Italy’s Hidden Gems: 10 Enchanting Small Towns You Can’t Miss

From cliffside villages along the Amalfi Coast to colorful fishing islands in the Venetian Lagoon, Italy is filled with charming and picturesque small towns. As an Italy expert and avid traveler, I’ve explored many hidden gems across the country that offer stunning scenery, old-world architecture, mouthwatering cuisine, and that iconic dolce vita lifestyle.

Though large, famous cities like Rome, Venice, and Florence rightfully top many travelers’ Italy bucket lists, some of the country’s most beautiful and photogenic destinations are its lesser-known small towns that feel frozen in time. Take it from me – don’t just stick to the major tourist hubs! You absolutely must get out and explore some of these postcard-perfect Italian towns.

Positano: One of Italy’s Most Photographed Cliffside Villages

Perched dramatically on Italy’s gorgeous Amalfi Coast with pastel-colored clifftop homes overlooking the deep blue Mediterranean waters below, Positano is arguably one of the country’s most beautiful small towns. This vertical village cascades down towards beaches, tiny piazzas, and a lovely historic town center filled with high-end shops, galleries, and restaurants serving seafood caught fresh daily.

I’ll never forget sitting at an outdoor cafe, enjoying wine and the infectious energy of this luxury resort town where the dolce vita lifestyle was on full display. From families passing by on their way to the beach to an evening passeggiata under strings of lights with laughing couples and friends, Positano exudes both relaxation and romance.

Top Things to Do in Positano

• Take photos of the iconic mountains-meet-sea views, especially from the Spiaggia Grande beach looking back at the village.
• Go shopping for art, ceramics, linen dresses, and sandals along the stylish boutique-lined streets.
• Rent a boat and explore hidden grottoes and bays only accessible from the sea.
• Wander through narrow alleyways draped in brilliant bougainvillea flowers.
• Relax at an outdoor cafe and do as the locals do – enjoy an Aperol spritz cocktail paired with seafood as you watch the world go by.

Cinque Terre: Italy’s Fairytale Cliffside Villages

I’ve traveled all over Italy, but nowhere rivals the raw, natural beauty of the Cinque Terre region, with its string of centuries-old seaside villages dramatically perched on the rugged cliffs of the Italian Riviera. A UNESCO World Heritage Site, Cinque Terre’s isolation and difficult-to-access terrain left these fishing villages suspended in time, unspoiled by modern overdevelopment even today.

As I took the cliffside trails and trains connecting Riomaggiore, Manarola, Corniglia, Vernazza and Monterosso, each pastel village seemed even more picturesque than the next. With brightly painted houses, vineyards, charm to spare and spectacular vistas of the Ligurian coastline everywhere, Cinque Terre tops many travelers’ lists of the most beautiful place they’ve ever seen, mine included!

Don’t Miss in Cinque Terre

• Hiking the gorgeous coastal trails between villages for jaw-dropping vistas (wear good shoes!).
• Sampling regional specialties like pesto, anchovies, freshly caught seafood and Sciacchetrà wine.
• Exploring charming vine-covered alleyways and stepping inside little cliffside churches.
• Hunting for souvenirs in local shops, like ceramics painted with vibrant edgy designs.
• Watching local fishermen sailing colorful boats into tiny harbors with the day’s catch.

I’ve only scratched the surface of what makes Italy home to some of the world’s most beautiful small towns! Beyond Positano and Cinque Terre, places like Taormina, Procida, San Gimignano, Portofino, and more await to charm you with their scenery, history, cuisine, and that picturesque Italian lifestyle.

Taormina, Sicily: Breathtaking Views of Mt. Etna & the Sea

The gorgeous cliffside town of Taormina on the Italian island of Sicily has long been a favorite hilltop retreat of writers, artists, and wanderers from all over the world. With ancient ruins, medieval structures, sweeping seaside views of Mt. Etna, and no shortage of charm, it’s easy to see why Taormina seduces every visitor who comes to Sicily’s shores.

Beyond the postcard-perfect scenery and lively energy, I loved exploring Taormina’s winding historic streets lined with lively cafes and shops selling everything from ceramics made by local artisans to sweet Sicilian treats like cannoli.

