Can we quickly agree that Italy’s old towns are pure magic – the kind that makes your Instagram followers double-tap before they can even process the beauty?

Just picture narrow medieval streets where time seems to have paused, the sunlight dancing on ancient stone walls, and charming corners that look like they’ve been pulled straight out of a postcard.

From the medieval towers of Bologna to the natural caves of Matera, you’ll quickly come to understand that these are not just historic locations but living works of art.

If you’re a digital nomad or a travel blogger, you’re in the right place because this blog will take you through Italy’s most Instagram-worthy, historic towns that are guaranteed to make your feed absolutely Bellissimo!

Top 10 Instagrammable Old Towns in Italy

1. Positano

Positano Old Town in Italy

Location: 1 hour from Naples

Positano, a jewel of the Amalfi Coast, is famous for its steep cliffs, pebble beachfront, and colourful houses which cascade down to the sea. The town, which was founded by the Greeks and later developed under the Romans, has a storied past as a maritime republic.

Things to Do in Positano Italy

  • Visit the Church of Santa Maria Assunta: The 13th-century church is renowned for housing the revered Byzantine icon of the Virgin Mary and its stunning dome which is made of majolica tiles.
  • Explore Spiaggia Grande: This is the main beach of Positano; it’s perfect for sunbathing and enjoying local seafood.
  • Hike the Path of the Gods: This scenic trail offers panoramic views of the coastline.
  • Shop for local crafts: Positano is famous for its handmade sandals and linen clothing.

What People Say About Positano on Tripadvisor?

As per reviews on Tripadvisor, Positano is a stunning yet challenging destination for Instagram lovers. Travellers advise taking a ferry early in the morning or late in the afternoon to dodge massive tourist groups. The town’s steep streets and endless stairs demand physical preparation, but the breathtaking views and colourful architecture make every step worthwhile for content creators seeking that perfect Mediterranean photograph.

2. Cortona

Cortona Old Town in Italy

Location: About 30 minutes from Arezzo

Cortona is a charming hilltop town in Tuscany with roots that date back to the Etruscan times. Its narrow streets are lined with medieval buildings and offer stunning views of the surrounding countryside.

Things to Do in Cortona Italy

  • Visit the Diocesan Museum: To see works by Renaissance artists and significant religious art from the region.
  • Explore Piazza della Repubblica: The town’s main square is perfect for watching other tourists and enjoying a coffee at one of its cafes.
  • Hike to Fortezza Medicea: The fortress offers breathtaking views over the Val di Chiana and is a great spot for photography.
  • Attend local festivals: Cortona hosts various cultural events throughout the year, including the Tuscan Sun Festival featuring music and art.

What People Say About Cortona on Tripadvisor?

According to Tripadvisor reviews, Cortona is a must-visit destination for visual storytellers. To get the best experience, travelers recommend being strategic about your visit – park in external lots, explore the town during less crowded periods, and expect to walk a lot.

The town’s elevated position offers stunning Tuscan landscape views, making it ideal for capturing picture-perfect Instagram content. The town’s diverse cuisines, cultural events, and historic architecture also make good, photogenic content for the gram.

Visitors suggest booking guided tours to get informed of the town’s rich history and go to destinations you won’t discover on your own.

3. Matera

Location: About 1 hour from Bari

Matera is famous for its ancient cave dwellings known as Sassi, which date back to prehistoric times. People have continuously inhabited this UNESCO World Heritage site for thousands of years, and in 2019, Matera was named the European Capital of Culture.

Things to Do in Matera Italy

  • Explore Sassi di Matera: To wander through these ancient cave dwellings, many of which are now homes, hotels, and restaurants.
  • Visit the Matera Cathedral: This stunning Romanesque cathedral offers panoramic views of the Sassi and features beautiful frescoes.
  • Tour Casa Grotta di Vico Solitario: This museum educates tourists on traditional cave living in Matera.
  • Experience local cuisine: Enjoy traditional dishes like cicoria (wild greens) and pane di Matera (Matera bread) in local restaurants.

