Italy is a country that continues to capture the hearts of millions of visitors each year, with it’s world-famous cuisine, rolling green hills, breathtaking coastline and culture-rich cities. It is the smaller, lesser known towns and villages, however, that I find really capture the beauty and uniqueness of this gorgeous nation. Here are my recommendations, combined with a handful of professional travel writers, of which most charming cities, colourful villages and small towns in Italy you simply have to visit!
Feature Image Credit: Cinque Terre by Christine from Christine Abroad
Most Beautiful Small Towns in Italy
24. San Marino Old Town, San Marino
Technically San Marino is it’s own country with it’s own government (and TWO Presidents!) but as it’s totally encircled by Italy and most people won’t visit one without visiting the other, I’ve decided to give it pride of place on this list. The fact that it’s also one of the prettiest and most historic small towns in the world helped my decision!!
San Marino is said to be the oldest Sovereign State and Republic in the world, founded way back in 301 A.D. It’s historic (but tiny) old town sits atop Mount Titano with a unparalleled 365 degree view of the San Marino and Italian countryside below it. Spend a few hours visiting San Marino’s famous three towers and the beautiful cobbled streets of the old town, then watch the sunset from one of the smallest nations on earth.
Where to stay: I stayed in Hotel Titano, a small property in the old town with gorgeous sunset views from their outdoor restaurant terrace. The window in my room opened right up onto a quiet piazza – which made me feel like I was waking up to an endless dream state!
23. Burano, Venice
Suggested by Josie from JosieWonders
Where to stay: If you want to stay the night in one of most picturesque places in the world, we recommend checking in to the lovely CasaBurano, where prices start from just €126 per night if you book direct. Also, their website offers up some fascinating stories about the locals that live here!
Small towns on the Amalfi Coast
22. Positano, Amalfi Coast
Suggested by Silke from Happiness and Things
With its pastel-coloured houses that appear to be stacked on top of each other like colourful dice, Positano must be one of the most picturesque places to see in Italy. You will find this old fishing village on the famous Amalfi Coast, where sheer limestone cliffs meet the sea. As a result of this seemingly forbidding coastal landscape, visitors to the area are greeted with amazing views of the blue Mediterranean Sea. Positano is a great stop on an Amalfi Coast road trip as well as an excellent shore excursion destination from nearby Naples. Is Naples worth visiting? Find out more.
Many people who visit Positano will arrive by ferry to explore the narrow stepped roads and browse the dozens of shops and stylish boutiques. Others will travel the coastal route with its many tunnels, turns and hairpin bends. Be it as it may, Positano, the backdrop of countless Italian movies from the 1960’s, remains one of the most intriguing towns to visit in Italy. Of all the small towns in Italy, this might be the most famous!
21. Sorrento, Amalfi Coast
Recommended by Stephanie from History Fan Girl
20. Ravello, Amalfi Coast
Suggested by Andra from Our World To Wander
When you talk about Italy’s Amalfi Coast, everybody will think about the famous Positano or Amalfi towns. But somehow, the quaint and charming little town of Ravello is overlooked. What makes this one special is the fact that it is situated above Amalfi, in the hills, overlooking the coast. Its location thus provides a jaw-dropping view over the Mediterranean Sea.
The best way to explore this magical little town is by merely wandering around, get lost around its narrow cobbled streets. Start from the main square, marked by an Italian-style cathedral and try not to get absorbed by the mesmerizing ceramics shops. And make sure to stop at Villa Cimbrone, a hotel but also a public garden with superb viewpoints. You can easily spend a couple of hours in its enchanting garden, escaping the summer heat. So simply taste the magic of Amalfi Coast from the quiet town of Ravello.
Small towns in Lombardy
19. Mantua, Lombardy
Suggested by Nam from Laugh Travel Eat
A Unique Activity? Why not try your hand at an Italian cooking class at Amy’s Cuchina on Lake Como? You can spend a morning in Amy’s apartment learning to cook your favourite Italian Cuisine…then go home and cook for all your friends!
18. Bellagio, Lombardy
Suggested by Ryazan from Everything Zany
Situated at the Lake District of Northern Italy, Bellagio captures the heart of many with its natural charm and stunning landscape of the alps and Lake Como and Lecco.