Top Sights in Taormina

• The incredibly preserved Greek theater for stunning panoramic views combined with a trip back in time.
• Via Veneto, the pretty pedestrian thoroughfare filled with high-end boutiques, galleries, and jewelry stores featuring the Coral Roses that Taormina is famous for.
• Isola Bella, a tiny island with picturesque coves and nature trails just below the town, accessible via cable car.
• Castelmola, an adjacent mountaintop village overlooking Taormina and offering some of Sicily’s best views of vineyards and Mt. Etna.

Procida – An Island of Unrivaled Beauty Off Naples

Venturing just off the coast of frenzied Naples, I uncovered Procida, whose mostly untouched pastel-hued fishing villages offer a delightful tranquility. With its calendar-worthy marina stuffed with typical Italian fishing boats, compelling historic churches, and irresistible sleepy, Mediterranean vibe, it came as no surprise to learn Procida has been used as a charming backdrop for numerous Italian films.

Beyond Procida’s technicolor fisherman’s houses seemingly custom built for tourists’ cameras, I found so much joy immersing myself into humble daily island life – savoring just-caught seafood by the waterside as the sun set behind pastel facades.

Top Procida Experiences

• Discovering hidden Caribbean-like coves and beaches that rival Capri’s beauty, especially Spiaggia dei Tuzzoli.
• Exploring backstreets hardly wider than a single person in the Corricella district’s rainbow of houses.
• Sampling sweet delicate lemon liqueurs made from the island’s famous homegrown lemons.

Here is the remainder of the blog post on Italy’s prettiest small towns:

San Gimignano: Medieval Tuscan Hill Town

Rising out of the Tuscan countryside, the postcard-perfect medieval town of San Gimignano transports visitors back in time with its iconic stone towers kissed by golden hour light. Beyond the many towers giving San Gimignano its nickname as “Medieval Manhattan,” inside the 13th-century walls I discovered an intimate sanctuary filled with Romanesque architecture, vibrant local wine, and irresistible Italian small town life.

What to See and Do

• Climb the tallest tower, Torre Grossa, for sweeping views of vineyard-dotted hills peppered with cypress trees
• Explore Piazza Duomo, the enchanting heart of town framed by the stone towers and historic palazzos
• Sample award-winning wines like Vernaccia di San Gimignano at local cantinas
• Shop for saffron and olive oil produced in the Tuscan hills
• Make day trips to Florence, Siena and the Chianti wine region

Portofino: Where the Rich & Famous Retreat

The colorful harbor village of Portofino has attracted Italian high society, A-list celebrities and visitors. Escaping for a bit of glamour on the Italian Riviera’s most charmingly picturesque stretch of coastline. Beyond paparazzi keeping an eye out for famous faces docking their yachts. I found Portofino has history and beauty rounding out its offerings.

Nestled in the cliffs around a sheltered bay dotted with fishing boats, multicolored resort hotels, and al fresco restaurants lining the harbor, Portofino embodies the appealing, easygoing rhythm that initially seduced the Italian jet set. Life here seems dedicated wholly to la dolce vita.

What Not to Miss

• Exploring the historical Castello Brown fortress for breathtaking views over the town’s terracotta rooftops to the sea
• Browsing exclusive designer boutiques selling Chanel and Gucci
• Feasting like royalty on seafood linguine, mussels and antipasto platters
• Checking out celebrity homes and potential famous face sightings!

Orvieto: Dramatic Hilltop Refuge

Perched precariously atop a volcanic rock outcropping overlooking vineyards producing famous Orvieto Classico wine. The Umbrian city of Orvieto initially drew me in with its dramatically beautiful setting. Beyond photo ops with the imposing mottled stone Gothic Orvieto Cathedral dominating town. I fell in love wandering down cobblestoned alleys, stepping inside cool subterranean escape routes and shopping for unique handmade ceramics.

Things You Can’t Afford to Miss

• Taking the funicular up to town for heavenly views (so much better than driving!)
• Exploring more than just the front of Orvieto’s ornately carved cathedral facade to see famous frescos inside
• Going underground into Orvieto’s fascinating Etruscan cave network
• Sampling the famous Classico wine produced in vineyards dotting the surrounding countryside
• Bringing home modern takes on traditional Umbrian ceramics from local artisans

Venice: Italy’s Floating Fairytale City

It’s impossible to talk about Italy’s beauty without paying homage to magical Venice, whose elaborate Gothic palaces seem to rise straight from the sea. As the famous destination continues drawing crowds by the millions. I recommend venturing away from bustling Piazza San Marco to uncover a maze of nearly car-free cobblestoned alleyways opening onto countless postcard-worthy canal views showcasing gondolas drifting by historic bridges and waterside cafes.

