12 Enchanting Places in Tuscany That Look Straight Out of a Postcard

Every time I return to Tuscany, I get that same flutter of excitement driving through those rolling hills. The last time I visited, I found myself pulling over constantly just to stare at the perfectly aligned cypress trees and endless vineyards. Standing in front of Siena’s marble-striped cathedral at sunset, watching the facade glow golden, I realized why the beautiful places in Tuscany have captivated artists and dreamers for centuries.

From sipping Brunello in Montalcino’s medieval squares to watching the sun set behind Florence’s Duomo from Piazzale Michelangelo, each moment here feels almost surreal. After countless plates of pici pasta and way too many scoops of gelato, I’ve gathered my favorite spots across this incredible slice of Italy. Let me show you the places that keep drawing me back year after year.

Enchanting Places to Visit in Tuscany

Looking to explore Tuscany’s most beautiful places? From the rolling hills of Val d’Orcia to the historic streets of Florence, Tuscany is packed with stunning scenery. Stroll through the charming town of Siena, marvel at the art in Pisa, or explore the cultural richness of Lucca. Discover the serene allure of San Gimignano, the tranquil vineyards of Chianti, or the breathtaking views from Cortona. Whether you’re into history, art, or wine country, here are 12 of Tuscany’s most breathtaking spots!

1. The Old Town of Florence

• 📍 Location: Northern Tuscany, central Italy, along the Arno River
• 🏆 Best For: Art lovers 🎨, architecture enthusiasts 🏛️, history buffs 📜
• 📸 Top Experiences: Visiting the Uffizi Gallery, climbing Brunelleschi’s Dome, exploring Ponte Vecchio
• 📅 Best Time to Visit: April-May and September-October for pleasant weather and fewer crowds 🌤️
• 🏨 Where to Stay: Hotel Brunelleschi – Historic accommodation in the heart of the old town

The Old Town of Florence is the beating heart of Renaissance art and architecture, where every cobblestone street tells a story of artistic genius and cultural revolution. This UNESCO World Heritage site packs more masterpieces per square foot than perhaps anywhere else on earth, with treasures by Michelangelo, Botticelli, and Leonardo da Vinci around seemingly every corner.

The towering Duomo with Brunelleschi’s revolutionary dome dominates the skyline, while the nearby Uffizi Gallery houses one of the world’s most important art collections. Cross the medieval Ponte Vecchio bridge lined with jewelry shops, then escape the crowds in the peaceful Boboli Gardens. For the ultimate Florentine experience, climb to Piazzale Michelangelo at sunset for a panoramic view that captures why this city has inspired artists for centuries.

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2. The Old Town of Siena

• 📍 Location: Central Tuscany, about 1 hour south of Florence
• 🏆 Best For: Medieval history enthusiasts 🏰, photographers 📸, architecture lovers 🏛️
• 📸 Top Experiences: Exploring Piazza del Campo, visiting Siena Cathedral, watching the Palio horse race
• 📅 Best Time to Visit: May-June for pleasant weather, July and August for the famous Palio 🐎
• 🏨 Where to Stay: Palazzo Ravizza – Elegant historic hotel with garden views of the Tuscan countryside

Siena’s Old Town feels like stepping into a perfectly preserved medieval dream, with its warm terracotta buildings and winding lanes all converging on the spectacular shell-shaped Piazza del Campo. This UNESCO-protected center has remained largely unchanged since the 14th century, offering a more intimate and authentic Tuscan experience than its larger neighbor Florence.

The stunning black-and-white striped Siena Cathedral houses masterpieces by Donatello and Michelangelo, plus the extraordinary inlaid marble floor often covered for protection. Don’t miss climbing the Torre del Mangia for breathtaking views across the city’s 17 distinct neighborhoods, or “contrade,” each with their own fierce traditions and symbols. If you’re lucky enough to visit during early July or mid-August, you’ll witness the heart-stopping Palio horse race, when the piazza transforms into a racetrack for this centuries-old competition that drives the city into a frenzy.

3. San Gimignano

• 📍 Location: Central Tuscany, about 1 hour southwest of Florence
• 🏆 Best For: Photography enthusiasts 📸, wine lovers 🍷, medieval architecture fans 🏰
• 📸 Top Experiences: Climbing the Torre Grossa, walking the ancient walls, sampling award-winning Vernaccia wine
• 📅 Best Time to Visit: April-June and September-October for ideal weather and fewer crowds 🌤️
• 🏨 Where to Stay: Leon Bianco – Historic hotel overlooking the main piazza

San Gimignano rises dramatically from the Tuscan countryside, its 14 medieval towers creating one of Italy’s most unforgettable skylines. Known as the “Medieval Manhattan,” this remarkably preserved hilltop town once boasted 72 tower-houses built by wealthy families competing to display their power and prosperity.

