local, lived-in. You might hear birdsong, a Vespa in the distance, or a neighbor sweeping their doorstep.
Best Places to Eat and Drink in Montefioralle (It’s Small — But You’ll Eat Well)
Taverna del Guerrino:
Set on the edge of the village with a view over the Chianti hills, this trattoria serves classic Tuscan dishes — think ribollita, tagliatelle al cinghiale (wild boar), and homemade desserts. Sit outside if the weather allows.
Local wine tastings:
Several small wineries are scattered just outside the walls. Some offer tastings by appointment — especially family-run spots producing Chianti Classico. Ask at the enoteca in Greve for recommendations.
Why Visit Montefioralle: It’s Quiet, Beautiful, and Exactly What You Came to Tuscany For
Because Montefioralle is what people imagine when they dream of Tuscany — but without the crowds. It’s quiet, close to Florence (about an hour), and feels untouched by time. Whether you come for a long lunch, a scenic walk, or just to breathe in the view, Montefioralle leaves a lasting impression.
It’s not flashy. It doesn’t try to impress. And that’s exactly why it does.
Barberino Val d’Elsa
If you’re road-tripping through the Tuscan hills between Florence and Siena, you could blink and miss Barberino Val d’Elsa — but please don’t. This tiny walled village is full of quiet charm, medieval character, and real Tuscan life. It’s not overrun with tourists, there’s not much in the way of souvenir shops — and that’s exactly why it’s worth a stop.
The old stone gate, the flowers in spring, the peaceful streets… it’s the kind of place that makes you slow down without even trying.
What to See and Do in Barberino Val d’Elsa (It’s Quiet — and That’s the Best Part):
- Porta Romana:This is the main gate into the village, and it’s often decorated with banners or flowers during local festivals. Walk through it, and you’ll feel like you’ve stepped back a few hundred years.
- Via Francesco da Barberino: This is the main street that cuts through the old town — and honestly, it’s more of a gentle stroll than a “street.” Stone houses, little balconies, and occasional views over the vineyards. Take your time and follow the curve to the opposite gate.
- Chiesa di San Bartolomeo: A small Romanesque church right in the center. Nothing grand, but full of heart — with traces of old frescoes and that quiet, sacred stillness you only get in old Italian churches.
- Viewpoints along the walls: There are spots where the old stone walls open up to reveal rolling Chianti hills and cypress trees stretching into the distance. Sunset here? Magical.
Best Time to Visit Barberino Val d’Elsa: Weather, Crowds, and Quiet Moments:
In May, the village often hosts Barberino in Fiore, a flower festival that transforms the streets into a sea of colors and potted plants. Local vendors set up stalls, there’s music, and the whole place feels alive and local — not staged.
But even if you miss the festival, the town is lovely year-round. Autumn brings golden light over the vineyards, and winter gives you the whole place almost to yourself.
Best Places to Eat and Drink in Barberino Val d’Elsa: Wine, Views, and Local Food:
- Osteria Il Campanellino: Right outside the historic walls. A simple trattoria serving comforting Tuscan dishes — homemade pasta, soups, grilled meats, and a great wine list.
- Casa Chianti Classico (in nearby Radda or Castellina): If you want to dive deeper into the world of Chianti wine, consider a short drive — this area is dotted with small wineries and tasting rooms. Barberino is a great base for exploring.
Castellina in Chianti
If you’re exploring the Chianti region and want a place that mixes medieval architecture, good wine, and a little bit of history — but without big crowds — Castellina in Chianti might be your perfect stop. It’s not a postcard village pretending to be old — it is old. With a fortress in the middle of town, Etruscan tombs just down the road, and wine shops everywhere you look, Castellina feels like the kind of place where time has taken its sweet time.
What to Do in Castellina in Chianti:
- Rocca di Castellina: Right in the heart of the village, this medieval fortress still stands tall — stone walls, tower, flag waving in the wind. You can walk through parts of it, visit the small archaeological museum inside, and if you climb the tower, you’ll get views across the vineyards and hills that stretch for miles.
- Via delle Volte: This is one of the town’s most unique features — an arched, tunnel-like street carved into the ancient walls, lined with openings that overlook the Chianti countryside. It’s cool, atmospheric, and feels a little secret. Great spot for photos, especially around golden hour.
