GemmaItaly is more than just pizza, pasta, and gelato—though those are compelling reasons to visit. If you dig a little deeper, you’ll find towns that look like they’ve been plucked straight from storybooks. Cobblestone streets, pastel-colored houses, and charming piazzas await, each corner hiding a secret waiting for you to discover. From my own personal experience, wandering through these towns feels like stepping into a painting you can walk through, where every detail is curated by centuries of history, culture, and a touch of whimsy.
Whether you’re planning your next vacation, looking for hidden gems off the usual tourist radar, or simply daydreaming about wandering under sun-drenched Italian skies, these ten towns will captivate you. Here’s a guide to fairytale towns in Italy you truly need to see.
1. Civita di Bagnoregio – The Dying Town That Refuses to Fade
Civita di Bagnoregio is often called “The Dying Town” because it sits atop a hill slowly eroding away. Don’t let that scare you—this town is alive with charm. You reach it via a pedestrian bridge, which instantly makes you feel like you’re entering another world.
The town itself is small, but its beauty is colossal. Every street feels like it was designed to be photographed. The stone buildings, tiny cafes, and breathtaking panoramic views over the valleys make it a dream for photographers and romantics alike.
Things to do: Explore the old churches, enjoy a slow coffee while gazing over the valley, and wander through streets so narrow you might bump into history itself. From my own personal experience, arriving early in the morning is magical—the light hits the town just right, and you feel like you’re the only person there.
2. Alberobello – Where Trulli Houses Make You Gasp
Alberobello is the kind of place that makes you question reality. Its unique trulli houses—cone-shaped, whitewashed stone huts—look like they came straight out of a children’s book. Walking through the Rione Monti district, you’ll feel like you’ve stepped into a gingerbread village.
Beyond its looks, Alberobello has history baked into its walls. The town has managed to preserve its trulli architecture for centuries, offering a rare glimpse into Italian rural life.
Things to do: Wander the maze-like streets, snap photos of the intricate stonework, and pop into local shops to buy handcrafted souvenirs. If you’re lucky, you might catch a festival showcasing traditional music and food, making your visit even more enchanting.
3. San Gimignano – The Town of Towers
San Gimignano is often called the “Medieval Manhattan” because of its striking skyline dotted with towers. Once, over seventy towers defined its silhouette, but today, fourteen remain. These medieval towers give the town an unmistakable character and charm.
Walking through San Gimignano is like stepping back to the Middle Ages. You can almost hear the clatter of horse hooves and smell the bread baking in medieval ovens. And let’s not forget the gelato—San Gimignano is home to some of the best in Italy.
Things to do: Climb Torre Grossa for a panoramic view of the Tuscan countryside, visit the Collegiate Church with its medieval frescoes, and sample local wines and gelato at family-run shops. Based on my overall experience, trying gelato while strolling through the cobbled streets feels like the ultimate Italian indulgence.
4. Positano – Cliffside Beauty on the Amalfi Coast
Positano is that postcard-perfect town perched on cliffs above the Tyrrhenian Sea. Its cascading pastel houses, narrow stairways, and bougainvillea-draped balconies make it instantly romantic.
The town is a haven for those who love the sea and the sun. Beach lovers will enjoy the small Spiaggia Grande, while art and culture enthusiasts will delight in boutique galleries and vibrant local craftsmanship.
Things to do: Wander the steep streets lined with chic boutiques, relax on the beach, or take a boat tour along the coast. From my own personal experience, arriving in Positano just before sunset creates a magical light that makes the town glow as if it’s alive.
5. Monte Isola – Italy’s Island Gem
Monte Isola, the largest lake island in Europe, sits quietly in Lake Iseo. Unlike the Amalfi Coast’s bustle, Monte Isola offers peace and serenity. It’s a town where cars are few, bicycles and boats are many, and life feels delightfully slow.
Walking through the cobbled streets, you’ll discover local fishermen, artisan shops, and small trattorias serving fresh lake fish.
Things to do: Rent a bike or take a boat ride around the island, hike to the sanctuary at the top for panoramic views, and enjoy a lakeside meal. Based on my overall experience, Monte Isola is perfect for a quiet retreat where you can breathe and savor the simple pleasures of Italy.