Bellagio is one of the best places to visit in Italy and the main highlight of Northern Italy. The green backdrop of the Italian mountains gives a unruffled view of the town with brightly yellowish town house dotted around the foot of the mountain range.
Due to Bellagio’s picturesque landscape and fairy tale charm lots of Hollywood films used this town as their filming location like Star Wars and Oceans 11 to name a few.
Bellagio has also been a favourite holiday destination for the rich and famous as well as the royals of Europe throughout the decades. On our visit to Bellagio, we stayed in the historical and glamorous Grand Hotel Villa Serbelloni, which has been one of the integral part of this fairytale like town with its grandeur and social impact in Bellagio’s history.
17. Cagnò, Trentino
Suggested by Allison from Eternal Arrival
Cagno is a small village in Italy’s Val di Non and it is one of the prettiest small villages in all of Italy. What makes Cagno so special is that it has gorgeous views over the rest of the valley, which is full of apple orchards and vineyards, looking into the gorgeous blue Lago di San Giustina below.
From Cagno, you can get a great view at the Hotel Viridis, which also has an excellent restaurant and makes its own gelato. The village itself is very small and quiet, but it’s a great base to do other things in Val di Non like kayak on the lake, explore the canyons of Rio Novella, explore the nearby castles, or eat lunch at a delicious agroturismo, a restaurant where all the food is locally sourced and cooked using traditional methods.
Beautiful towns of the Cinque Terre
16. Corniglia, Cinque Terre
Suggested by Sonja from Migrating Miss
Want to do a Cinque Terre tour? Here’s a review of the best one from Florence…
15. Riomaggiore, Cinque Terre
Suggested by Christine from Christine Abroad
The picturesque village Riomaggiore is one of the most beautiful and one of my favorite villages of Cinque Terre with its colorful houses, cozy environment, and view of the Mediterranean Sea. Riomaggiore is located in a small valley surrounded by the blue sea, cliffs, and lush vines. It’s dating back to the 13th century and is known for its wine that’s produced right next to town.
What makes Riomaggiore so special is the fact that it’s kind of bigger than the other towns, but still not too pricey. There’s a healthy mix of budget travel and higher standard restaurants and hotels. From here it’s also easy to go to La Spezia, which is a bigger city compared to the Cinque Terre villages.
In Riomaggiore, you can also, of course, enjoy the traditional snack/food – fresh calamari and fish in a cone with fries and sauce. It comes in various sizes and is equally popular among locals and tourists. It is also from Riomaggiore that you can walk the famous “walk of love”.
14. Vernazza, Cinque Terre
Suggested by Alex from Swedish Nomad
Vernazza is one of the most colourful and picturesque villages of Cinque Terre. It’s one of my favorite villages in all of Italy, and might be one of the best places I’ve photographed as well. But not only is it beautiful, Vernazza is also lively with shops and restaurants.
To get the best view, you walk up to the walking trail towards Monterosso, and just at the beginning of the trail, you’ll be met by the iconic view over Vernazza from above. There’s also another one from the opposite side of the town when you walk from Corniglia, that’s perfect for sunset photos.
Some of the best things to do here is simply to buy an ice cream and stroll around, go down to the small marina, and afterwards go for a pizza and some aperol spritz. To get to Vernazza, you can either walk from Monterosso al Mare or Corniglia, or take the Cinque Terre shuttle train or minibus.
Small Beach towns in Italy
12. Cefalù, Sicily
Suggested by Steph from The Mediterranean Traveller
If there’s one thing better than a picturesque Italian town, it’s a picturesque Italian town by the beach! The beautiful Sicilian coastal resort Cefalù has it all; culture, charm, cobbled streets, and great scenery. It even has a UNESCO World Heritage-listed cathedral, where the star attraction is its well-preserved Byzantine mosaics.
The narrow medieval alleyways are lined with cute shops, seafood trattorias and wine bars. Cefalù is small and easily walkable, and the short train journey from Sicily’s capital city of Palermo makes it a popular with Italian holidaymakers who rate its combo of history and golden beach. And rightly so – it’s is one of those places I just didn’t want to leave. The view of the town’s unique waterfront whilst swimming in the sea is stunning and the chocolate hazelnut gelato is out of this world (in fact it’s reason in itself to visit).