My Venice Must-Do’s

• Getting intentionally lost down alluring back streets in Dorsoduro or Cannaregio neighborhoods
• Experiencing the easy pace of Venetian life sipping cappuccinos canal-side as water taxis sputter by
• Exploring centuries-old palazzos filled with artistic masterpieces now protected as museums
• Eating my weight in seafood, pasta, wine and italian sweets!

Burano – Kaleidoscope of Colorful Islands

Like confetti tossed whimsically across the northern Venetian lagoon, Burano easily outshines the already technicolored canal city with its chorus line of cottages in every shade imaginable. Of course I found rows of vibrantly hued fishermen’s homes reflected in aquamarine waters impossibly picturesque. But beyond Burano’s Instagram appeal, local lacemaking traditions, sleepy island pace . And the immense pride its residents have for their homes’ cheery facades charmed me completely.

Things to Do on Burano

• Exploring the pastel houses with an aperitif in hand, snapping endless photos
• Witnessing expert artisans stitching intricate Venetian lace patterns passed down for centuries
• Sampling fresh seafood right off the dockside boats from the lagoon
• Bringing home Burano’s iconic rainbow as hand-painted ceramic souvenirs

Pienza – Writer’s Muse & Cheesemaker’s Dream

It won’t take more than a quick stroll through the neat-as-a-pin lanes of Pienza .Before you note why UNESCO protects this tiny Tuscan hill town, considered the “ideal Renaissance town.” From its harmoniously designed architecture and sweeping valley views dotted with cypress trees to some of Italy’s best pecorino sheep’s cheese, Pienza utterly seduced me.

Beyond Pienza’s beauty and small town charm, some of my favorite moments came from connecting with locals passionate about sharing insight into their lives. I’ll never forget one shepherd recounting boyhood memories of his grandfather making traditional pecorino.

Must-Do’s in Pienza

• Joining locals in the piazza for the evening passeggiata tradition under the glow of the setting sun
• Sampling famous pecorino sheep’s milk cheese at farms passed down for generations
• Exploring the Pope Pius II’s 15th century papal palace residence
• Buying local honey, olive oil and wine to take home
• Eating at an agriturismo farm-to-table restaurant nearby

FAQS

What is the prettiest town in Italy?

While beauty is subjective, Positano is often considered one of if not the prettiest towns in Italy. Also given its pastel cliffside homes cascading down to the sea on the gorgeous Amalfi Coast. Cinque Terre and its string of colorful fishing villages along the cliffs of the Italian Riviera also tops many travelers’ lists.

What is the most beautiful town in Tuscany?

It’s impossible to identify just one most beautiful town in Tuscany! Between walled gems like San Gimignano, the iconic landscapes of Val d’Orcia, and charming hill towns like Pienza. you’ll discover picture-perfect scenes around every corner. Leaning away from larger cities, my personal vote for Tuscany’s most beautiful town goes to the small walled village of Monteriggioni. With its medieval towers and vineyards views.

What are the most beautiful places to visit in Italy?

While famous cities are must-sees, some of Italy’s most beautiful places are actually found in smaller countryside towns and villages like:

• The pastel cliffside villages of the Cinque Terre
• Charming hill towns of Tuscany and Umbria like Assisi, Montepulciano, and Montalcino
• The seaside towns of the Amalfi Coast such as Positano, Amalfi, and Ravello
• Italy’s beautiful lakes including Lake Como, Lake Garda, and Lake Maggiore

What is the most colorful town in Italy?

Hands down, Burano easily claims the title as Italy’s most colorful town! Located just a short boat ride from Venice in the lagoon, Burano is famous for its technicolor fishermen’s cottages freshly painted in every shade imaginable. You’ll swear someone cranked the saturation dial walking down the picture-perfect streets!

Are small towns in Italy safe?

Having traveled extensively through Italy myself, I can confidently say small towns in Italy are very safe to visit. Violent crime is extremely rare, especially in rural areas and away from larger cities. Of course, use common sense precautions as you would anywhere. The biggest annoyances travelers may encounter are pickpockets targeting crowded tourist sites or petty crimes like luggage theft if valuables are left unattended. Overall though, Italy’s charming small towns provide very welcoming, safe destinations to experience la dolce vita!