The most magical Italian moments don’t come from ticking off major landmarks, but from wandering winding alleys, sipping espresso in silent piazzas, and stumbling upon ancient ruins without a soul in sight.
Rome, Venice, Florence… iconic, unforgettable, and—let’s be honest—overcrowded. But what if the most magical Italian moments don’t come from ticking off major landmarks, but from wandering winding alleys, sipping espresso in silent piazzas, and stumbling upon ancient ruins without a soul in sight?
That’s the beauty of Italy’s small towns—and they’re exactly where MyGuideGuru shines. With AI-powered, self-guided walking tours available anywhere, you can ditch the crowd and discover stories, secrets, and scenery that most tourists never see.
Here are our top picks for small towns inItaly that offer rich history, stunning views, and unforgettable walks—without the chaos.
Once overlooked, Matera is now one of Italy’s most fascinating hidden gems. Its ancient cave dwellings—the Sassi—are carved directly into limestone cliffs and tell the story of over 9,000 years of human settlement. Make sure you don’t miss the view at sunset from Belvedere di Murgia Timone!
Sitting atop a dramatic volcanic cliff,Orvieto offers medieval architecture, underground tunnels, and sweeping countryside views—all in a single, walkable loop. Most visitors zoom pastOrvieto en route to Rome or Florence. Their loss!
Known as “Little Jerusalem,” Pitigliano’s winding stone streets and mysterious Etruscan pathways are steeped in Jewish and Roman history. A walking tour here is part history lesson, part nature hike—with views across lush Tuscan valleys and cliffs. Don’t leave without trying the sfratto, a traditional Jewish pastry unique to this region.
Ascoli is all golden travertine and Gothic arches, but somehow it hasn’t made it to most guidebooks. You can stroll from the Piazza del Popolo to medieval towers and Roman bridges, with hardly another tourist in sight. This is also the birthplace of the olive all’ascolana—deep-fried, stuffed olives. Yes, please.
A whitewashed seaside town perched on limestone cliffs over the Adriatic, Polignano is postcard-perfect—minus theInstagram mobs. It’s the hometown of singer Domenico Modugno (“Volare”), and walking tours here blend history with music, sea breeze, and gelato. Make sure to hit the cliffs at golden hour.
The birthplace of Roman poet Ovid, Sulmona isa town of romantic architecture, ancient aqueducts, and slow, authentic Italian life. The town surrounded by stunning national parks if you want to extend your stay. It’s also the confetti (sugar almond) capital of Italy!
Italy’s “perfect Renaissance city,” Sabbioneta was built from scratch in the 16th century to be the ideal urban centre—and remains beautifully preserved. This town is ideal for architecture buffs, allowing you to explore the perfectly symmetrical layout, theatres, and gardens in a quiet, peaceful setting.
With MyGuideGuru, every town becomes a treasure hunt—no matter how big or small. Our AI-powered tours let you:
Italy’s small towns are where you’ll find its heart. And now, with just your phone and a good pair of shoes, you can explore them like a local… or better yet, like a time-traveller.
Rediscover your love of travel. Know the story behind the photos. Start exploring the real Italy today—with MyGuideGuru. Download the app and get off the beaten path.