11. Ragusa, Sicily
Suggested by Leanne from The Globetrotter GP
Sicily is full of fairytale towns but Ragusa is one of my favourites. One of the several Baroque cities in the South East part of the Italian island, this city is brimming with charm and character. If you’re a fan of cobbled alleys, old churches and Italian ice cream then Ragusa will be a perfect stop on your Sicily itinerary.
10. Capri Island
Suggested by Nicole from Travelgal Nicole
Capri is an idyllic island in the Mediterranean Sea about an hour boat ride from Naples. Anacapri is the second of two towns on the island of Capri and is located on the slopes of Mount Solaro. Its about a 10 minute bus ride from the main town of Capri so it is easy enough to stay in Anacapri. It is a quiet picturesque town with quiet lanes, wild landscapes and rocky cliffs.
Anacapri is a concentration of Mediterranean colours, scents, and sounds. It’s the place you go if you don’t love crowds and want to experience the more authentic side of the island.
The hotels are also much cheaper in Anacapri but you are still close to all the main attractions such as Mount Solaro and the Blue Grotto. The Blue Grotto is a sea cave that is only accessible by wooden rowboat. Once inside the cave opens up and you can see the light reflecting off of the water.
Hill towns in Italy To Visit
9. Ostuni, Puglia
Suggested by Nadine from Le Long Weekend
La Città Bianca (the white city), as it’s known to the locals, is a hilltop village in the beautifully rugged region of Puglia. It sits perched above a landscape of ancient olive trees that stretches out as far as the Adriatic Sea.
The old town looks just as good from afar as it does once you venture in. Winding white alleyways and wonderfully ramshackle streets lead you to delightful scenes and offer views over the bucolic landscape below. Its charm is achingly similar to that which you’d find on a Greek Island. But that’s not by coincidence! Ostuni was completely rebuilt by the Greeks after it was destroyed in the Punic Wars. Indeed, even the name Ostuni comes from the Greek Astu néon, – which translates to ‘new town’.
Be sure to catch the bustling and colourful Saturday markets, and seek out one of the many amazing family-run restaurants tucked behind the thick whitewashed walls. For more Puglia Inspo, check out thus Puglia road trip itinerary.
8. Matera, Southern Italy
Suggested by Shandos from TravelNuity
Matera is an Italian town that looks like it belongs from a distant period in the past, which is true in many ways. It’s hillside is covered with houses carved into the rock, cave dwellings where people have lived for centuries, all the way back to the Bronze Age. Shortly after WWII an outcry went up over Italy when attention turned to the conditions of the people still living in these caves, without sanitation or electricity. In the following decades most of the residents were moved most out into newer apartment buildings, which now form the centre of the town, the caves left to decay. But these days many hold B&Bs and small restaurants, although modernity has largely left the caves untouched.
There’s not even any small supermarkets or pharmacies, let along multi-national outlets. For this reason you may recognise Matera from movies such as the Passion of Christ, where the streets and houses stood in for Jerusalem of 2000 years ago. But this is definitely in Italy, and a fairytale destination for visitors of today.
7. Nova Levante, Northern Italy
Suggested by Mike of 197TravelStamps.com
The mountainous north is one of the best regions to experience the diversity of Italy. The region of South Tyrol is a predominantly German speaking part of Italy. The area is most famously known for the impressive mountain ranges of the Dolomites. Nova Levante, or Welschnofen in German, is a small fairytale town surrounded by the incredible mountain ranges of the Rosengarten and the Latemar Mountain, which are part of the UNESCO World Nature Heritage.
If you are looking to get away from the stress and fast pace of the big cities, this is just the place to go. During the summer months, the Dolomites are the ideal spots for hiking and during the winter months, you can race down the slopes with your skies.
Thanks to the amazing fusion of Austro-Tyrolean and Italian culture and cuisine, you can find some incredible Austro-Italian dishes. But, if you feel like you need pizza and pasta during your time in Italy, you won’t be disappointed either.
6. Montepulciano, Tuscany
Suggested by Dhara from Not About The Miles
If you are touring Tuscany, the picturesque Renaissance town of Montepulciano, about 40 miles south of Siena, is a must visit. One of the best small towns in Tuscany, this gorgeous town is set high on a ridge overlooking the Val d’Orcia and the Val di Chiana, and you get stunning views of the surrounding countryside from here.
Where to stay: Why not stay at Follonico, a unique country house set in the rolling hills of Tuscany close to Montepulciano? It’s owned by a local family a set amidst organic gardens, vineyards and farmland. This is the places to stay for a true rustic feel with a warm Italian welcome.