Wander the narrow streets to discover hidden courtyards and artisan shops selling local ceramics and saffron, a historic specialty of the area. Climb the Torre Grossa, the tallest remaining tower, for spectacular 360-degree views of vineyards and cypress-lined roads stretching to the horizon. Before leaving, be sure to taste the crisp, distinctive Vernaccia di San Gimignano wine that’s been produced here since the 13th century and sample the world-champion gelato at Gelateria Dondoli in the main square.

4. The Leaning Tower of Pisa

• 📍 Location: Western Tuscany, about 1.5 hours west of Florence
• 🏆 Best For: Architecture buffs 🏛️, photographers 📸, bucket list travelers ✅
• 📸 Top Experiences: Taking perspective photos with the tower, climbing to the top, exploring Pisa Cathedral
• 📅 Best Time to Visit: April-May or September-October for comfortable temperatures and smaller crowds 🌤️
• 🏨 Where to Stay: Hotel Bologna – Comfortable lodging within walking distance of the Tower

The Leaning Tower of Pisa isn’t just a famous architectural mishap – it’s a remarkable example of medieval engineering innovation and adaptation. Standing 186 feet tall and tilting approximately 4 degrees, this iconic bell tower began leaning during construction in the 12th century due to unstable soil beneath its foundation.

While most visitors come for the obligatory “holding up the tower” photo, don’t miss exploring the entire Piazza dei Miracoli (Square of Miracles), a UNESCO World Heritage site that includes the magnificent Pisa Cathedral and the ornate circular Baptistery. For a unique perspective, purchase tickets in advance to climb the tower’s 294 steps for stunning views of Pisa and the surrounding landscape. The sloping floors inside create a disorienting experience that makes the climb unlike any other in Italy.

5. Val D’Orcia

• 📍 Location: Southern Tuscany, stretching south from Siena
• 🏆 Best For: Photographers 📸, wine enthusiasts 🍷, countryside lovers 🌾
• 📸 Top Experiences: Photographing cypress-lined roads, visiting hilltop towns like Pienza and Montalcino, wine tasting
• 📅 Best Time to Visit: May-June for green landscapes and wildflowers, September-October for harvest season 🍇
• 🏨 Where to Stay: Adler Thermae – Luxury spa resort utilizing the area’s natural thermal springs

Val d’Orcia embodies the Tuscany of dreams – rolling hills punctuated by cypress trees, golden wheat fields, and perfectly positioned farmhouses that seem arranged specifically to make photographers weep with joy. This UNESCO-protected cultural landscape has inspired artists for centuries and continues to define our collective image of the Tuscan countryside.

The region’s picturesque hilltop towns are destinations in themselves. Pienza, the “ideal Renaissance city,” offers perfectly preserved architecture and exceptional pecorino cheese, while Montalcino is home to the prestigious Brunello di Montalcino wine. Don’t miss the otherworldly landscapes of the Crete Senesi with its distinctive gray clay hills that create an almost lunar appearance. For the quintessential Val d’Orcia photo, head to the winding road near Podere Belvedere at sunrise when the early light creates a magical atmosphere of misty valleys and dramatic shadows.

6. Lucca

• 📍 Location: Northwestern Tuscany, about 1 hour west of Florence
• 🏆 Best For: Cyclists 🚲, history lovers 📜, music enthusiasts 🎵
• 📸 Top Experiences: Biking atop the Renaissance walls, climbing Torre Guinigi, attending Lucca Summer Festival
• 📅 Best Time to Visit: April-June and September-October for pleasant temperatures and outdoor activities 🌤️
• 🏨 Where to Stay: Palazzo Dipinto – Elegant boutique hotel within the walled city center

Lucca stands out among Tuscan cities for its completely intact Renaissance walls that now serve as an elevated 2.5-mile park perfect for cycling, jogging, or leisurely strolls. This charming city maintains its medieval street plan within these massive fortifications, creating an intimate atmosphere that feels worlds away from the tourist crowds elsewhere.

The city’s narrow lanes open onto lovely piazzas like the oval-shaped Piazza dell’Anfiteatro, built on the foundations of an ancient Roman amphitheater. For a unique perspective, climb the Torre Guinigi, with its rooftop oak trees offering shade and spectacular views. As the birthplace of composer Giacomo Puccini, Lucca celebrates its musical heritage with daily concerts in historic churches and the renowned Lucca Summer Festival that brings international acts to perform within the ancient walls. Don’t leave without trying the local specialty buccellato, a sweet bread flavored with raisins and anise.