What People Say About Matera on Tripadvisor?

Travellers on Tripadvisor highlight Matera as a picturesque Italian destination for Instagram-worthy travel as it’s a centuries-old city with extraordinary cave dwellings (Sassi) that climb dramatically up a mountain ridge.

Visitors praise its warm hospitality, rich history, and incredible architectural uniqueness. They say the best time to visit is in September or October because that’s when the weather is mild and there are fewer crowds.

The city’s transformation from a poverty-stricken area to a restored cultural treasure makes it an ideal location for extraordinary travel memories.

4. Volterra

Volterra Old Town in Italy

Location: About 1 hour from Pisa

Volterra is similar to Cortona as it’s also an ancient town with Etruscan origins, perched on a hilltop in Tuscany. Volterra is famous for its alabaster craftsmanship and well-preserved medieval architecture, which gives visitors a glimpse into Italy’s rich history.

Things to Do in Volterra Italy

  • Visit the Roman Theatre: This ancient site has hosted performances since the 1st century BC and continues to this day.
  • Explore Palazzo dei Priori: The oldest town hall in Tuscany features impressive architecture and offers guided tours.
  • Discover Etruscan ruins at Parco Archeologico: This archaeological park showcases remnants of Etruscan civilisation, including walls and tombs.
  • Taste local wines: Volterra is near several vineyards where you can enjoy wine tastings, including regional varieties like Chianti.

What People Say About Volterra on Tripadvisor?

Tripadvisor explorers praise Volterra as a photogenic alternative to crowded Tuscan destinations.

This medieval hilltop town parades a surreal architectural beauty with stone walls, narrow streets, and breathtaking landscapes that are perfect for social media. Photographers should arrive early or during the golden hour for the most dramatic shots. It also helps if you can get a guided tour by a local expert for context and unique perspectives.

Culinary enthusiasts will appreciate the exceptional local restaurants and traditional Tuscan cuisine.

5. Pitigliano

Pitigliano Old Town in Italy

Location: About 2 hours from Rome

Pitigliano, known as “Little Jerusalem,” is famous for its striking cliffside position and rich Jewish heritage. The town’s history dates back to Etruscan times, with many buildings carved from volcanic tuff stone.

Things to Do in Pitigliano Italy

  • Visit the Jewish Museum and Synagogue: Learn about Pitigliano’s Jewish community through exhibits detailing their history and culture.
  • Explore the Orsini Fortress: This medieval fortress offers stunning views of the surrounding landscape and insights into Pitigliano’s past.
  • Wander through ancient streets: The narrow alleys are filled with charming shops selling local crafts and delicacies.
  • Enjoy local cuisine at a trattoria: Sample traditional dishes made with fresh ingredients from nearby farms.

What People Say About Pitigliano on Tripadvisor?

According to Tripadvisor reviews, travel photographers will love Pitigliano as this extraordinary hill town offers breathtaking views, unique tuff stone architecture, and a rich cultural history.

The town’s Jewish quarter, Roman aqueduct, and Orsini Palace provide exceptional photographic opportunities. They say June is the best time to visit because you’ll get to capture the town’s wheat fields in its golden glory.

Travellers should use satellite navigation if they’re touring without a guide, explore neighbouring towns like Sorano, and plan around local siesta times.

6. Bologna

Bologna Old Town in Italy

Location: About 2 hours from Florence

Bologna is the largest preserved medieval city district in Italy, known for its towers, porticoes, rich culture, and great nightlife. With roots dating back over two millennia, it serves as a cultural hub with a rich academic history.

