Italy is so much more than just Rome, Florence, and Venice. Tucked into the hills, perched on cliffs, and scattered along the coast are charming little villages that feel like they’re straight out of a storybook—where time moves slower, the views take your breath away, and everything feels a little bit magical.
Love charm, history, and places with a little magic? Don’t miss these 15 enchanting Italian towns.
I earn a small commission when you book through these links, which help run this blog.
Civita di Bagnoregio – Lazio
The “Dying City.” Accessible only by a dramatic footbridge, this ancient Etruscan town perched precariously on volcanic rock feels like an island in the sky. Its silent, car-free lanes and crumbling facades are hauntingly beautiful. Stay nearby in Bagnoregio and visit early or late to avoid crowds.
Manarola – Cinque Terre, Liguria
Cinque Terre is pure magic, but Manarola is arguably its most iconic postcard scene. Candy-colored houses cascade down a sheer cliff face into a tiny harbor. Hike the Sentiero Azzurro for breathtaking views, sip Sciacchetrà wine, and soak in the vibrant sunset hues.
San Gimignano – Tuscany
The “Medieval Manhattan.” Its skyline, punctuated by 14 surviving stone towers, transports you instantly to the 13th century. Wander the perfectly preserved Piazza della Cisterna, savor world-renowned gelato, and gaze out over the rolling Tuscan hills.
Stay: For a truly atmospheric experience within the walls, consider the elegant Hotel L’Antico Pozzo, set in a converted medieval palace.
Alberobello – Puglia
Prepare for architectural whimsy! This UNESCO site is famous for its trulli – unique whitewashed, conical-roofed houses that look like something hobbits might inhabit. Getting lost in the Rione Monti district is pure delight.
Stay: Sleep IN a trullo! Options range from simple B&Bs (Trulli Holiday) to luxurious restored clusters (like Trulli e Puglia Resort).
Matera – Basilicata
A city carved from stone. The ancient Sassi districts (cave dwellings) are one of the world’s oldest continuously inhabited settlements. Exploring the labyrinthine streets, cave churches, and modern revitalizations is an unforgettable journey through time.
Stay: For ultimate immersion, book a cave hotel. Sextantio Le Grotte della Civita offers an exceptionally atmospheric and luxurious cave experience.
Orta San Giulio – Piedmont
Overlooking the serene Lake Orta, this is Italy’s hidden lake gem. The main square, Piazza Motta, opens onto the lake with views of the enchanting Isola San Giulio. Charming lanes, ornate villas, and a slower pace define this fairy-tale setting.
Positano – Amalfi Coast, Campania
The vertical dream. Pastel houses tumble down the mountainside towards the sparkling Tyrrhenian Sea in a breathtaking cascade. Wander its steep, flower-filled lanes, shop for linen, and watch the world go by from a cliffside café.
Stay: Experience iconic glamour at Le Sirenuse, a legendary family-run hotel with panoramic views and impeccable style.
Sabbioneta – Lombardy
A Renaissance “Ideal City.” Planned by Vespasiano Gonzaga in the 16th century, its perfect geometric layout, star-shaped walls, and harmonious piazzas (like the Teatro all’Antica, one of the world’s oldest surviving theaters) feel like walking through a living architectural blueprint.
Castelmezzano – Basilicata
Nestled dramatically within the jagged Lucanian Dolomites, this village clings to the rocks like an eagle’s nest. Its stone houses blend seamlessly with the mountain. Hike the challenging “Flight of the Angel” zip-line path or simply marvel at the incredible natural setting.
Montefioralle – Tuscany
Tucked above the vineyards of Greve in Chianti, Montefioralle isn’t just pretty—it’s perfect. Imagine a tiny, circular village entirely enclosed by 14th-century walls, where no cars disturb the silence. Its concentric rings of honey-colored stone houses, terracotta roofs, and flower-draped doorways feel suspended in time. This is where Amerigo Vespucci’s family once lived, and the atmosphere remains deeply authentic.
Stay Nearby: While no hotels sit inside the hamlet, the surrounding Chianti countryside offers gems. Try Agriturismo Montefioralle (5-min walk) for rustic rooms and pool views over olive groves. Or splurge at nearby Castello di Verrazzano, a working winery castle.
Castelluccio – Umbria
For a different kind of magic. Perched high in the Sibillini Mountains, it overlooks the Piano Grande plateau. Visit in late spring/early summer for the legendary Fioritura (blooming) when the valley explodes in a kaleidoscope of wildflowers – a natural fairy tale spectacle.
Erice – Sicily
A mystical hilltop town above Trapani. Cobbled streets wind past Norman castles, ancient churches, and stunning gardens. Often shrouded in mist, its atmosphere is ethereal. Don’t miss the famous almond pastries! Visit Pasticceria Maria Grammatico—try genovesi (sweet ricotta pies) made using medieval convent recipes, or see the Chiesa Matrice’s Gothic portal and its separate bell tower (once a watchtower).
Sleep like a medieval scholar at Hotel San Domenico, a restored 15th-century monastery with cloisters and sea views. Or opt for Erico Hotel, where rooms have Trapani Bay panoramas.
Portofino – Liguria
Glamorous, yes, but undeniably storybook. The iconic Piazzetta, lined with colorful houses and luxury yachts bobbing in the tiny harbor, is pure Mediterranean fantasy. Hike to the Brown Castle for panoramic views. (Be prepared for exclusivity).
Grottammare – Le Marche
Often overlooked, this Adriatic gem boasts a stunning medieval upper town (“Paese Alto”) with imposing walls, ancient gates, and panoramic sea views. Below, a charming seaside promenade and beach offer a delightful contrast.
Dozza – Emilia-Romagna
The “Painted Town.” Its historic center is an open-air gallery, with houses adorned by vibrant murals created during the biennial festival. Wandering its streets is like stepping into a living, breathing art installation.
Every two years, artists transform its walls into an open-air gallery during the Biennale del Muro Dipinto (Painted Wall Biennial). Centuries-old buildings become canvases for surreal murals, creating a kaleidoscopic walk through history and fantasy. Even the Rocca’s dungeon has art! Visit the Rocca Sforzesca castle—its cellars house Enoteca Regionale, where you can taste 1,000+ Emilia-Romagna wines. For true immersion, book La Rocca Suite inside the castle itself—stone arches, frescoed ceilings, and breakfast in a medieval hall.
Read next: Top 20 Most Beautiful Villages Which Came Straight Out Of Fairytales
Pin this post to save it for later!