7. Sorano, Sovana, and Pitigliano

• 📍 Location: Southern Tuscany, about 2 hours south of Florence and 1.5 hours northwest of Rome 
• 🏆 Best For: History enthusiasts 🏛️, photographers 📸, off-the-beaten-path explorers 🗺️ 
• 📸 Top Experiences: Exploring medieval streets, visiting Etruscan necropolises, wandering through ancient Jewish quarters 
• 📅 Best Time to Visit: April-June and September-October for pleasant temperatures and fewer tourists 🌞 
• 🏨 Where to Stay: Hotel della Fortezza – A transformed 11th-century fortress with panoramic views

Ever dreamed of stepping into a real-life fantasy village? These three medieval towns perched on volcanic cliffs will make your Instagram followers green with envy. Pitigliano, nicknamed “Little Jerusalem,” features a fascinating Jewish quarter with a restored synagogue and museum. The town emerges organically from the cliff, creating a dramatic skyline that glows golden at sunset.

Nearby Sorano offers winding streets filled with charming cafés and artisan workshops. I couldn’t believe the ancient engineering of the “Vie Cave,” mysterious sunken roads carved through the tufa by Etruscans. Don’t miss Sovana’s Etruscan necropolis with tombs dating back to the 3rd century BCE. The ambitious traveler can connect all three towns through an unforgettable hiking experience.

8. The Mountain Town of Cortona

• 📍 Location: Eastern Tuscany, perched on a hillside overlooking the Val di Chiana, about 1.5 hours southeast of Florence 
• 🏆 Best For: Art lovers 🎨, foodies 🍝, “Under the Tuscan Sun” fans 📚 📸 
• Top Experiences: Exploring Renaissance art at the Diocesan Museum, enjoying panoramic views from Fortezza del Girifalco, sampling local wines and cuisine 
• 📅 Best Time to Visit: May-June for lush countryside and the annual Archidado Joust festival 🏇 
• 🏨 Where to Stay: Villa Marsili – Elegant historic villa with stunning valley views

Want to live your own “Under the Tuscan Sun” moment? This perfectly preserved medieval town sits 600 meters above sea level with sweeping views that made me gasp the first time I saw them. Cortona manages to maintain its authentic charm despite its literary fame.

Art enthusiasts will love the Diocesan Museum, housing masterpieces by Fra Angelico and local son Luca Signorelli. The Etruscan Academy Museum contains fascinating artifacts, including a remarkable bronze chandelier from the 5th century BCE. Foodies should try the hearty pici pasta with wild boar ragù at family-run trattorias. Visit during the Archidado Joust in June when locals dress in medieval costumes and compete in a crossbow competition dating back centuries.

9. The Coastal Beauty of Viareggio

• 📍 Location: Northern Tuscan coast, about 30 minutes from Pisa and 1.5 hours from Florence 
• 🏆 Best For: Beach lovers 🏖️, architecture enthusiasts 🏢, carnival celebrators 🎭 
• 📸 Top Experiences: Strolling the Liberty-style promenade, attending the famous Carnival, lounging on wide sandy beaches 
• 📅 Best Time to Visit: Summer (June-August) for beach season, February for the vibrant Carnival celebrations 🎭 
• 🏨 Where to Stay: Grand Hotel Principe di Piemonte – Art Deco elegance facing the seafront

Need a beach break from museum-hopping? Viareggio offers a refreshingly different side of Tuscany with its stunning 3km-long promenade lined with pastel-colored Art Nouveau buildings. The vibrant atmosphere makes it perfect for travelers seeking both relaxation and culture.

The town’s spectacular Carnival celebration features enormous satirical papier-mâché floats that tower up to 20 meters high. Trust me, you’ve never seen political satire quite this creative or gigantic! Wide, well-maintained beaches provide perfect relaxation spots with organized beach clubs offering loungers and beachside dining. For active days, explore the nearby Apuan Alps for hiking or visit the aristocratic villas in Lucca, just 30 minutes away.