6. Portovenere – The Jewel of Liguria
Portovenere is often overshadowed by Cinque Terre, but it’s a gem in its own right. The town sits at the tip of a peninsula, with colorful houses perched along the waterfront. Its dramatic castle, medieval streets, and the nearby island of Palmaria make it unforgettable.
The town feels like a painting, especially when seen from the sea. Walking its narrow lanes is a journey through history, with every corner offering a new perspective of the Ligurian coast.
Things to do: Explore the Doria Castle, stroll along the waterfront promenade, and take a boat trip to nearby islands. From my own personal experience, visiting Portovenere early in the morning before the crowds arrive lets you experience its serene beauty almost privately.
7. Vernazza – Cinque Terre’s Heartbeat
Vernazza is the kind of town that captures your heart instantly. Tiny harbor, pastel-colored houses, and cliffs plunging into the sea—Vernazza is quintessential Cinque Terre.
Life here revolves around the sea. Boats bob in the harbor, fishermen sell their catch, and trattorias serve dishes that taste of the ocean.
Things to do: Hike the trails connecting Vernazza to other Cinque Terre towns, relax in the harbor square, and savor freshly caught seafood. Based on my overall experience, hiking to Vernazza from nearby trails gives you perspectives that postcards can’t capture—views that are breathtaking in real life.
8. Burano – Venice’s Rainbow Island
Burano is a riot of colors. Every house is painted in a vibrant hue, creating a rainbow effect that’s impossible to ignore. Beyond its visual appeal, Burano is famous for its lace-making tradition, a craft passed down for generations.
Walking through Burano, you’ll find canals reflecting the colorful buildings, small cafes, and artisan shops tucked into every corner.
Things to do: Photograph the colorful streets, watch local lace-making demonstrations, and enjoy seafood dishes by the canal. From my own personal experience, wandering without a map allows you to stumble upon hidden corners where locals live, adding a sense of authenticity to your visit.
9. Orta San Giulio – Tranquil Lakeside Beauty
Orta San Giulio, on Lake Orta, feels like a town designed for peace. Its medieval streets, charming piazzas, and the small island of San Giulio just offshore make it perfect for a slow wander.
The town is less crowded than nearby Lake Como, offering a more intimate experience of Italian lakeside life.
Things to do: Take a boat to San Giulio Island, explore the quaint streets, and relax in cafes by the lake. Based on my overall experience, visiting Orta San Giulio in the afternoon as the sun sets creates a golden glow that makes the town look like it’s from a dream.
10. Pitigliano – The “Little Jerusalem”
Pitigliano is a striking town built on tufa cliffs in southern Tuscany. Known as the “Little Jerusalem” for its historic Jewish community, it’s a town where history is layered in stone.
Walking through Pitigliano feels like walking on a stage set. The stone buildings, winding streets, and ancient aqueducts tell a story of resilience and beauty.
Things to do: Explore the old Jewish quarter, visit the ancient churches and synagogues, and wander the narrow alleys that seem to twist endlessly. From my own personal experience, Pitigliano is a place where history whispers to you as you explore, and every turn is a photo opportunity waiting to happen.
Why These Towns Will Capture Your Heart
Each of these towns has its own personality, charm, and story. From pastel houses to medieval towers, from serene lakes to cliffside views, Italy’s fairytale towns offer experiences that go beyond sightseeing—they invite you to slow down, explore, and immerse yourself in the beauty of everyday life.
Whether you’re chasing romance, history, photography opportunities, or just a place to breathe, these towns will deliver. They remind us that the magic of Italy isn’t just in its landmarks, but in the small corners where life continues, centuries-old traditions are preserved, and moments are lived beautifully.
So pack your walking shoes, bring your camera, and get ready to fall in love. From my own personal experience, Italy’s fairytale towns have a way of sneaking into your heart, staying there long after you’ve left, and tempting you to return again and again.
I’m Gemma, a passionate lifestyle blogger sharing my creative world with you. Gemitaliano.com is my little corner of the internet, glad you’re here.