Things to Do in Bologna Italy

  • Climb Torre degli Asinelli: This iconic leaning tower offers breathtaking views after climbing its 498 steps.
  • Visit Piazza Maggiore: The heart of Bologna features stunning architecture, including Basilica di San Petronio.
  • Explore the Archiginnasio of Bologna: Once home to the University of Bologna, this historic building showcases beautiful frescoes and an anatomical theatre.
  • Taste Bolognese cuisine: Don’t miss trying tagliatelle al ragù (Bolognese sauce) in one of its many trattorias.

What People Say About Bologna on Tripadvisor?

According to Tripadvisor reviews, Bologna is an underrated Italian destination for visual storytellers and photographers. The city’s extraordinary 666-step portico pathway provides the perfect object for dramatic urban landscape shots, while local museums offer archaeological treasures that you can’t get tired of seeing.

They recommend locations such as Piazza San Domenico, historic covered walkways, and surrounding countryside for Instagram-worthy shots. Travellers should plan visits around August, explore local restaurants like Osteria Le Mura, and use convenient train connections to nearby cities.

7. Montagnana

Montagnana Old Town in Italy

Location: 1 hour from Padua

Montagnana is renowned for its well-preserved medieval walls and old town charm. Its history dates back to Roman times when it served as an important military outpost. Today, it’s celebrated for its beautiful architecture and tranquil atmosphere.

Things to Do in Montagnana Italy

  • Walk along city walls: The impressive fortifications offer scenic views and insight into Montagnana’s historical significance.
  • Visit Castello di San Zeno: Explore this medieval castle that played a crucial role in defending Montagnana during conflicts.
  • Discover Duomo di Montagnana: This cathedral features beautiful frescoes and intricate architectural details worth admiring.
  • Enjoy local prosciutto di Montagnana: Try this renowned cured ham at local delis or restaurants.

What People Say About Montagnana on Tripadvisor?

According to Tripadvisor reviews, Montagnana is an Instagram-worthy destination thanks to its medieval architecture and exceptional cuisine. The city’s historic walls and pizzerias like Pizzeria Palio are places you don’t want to miss out on as they’re the perfect photography locations.

The highlights of the town include wood-fired pizzas, local cured meats, and warm hospitality. Travellers should enjoy the town’s medieval atmosphere during dusk, affordable dining, and capture architectural details that transport visitors back in time.

8. Montepulciano

Location: 1 hour from Siena

Montepulciano is famous for its Vino Nobile wine production and Renaissance architecture. The hilltop town has been inhabited since Etruscan times and its charming streets are lined with wine cellars and art galleries that you can’t simply resist.

Things to Do in Montepulciano Italy

  • Wine tasting at local wineries: Experience Vino Nobile di Montepulciano at various vineyards offering tours and tastings.
  • Visit Piazza Grande: The town’s main square features impressive buildings like Palazzo Comunale and offers panoramic views of the town.
  • Explore Tempio di San Biagio: This Renaissance church outside town has stunning architecture and serene gardens.
  • Attend local festivals: Montepulciano hosts numerous events celebrating wine and local culture throughout the year.

What People Say About Montepulciano on Tripadvisor?

As per reviews on Tripadvisor, Montepulciano is a picturesque Tuscan town with stunning medieval architecture that makes it a dream destination for Instagram enthusiasts.

You can’t run out of photogenic locations because there are so many historic buildings and stunning scenery to choose from. However, some wellness centers in the area may not live up to expectations, so it’s advisable to research and choose reputable establishments carefully.

9. Civita di Bagnoregio

Civita di Bagnoregio Old Town in Italy

Location: 2 hours from Rome

Civita di Bagnoregio is often called “the dying town” because of its eroding cliffside location. The town was founded by Etruscans over two thousand years ago. It’s known for its stunning views and unique charm. Civita di Bagnoregio’s isolation from neighboring towns adds to its allure as a picturesque destination.