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10. Montepulciano

• 📍 Location: Southern Tuscany, about 2 hours south of Florence and 1 hour southeast of Siena 
• 🏆 Best For: Wine connoisseurs 🍷, medieval architecture fans 🏰, panorama seekers 🌄 
• 📸 Top Experiences: Wine tasting Vino Nobile, exploring Renaissance palaces, photographing Val d’Orcia views 
• 📅 Best Time to Visit: September-October for grape harvest season and perfect weather 🍇 
• 🏨 Where to Stay: Palazzo Carletti – Elegant rooms in a 15th-century palace in the historic center

Wine lovers, your Tuscan dream awaits in this Renaissance jewel perched dramatically on a limestone ridge. Montepulciano sits 605 meters above sea level with breathtaking views across rolling countryside toward Monte Amiata. The town produces the famous Vino Nobile di Montepulciano, consistently ranked among Italy’s finest reds.

Historic wine cellars extend deep into the tufa rock below elegant medieval palaces. The atmospheric underground aging rooms left me speechless during my first tour. Beyond wine, explore the main square, Piazza Grande, with its unfinished cathedral, and climb the imposing Palazzo Comunale for exceptional views. Visit the exquisite Church of San Biagio just outside the walls, or time your trip for the Bravio delle Botti festival, when districts compete in a barrel-rolling race through steep streets.

11. Volterra

• 📍 Location: Central Tuscany, about 1.5 hours southwest of Florence and 1 hour from Siena 
• 🏆 Best For: Archaeology buffs 🏺, alabaster craft lovers 🗿, vampire fiction fans 📚 📸 Top Experiences: Touring the Etruscan Museum, watching alabaster artisans at work, exploring the Roman theater 
• 📅 Best Time to Visit: April-June or September-October to avoid summer crowds and heat 🌞 
• 🏨 Where to Stay: Hotel La Locanda – Charming accommodation in a restored 16th-century palazzo

History buffs will fall hard for this time capsule town with perfectly preserved layers spanning three millennia. Volterra began as an important Etruscan center named Velathri before flourishing under Roman rule and again during medieval times. The excellent Guarnacci Etruscan Museum houses thousands of funeral urns and the hauntingly beautiful “Shadow of the Evening” bronze statuette.

What makes this town unique is its centuries-old alabaster crafting tradition. I spend hours watching skilled artisans transform the translucent stone into delicate sculptures in local workshops. Twilight fans might recognize Volterra as the fictional home of the Volturi vampire clan. Don’t miss the dramatic Balze clay cliffs slowly eroding at the town’s edge in a fascinating geological spectacle.

12. Chianti

• 📍 Location: Central Tuscany, stretching between Florence and Siena 
• 🏆 Best For: Wine enthusiasts 🍷, countryside lovers 🌄, slow travel advocates 🚲 
• 📸 Top Experiences: Wine tasting at historic estates, exploring hilltop villages, driving scenic cypress-lined roads 
• 📅 Best Time to Visit: May-June for green landscapes or September-October for harvest season 🍇 
• 🏨 Where to Stay: Castello di Spaltenna – Luxury accommodations in a converted 10th-century monastery

Want to live out every Tuscan wine country fantasy in one perfect trip? Chianti embodies everything thirty-somethings love about Tuscany. This picture-perfect region of rolling hills and ancient villages produces Italy’s most iconic wine, marked by the distinctive black rooster seal.

Explore by car or bicycle along cypress-lined roads connecting charming stone villages like Castellina, Radda, Gaiole, and Greve. Each town offers its own character and inevitable enoteca for wine tastings. The landscape unfolds as a patchwork of vineyards and olive groves dotted with stone farmhouses. Many historic estates welcome visitors, from intimate family operations to grand properties like Castello di Brolio, where modern Chianti wine was essentially invented. I recommend splurging on a dawn hot air balloon ride to witness the morning light transforming this quintessential landscape.

Frequently Asked Questions (FAQs) About Visiting the Beautiful Places in Tuscany

Are you looking for scenic city and cultural attractions? Or would you prefer a relaxing getaway in nature? Whatever you’re planning, Tuscany can accommodate your needs. Here are all the best spots in Tuscany you should know about.

Looking to expand your knowledge about the most scenic spots in Tuscany? Here are some common questions I get a lot about the best Tuscan attractions and activities.

What is the best time to visit Tuscany?

The best time to visit Tuscany is during the spring (April to June) and fall (September to October) when the weather is mild, and the countryside is in full bloom or displaying autumnal hues. These periods also see fewer tourists, making it ideal for exploring the region.

What is the prettiest area in Tuscany?