- Historic center: Castellina’s core is compact and walkable — narrow stone streets, a few artisan shops, wine bars, and small piazzas. It’s not touristy, but it’s tidy and full of character. This is a good place to slow down and wander.
- Tumulus of Montecalvario: Just outside town, this ancient Etruscan burial mound is worth a quick visit. It’s a quiet, open-air site that reminds you Chianti’s history didn’t begin in the Middle Ages.
Best Places to Eat and Sip in Castellina in Chianti: Local Food and Great Wine:
- Ristorante Albergaccio di Castellina: Elegant but not stuffy. Classic Tuscan flavors done right — pici with ragù, perfectly cooked meats, fresh seasonal sides, and a long wine list featuring Chianti Classico producers from just up the road.
- Sotto Le Volte: A cozy, cave-like wine bar and bistro tucked under the fortress. Great for a glass of local wine, bruschetta, and light lunch.
- Enoteca Le Volte: Want to taste a few Chiantis before buying a bottle or two? This wine shop is friendly, knowledgeable, and happy to pour a sample and chat about the vineyards nearby.
Events & Local Life
- Festa del Vino (Summer): Castellina hosts wine events throughout the year, but in summer, the village really comes alive. Expect tastings in the streets, music, food stalls, and lots of toasting with Chianti Classico.
- Weekly Market (Saturday): A small local market with fresh produce, cheeses, and a few household goods. Nothing fancy — just real-life Chianti.
What Makes Castellina in Chianti Worth Visiting:
Because Castellina offers the best of Chianti without trying to be anything it’s not. It’s lived-in, welcoming, and beautiful in a quiet, effortless way. You can climb a medieval tower in the morning, sip wine at lunch, walk through ancient tombs in the afternoon, and watch the sunset from the town walls with a gelato in hand.
If that’s not the Tuscany you came for… what is?
San Donato in Poggio
There are places in Tuscany that feel untouched by time — not frozen, but gently living in the past. San Donato in Poggio is one of those places. Nestled in the Chianti hills, halfway between Florence and Siena, this small walled village doesn’t make a lot of noise. And yet, the moment you walk through its stone gate, it feels like something special.
No crowds. No rush. Just a few quiet streets, shuttered windows, and flowers in every corner. If you’re craving a break from the big-name towns, San Donato is exactly the kind of peaceful detour that stays with you.
Things to Do in San Donato in Poggio:
- Porta Fiorentina: This is the main entrance to the village — a medieval gateway that still watches over the calm stone streets inside. Start your walk here and let yourself slow down.
- Via del Giglio: The village’s main street is more of a gentle slope than a bustling road. It’s lined with stone houses, potted plants, old wooden doors, and the occasional cat napping in the sun. This is a place for strolling, not sightseeing.
- Chiesa di Santa Maria della Neve: A simple, peaceful church just off the main path. It’s not grand, but it’s honest — and often open to visitors looking for a moment of quiet.
- Piazza Malaspina: The main square, tiny and sun-soaked, is where locals still gather. You might find a few tables outside the wine bar, an open window with someone chatting from the kitchen, or the scent of lunch drifting from a trattoria nearby.
- Walls and Views: Walk along the village edge and you’ll find wide views of vineyards, olive groves, and rolling hills. At sunset, the light here turns golden and soft — pure Chianti magic.
San Donato in Poggio: Where to Eat Well and Enjoy a Glass with a View:
- La Toppa Trattoria: Family-run and friendly, this place serves up traditional Tuscan dishes like ribollita, grilled meats, and handmade pici. Nothing fancy — just really good food done the right way.
- Osteria del Campanellino (just outside the gate): If you’re staying nearby or passing through, this osteria offers a more refined take on local flavors. Great wine list, romantic outdoor seating, and views across the countryside.
- Bar I’Poggio: Need a coffee or aperitivo? This little bar by the square is a perfect local stop — relaxed, welcoming, and full of character.
Why Go to San Donato in Poggio? It’s Not Big, It’s Not Busy — and That’s the Point:
Because sometimes, the best parts of Tuscany aren’t in the guidebooks. San Donato in Poggio isn’t flashy, and that’s exactly its charm. You come here not to “see the sights” but to breathe, walk, and feel what slow living in Chianti is really like.