5. Siena, Tuscany
Suggested by Emily from Kids and Compass
Siena is one of the most beautiful hilltop towns in Tuscany. Built uniformly of red brick, it’s a lovely example of medieval Italian architecture and a must-see if you’re in the region. The centre of the town is pedestrianised and one of the best things to do is simply to get lost in the narrow streets and soak up the atmosphere. Spot the sigils of the districts of Siena as you walk; they’re displayed on flags.
Siena is most famous for its central piazza; Piazza del Campo. This semi-circular piazza is used as a setting for a horse race, held between the different districts of Siena twice every summer. Even if you don’t manage to catch the horse race, you can’t help but be drawn to the Piazza. A highlight (pun intended) is to climb the Torre del Mangia, the tower which dominates the Piazza. The view from the top over the red-bricked city and the Tuscan countryside beyond is spectacular.
After you’ve explored the Piazza, head through the twisting streets towards the dark green and white marble cathedral. Inside you’ll find sumptuous artwork including sculptures by Michaelangelo and the library in particular shouldn’t be missed.
Unique activity? Want to do something special while in Tuscany? Local website Tuscany Now and More offers a range of fun activities in the region from Hot Air Ballon rides to Truffle Hunting! Sounds like my type of holiday!
Must Visit Towns and Cities in Emilia Romagna
4. Parma, Emila Romagna
The town of Parma is famous, first and foremost, for one very important thing: being the home of true parmigiano-reggiano cheese, a substance that I think we can all agree the world would be a worse place without.
If you’ve ever hoped to tour a parmigiano-reggiano factory and marvel at the sight of hundreds of wheels of aging cheese yourself (just me?), this is definitely the place for you–but it’s also not the only reason to come
Delightfully colorful Parma is an easy day trip from nearby and better-known Bologna, and in addition to being home to some truly world-class cuisine, it also boasts adorable streets that are perfect for getting lost in, an impressive 17th century theatre built entirely from wood, beautiful cafes, and some of the most exquisite cathedral interiors
we have seen in Italy (don’t miss the Parma Cathedral while you’re there!). Looking for places to stay in Bologna? Why not try out Airbnb.
3. Brisisghella, Emila Romagna
Of all the beautiful cities and small towns in Italy I have visited, Brisighella remains my favourite. I still can’t work out exactly why I love it here so much, but i’m guessing it’s a combination of factors. First of all, it’s less than an hour from Bologna, the city of food (Gods!), so very easy to reach on a day trip. Next of all, there are virtually no tourists around which makes it a dream to visit. There are three hills overlooking the town, each with an important historical monument; a fortress, a clock tower and a church. The walk from one to the next is breathtaking, with panoramic views of the red and orange roofs of the village, passing by vineywards, green fields and looking down on impossibly windy roads!
Famous for its olive oil, there’s a small cooperative in the village to buy local products and the gelateria on the town square has some of my best gelato I tasted in Emilia Romagna!
2. Bologna, Emilia Romagna
Suggested by Bilyana from Owlovertheworld
1. Ferrara, Emilia Romagna
Suggested by Patrick from German Backpacker
The university town Ferrara in Italy’s Emilia-Romagna region is not as touristic as nearby Milan or Venice, but certainly worth a visit. The town is easily reachable as a day trip from Bologna and captivates with its historic city centre, which you can explore by foot or by bicycle. Make sure to visit the beautiful castle in the heart of Ferrara and climb on top of the tower for a wonderful view of the town. You won’t find big tour groups and overcrowded sights in Ferrara; therefore, you can fully enjoy the atmosphere in this fairy-tale town.
Ferrara is especially popular for students thanks to its big university campus. While wandering through the narrow cobblestone streets, you’ll find amazing picture opportunities and especially in the evening, the town centre comes alive with its cafés, restaurants and bars. Sit down on the main square after some sightseeing and enjoy a delicious gelato or an Aperitivo while watching the locals and their dolce vita. Ferrara is still a hidden gem – but you’ll certainly enjoy your stay!
Do you think there are some fairytale towns in Italy that we’ve forgotten about? Please leave a comment with your suggestion and if you enjoyed reading this post, please consider PINNING IT for later.
Last updated on September 12th, 2023 at 04:32 pm