Tuscany, a region in central Italy, offers breathtaking landscapes, art, history, and culinary traditions. It brims with beautiful areas, and choosing the “prettiest” can be subjective. However, here are some standout areas with exceptional beauty:

1. Val d’Orcia: A UNESCO World Heritage Site, Val d’Orcia is one of the most beautiful areas in Tuscany. Its rolling hills, cypress-lined roads, medieval castles, and vineyards create a quintessential Tuscan landscape. Towns like Pienza and Montalcino add to the charm.
2. Chianti: Famous for its wine, the Chianti region offers stunning vineyard-covered hills, olive groves, and charming villages like Greve and Radda. It’s a perfect area for wine tasting and enjoying the rural Tuscan lifestyle.
3. Florence: The capital of Tuscany, Florence is a city of art and architecture. The view of the city from Piazzale Michelangelo, with the iconic Duomo and the Arno River, is breathtaking.
4. Siena: Known for its medieval streets and stunning cathedral, Siena’s historic center is a UNESCO World Heritage Site. The view from the Torre del Mangia over Piazza del Campo is particularly beautiful.
5. Lucca: Encircled by Renaissance walls, Lucca’s well-preserved historic center, charming streets, and beautiful churches make it a picturesque city to explore.
6. San Gimignano: Famous for its medieval towers, San Gimignano offers stunning views of the surrounding countryside. It’s often referred to as the “Manhattan of Tuscany.”

How many days do I need to explore Tuscany?

While you can get a glimpse of Tuscany in 3-4 days or in a week which allows you to explore the region. This includes some of its major towns, countryside, and vineyards.

Is Tuscany suitable for family vacations?

Absolutely! Tuscany offers a range of activities suitable for families, from exploring historic towns and castles to participating in cooking classes and enjoying beach days along the coast.

What is the most scenic part of Tuscany?

While Tuscany is filled with scenic landscapes, many consider the Val D’Orcia, with its rolling hills, cypress-lined roads, and medieval towns, to be the most picturesque part of the region.

Is Tuscany the most beautiful part of Italy?

Tuscany is undoubtedly one of the most beautiful regions in Italy, known for its picturesque landscapes, historic cities, world-class art, and culinary delights. Its rolling hills, vineyards, olive groves, and cypress-lined roads have become iconic symbols of Italian beauty.

However, Italy is a country rich in diverse landscapes and cultural heritage, and beauty is in many other regions as well. Here’s a glimpse of what some other regions have to offer:

1. Amalfi Coast: Located in the Campania region, the Amalfi Coast is famous for its stunning coastal cliffs, colorful villages, and crystal-clear waters.
2. Cinque Terre: In Liguria, Cinque Terre’s five cliffside villages overlooking the Mediterranean Sea are incredibly picturesque.
3. Venice: The Veneto region’s capital, Venice, with its canals, historic architecture, and unique charm, is a place like no other.
4. Lake Como: In Lombardy, Lake Como boasts dramatic scenery, elegant villas, and tranquil waters.
5. Sardinia: This island region offers beautiful beaches, rugged landscapes, and unique traditions.
6. Sicily: Rich in history and culture, Sicily boasts beautiful beaches, ancient ruins, and Mount Etna, Europe’s largest active volcano.
7. Dolomites: In the Trentino-Alto Adige region, the Dolomites offer breathtaking mountain landscapes, perfect for hiking and skiing.

What is the most famous part of Tuscany?

The most famous part of Tuscany is arguably the city of Florence, known for its Renaissance art, and architecture, and being the birthplace of the Italian Renaissance. However, areas like Chianti, known for its wine, and towns like Pisa and Siena also hold significant fame.

Are there guided tours available in Tuscany?

Yes, there are numerous guided tours available, ranging from city walking tours and museum visits to wine-tasting tours and countryside excursions. These tours offer insights into the region’s history, culture, and traditions.

Can I drive around Tuscany?

Driving is one of the best ways to explore Tuscany, especially its countryside. The region has well-maintained roads, and renting a car gives you the flexibility to visit off-the-beaten-path locations at your own pace.

Final Thoughts on Visiting Beautiful Places in Tuscany

Tuscany, with its rich tapestry of history, art, and nature, is a dream destination for many. From the architectural wonders of Florence to the serene landscapes of Val D’Orcia, every corner of this region beckons travelers with its unique charm. For those wondering where to go in Tuscany, the options are endless.

It does not matter if you are visiting Tuscany’s coastal towns, exploring its medieval villages, or simply soaking in the ambiance of its countryside, there’s something for everyone. The pretty places in Tuscany are not just limited to its popular destinations; even the lesser-known spots offer experiences that are both enriching and memorable.

As you plan your itinerary, remember that the true essence of Tuscany lies not just in the places you visit but in the moments you cherish. From its world-class wines to its timeless art, Tuscany is not just a region to explore; it’s a realm to experience. So, as you chart your journey through the places to visit in Tuscany, prepare to be enchanted by its beauty, culture, and soul.