It’s perfect as a stop on a road trip, a base for exploring the wine region, or just a quiet afternoon away from the noise. And if you’re lucky, you’ll arrive when the bells ring through the valley and realize — this is exactly what you were looking for.
Province of Arezzo
Anghiari
Tuscany has its stars — the towns that everyone’s heard of, where buses line up and crowds spill into piazzas. And then there’s Anghiari. A quiet medieval village in eastern Tuscany, not far from the Umbrian border, that feels like a secret worth keeping.
It’s all stone — steep alleys, thick walls, and houses pressed tight together like they’re holding onto centuries of stories. You don’t come here to check off sights. You come here to walk, breathe, listen. Anghiari is slow travel in its purest form.
What to Do in Anghiari:
- Via della Liberta (and that iconic view): Before you even get into the village, stop for the view. There’s a sweeping curve in the road that shows off Anghiari clinging to its hill like a postcard brought to life. That’s the view from the famous Battle of Anghiari painting — the one Leonardo da Vinci started but never finished.
- Historic center: Wander uphill through flower-filled alleys and archways. It’s like a living museum, but without ropes or rules. Just stone, silence, and lived-in beauty. Follow the signs to Piazza Baldaccio, where locals still sit for coffee, and the rhythm of daily life hasn’t changed much in decades.
- Palazzo Pretorio & Museo della Battaglia: Right in the heart of town, this small museum tells the story of the 1440 Battle of Anghiari, a clash between Florence and Milan that helped shape Renaissance Italy. Leonardo was commissioned to paint it in Florence’s Palazzo Vecchio, but the fresco never survived. Still, the story remains — and here, it’s told well.
- Badia di San Bartolomeo: A quiet Romanesque church just outside the center. Step inside if the door’s open — you’ll find a cool, calm interior with faded frescoes and centuries of history.
Where to Eat in Anghiari: Just Good Food in a Quiet Town:
- Locanda al Castello: Set just near the old walls, this place feels like home. Traditional Tuscan dishes, excellent wines, and a view if you get the right table. Think pici, wild boar, and local olive oil that tastes like sunshine.
- Cantina del Granduca: Simple, rustic, and welcoming. Perfect for lunch after a long walk — great tagliere (meat and cheese boards), crostini, and house wine. Nothing fancy, but everything flavorful.
- Pasticceria Caffè de’ Medici: Grab a coffee or sweet pastry here. Locals still line up in the morning — always a good sign.
Events & Local Life in Anghiari:
- Palio della Vittoria (June): A local race that commemorates the Battle of Anghiari — but instead of horses, it’s all about barefoot runners charging uphill into the village. A mix of tradition, sweat, and community spirit.
- Mercatini d’Autunno (Fall Markets): Chestnuts, honey, local wine, and artisan crafts fill the village squares in late autumn. It’s a great time to visit — fewer tourists, crisp air, and plenty of seasonal treats.
Why Go?
Because Anghiari feels like it’s still holding something sacred.
Not in a grand, showy way — but in the little things. A door left ajar. A faded fresco. A quiet smile from a local passing by. It’s a place that rewards curiosity and slowness.
So if you’re heading to Tuscany and looking for something quieter, older, more real — this is it. Anghiari won’t ask anything of you. It just offers itself, and lets you fall in love at your own pace.
Cortona
Cortona is one of those towns that a lot of people have heard of — mostly because of Under the Tuscan Sun. And yes, it’s beautiful. But what makes it worth visiting isn’t the movie. It’s that the town still feels lived-in. It’s not overly polished. People still hang their laundry outside, the piazza is still full of locals, and there are corners where you can actually hear yourself think.
It’s up on a hill in the Valdichiana, and the views are what you’d expect: olive groves, vineyards, and rooftops that stretch into the distance.
But it’s the walk through town — the uneven stone streets, the worn-down steps, the smell of coffee and bread — that sticks with you.
Top Things to See in Cortona: From Etruscan Walls to Sunset Piazzas:
- Piazza della Repubblica: This is the main square and a good place to start. The Palazzo Comunale is the big building with the clock tower. You’ll probably pass through here a few times — for a coffee, a bench, a photo. It’s also where locals gather, especially in the evening.
- Via Nazionale: It’s Cortona’s only flat street. Everything else is uphill or downhill. You’ll find shops, wine bars, and a few restaurants here. It’s also a good shortcut through town.