Things to Do in Civita di Bagnoregio Italy

  • Walk across the footbridge: The only access point offers breathtaking views as you approach this enchanting hilltop village.
  • Visit San Donato Church: Located in the main square, this church features beautiful frescoes that depict religious scenes.
  • Explore ancient ruins nearby: Discover remnants of Etruscan civilization scattered around Civita’s surroundings.
  • Enjoy local cuisine at quaint eateries: Sample traditional dishes made with fresh ingredients sourced from nearby farms.

What People Say About Civita di Bagnoregio on Tripadvisor?

As noted by Travellers on Tripadvisor, Civita di Bagnoregio offers a captivating blend of history and natural beauty. However, the challenging terrain, particularly the bridge and steep paths, can be daunting for some visitors, especially those with mobility issues.

Travellers advise that you plan accordingly, consider alternative transportation options, and check the weather conditions, as fog can dampen the tourism experience.

10. Orvieto

Location: 1.5 hours from Rome

Known for its stunning cathedral adorned with intricate mosaics, Orvieto sits on a volcanic rock cliff in Umbria. Its history dates back to Etruscan times when it served as an important cultural centre.

Things to Do in Orvieto Italy

  • Visit Orvieto Cathedral (Duomo): Admire its stunning facade decorated with colourful mosaics depicting biblical scenes.
  • Explore underground tunnels (Orvieto Underground): Discover ancient caves used for various purposes throughout history.
  • Taste local wines at Enoteca Regionale del Lazio: Sample Orvieto Classico wine produced at local wine shops or bars.
  • Stroll through Piazza del Duomo: Take a walk in this picturesque square and make a detour at any of the cafes surrounding the place.

What People Say About Orvieto on Tripadvisor?

As per reviews on Tripadvisor, Orvieto is a captivating hilltop town in Italy that offers a serene escape from bustling cities. Travellers suggest exploring its charming streets, admiring the magnificent Duomo, and indulging in local cuisine at cozy restaurants.

The town’s unique atmosphere and stunning views make it a must-visit holiday destination for history and culture enthusiasts.

Frequently Asked Questions - FAQs

What is the oldest town in Italy?

Matera is widely considered as the oldest continuously inhabited city in Italy. Its Sassi district, a network of cave dwellings carved into the rock, dates back to the Paleolithic era. This ancient city is like a portal into human history, with several layers of civilization visible in its architecture and archaeological finds.

Are there UNESCO World Heritage Sites within Italy's ancient towns?

Yes, many Italian old towns are UNESCO World Heritage Sites. Notable examples include the historic centers of Florence, Venice, and Siena, each showcasing exceptional architecture and cultural heritage that reflect Italy’s art and history.

What distinctive crafts or souvenirs can be found in Italy's historic towns?

In Florence, visitors can find exquisite leather goods and handmade jewelry. Bologna is famous for its traditional balsamic vinegar, while the Amalfi Coast is known for its vibrant ceramics and limoncello, perfect for bringing a piece of Italy home.

What medieval towns are near Rome?

There are several – Orvieto, Pienza, Spoleto, and Todi, all of which offer a glimpse into Italy’s rich history and cultural heritage, making them ideal destinations for history buffs and travellers seeking authentic experiences.

Which ancient towns in Italy are known for their distinctive architecture?

Cities such as Venice, with its Byzantine and Gothic influences, and Siena, celebrated for its medieval buildings and Gothic architecture, are examples of Italian towns where architectural heritage is a focal point for visitors.

Conclusion

Italy’s old towns offer a captivating blend of history, architecture, and stunning landscapes, making them perfect destinations for photography enthusiasts and travelers alike. From the cliffside charm of Positano to the ancient allure of Matera, each town tells its own unique story through its streets, landmarks, and local culture.

Whether you’re enjoying local cuisine in Bologna or exploring the Etruscan ruins in Volterra, these towns provide an authentic glimpse into Italy’s rich heritage. Visiting these Instagrammable locations not only enriches your travel experience but also allows you to capture the timeless beauty that defines Italy’s enchanting landscape.