- Church of Santa Margherita: Up above the town. If you’re up for a walk, it’s worth it — mostly for the view. The church itself is peaceful and has some local history behind it.
- Eremo Le Celle: About 2 km from town. It’s a Franciscan monastery built into the rock — very simple, very quiet. Not many tourists. If you’re looking for a break from towns and crowds, go here.
- MAEC Museum: If you’re into Etruscan or Roman history, this small museum is well done. It doesn’t take long to go through, and it’s right in the center.
Where to Eat in Cortona: A Few Honest Places:
- Trattoria Dardano: Classic, casual, and consistent. Always busy, so you might wait. Good pasta, house wine, and honest prices.
- La Bucaccia: Smaller, more curated menu — good if you want something a little more special but still local.
- Caffè Signorelli: Easy place to sit with a coffee or aperitivo and just watch people walk by.
Yes, This Is Where Under the Tuscan Sun Was Filmed
Yes, Under the Tuscan Sun was filmed here. Yes, you can go see the outside of Villa Bramasole (from the road — it’s private). But you don’t need to care about the movie to enjoy the town. It’s not overrun, and most people visiting aren’t here for that reason.
Should You Visit Cortona?
If you’re in the area — yes. Cortona is worth a visit. It’s easy to walk, has good food, and the views are excellent. You won’t need more than a day unless you want to use it as a base.
It feels real, and in a region where some towns can feel like museums, that’s not nothing.
Lucignano
Lucignano doesn’t show off. It’s not packed with must-see attractions or tour groups following umbrellas. And that’s exactly why it’s special.
This little hilltop town between Arezzo and Siena is shaped like a spiral — literally. The medieval streets wrap around themselves like a snail shell, which makes it oddly satisfying (and easy) to wander. You’re not really trying to get anywhere. You’re just walking through quiet alleys, flower pots on windowsills, and stone walls that haven’t changed in centuries.
Top Things to See in Lucignano:
- Museo Comunale & the Tree of Life: It’s a small museum, but worth the visit. The main reason? The Tree of Life — a gold reliquary from the 14th century, covered in coral and crystals. It’s strange and beautiful and completely unexpected in a place this small.
- Collegiata di San Michele Arcangelo: The main church at the top of town. Simple outside, but step in and look up — the ceiling is a surprise. You’ll probably have it all to yourself.
- The Town Walls: Lucignano is still fully enclosed by its medieval walls. You can follow bits of them and catch quiet views over the Val di Chiana, with barely a sound except birds and maybe a Vespa in the distance.
What to Eat in Lucignano: Simple Tuscan Food That Still Tastes Homemade:
- Il Goccino: A bit upscale, but still warm and friendly. Good wine list, dishes that change with the seasons. Sit outside if the weather’s good — the view is classic Tuscany.
- La Rocca: More rustic. Pici with ragu, grilled meats, local olive oil. Nothing fancy — just well done. And if you’re there during one of their food festivals (see below), eat whatever they’re serving. The locals know what they’re doing.
Lucignano’s Traditions Festivals:
- Maggiolata (May) A spring festival with flower-covered floats, folk costumes, and music in the piazza. It’s loud, colorful, and completely authentic — still run by the community, not a tourist event.
- Settimana Santa (Holy Week) Lucignano puts on a quiet, moving procession for Easter. If you’re in the area, it’s worth seeing how tradition still runs deep in small towns like this.
Province of Grosseto
Sorano
One of the “Tufa Towns” along with Pitigliano and Sovana, this Etruscan gem is built on a rocky outcrop and filled with twisting alleys and artisan shops. The Orsini Fortress now functions as a hotel.
Pitigliano
A breathtaking sight with houses that seem carved into the cliff. Known as the “Little Jerusalem” for its historic Jewish community (you can still visit the synagogue and try the local dessert, lo Sfratto). Visit during Settembre DiVino, when all the wine cellars open for tastings!
Sovana
An elegant one-street village with a peaceful vibe, flanked by a fortress and a cathedral. The local museum holds a mysterious treasure said to be tied to the Count of Monte Cristo.
Montemerano
Not far from the Cascate del Mulino hot springs, this jewel has a picture-perfect central piazza, tiny alleys bursting with flowers, and a curious painting called Madonna della Gattaiola—named for a hole once carved by a priest to let his cat into the pantry!