GemmaItaly is a country where every corner seems to have a story. From sun-soaked piazzas to tucked-away alleys lined with centuries-old buildings, Italian streets have a charm that is simply irresistible. Whether you’re a seasoned traveler or planning your first Italian getaway, exploring the old towns is a must. From my own personal experience, wandering these streets feels like stepping into a living postcard. Each lane is a mix of history, culture, and moments waiting to be captured.
Italy isn’t just about the big cities like Rome, Florence, or Venice. Some of the most enchanting experiences happen when you get lost in the smaller towns, where every street has character, and every corner offers a surprise. Let’s take a walk together through 15 charming streets in Italian old towns that you truly need to see.
1. Via delle Volte – Lucca
Lucca is often overshadowed by Florence and Pisa, but its medieval streets are worth every moment. Via delle Volte is a narrow, covered alley that makes you feel like you’ve traveled back to the Renaissance. The street’s low archways and stone walls create a unique atmosphere. You can almost hear merchants from centuries ago calling out their wares. Walking here is peaceful, yet it teases you with glimpses of hidden gardens and courtyards.
2. Via Giuseppe Garibaldi – Portovenere
Portovenere, a quaint town on the Ligurian coast, is full of colorful houses clinging to cliffs. Via Giuseppe Garibaldi runs along the waterfront, offering views of boats bobbing in the harbor. From my overall experience, early mornings here are magical—the soft light hitting the pastel facades makes it feel like a painting come to life. Cafés line the street, perfect for a slow Italian breakfast.
3. Via del Bacio – Verona
If you’ve ever dreamed of romance, Via del Bacio in Verona might just make your heart flutter. Named “Street of Kisses,” it’s a small, charming alley near Juliet’s balcony. Cobblestones, ivy, and historic buildings create a perfect backdrop for a romantic stroll. Tourists flock here, but arriving early gives you the chance to enjoy the street almost to yourself. Bonus: it’s a great spot for photos that scream “Italy.”
4. Via Toledo – Naples
Naples’ Via Toledo is vibrant, chaotic, and unforgettable. It’s not just a street; it’s an experience. From bustling markets to street performers and historic cafes, every step tells a story. Based on my overall experience, this street captures the real, raw spirit of Naples. Grab a slice of authentic Neapolitan pizza and watch the world go by—it’s impossible not to get caught up in the energy.
5. Via San Gimignano – San Gimignano
San Gimignano is famous for its medieval towers, and Via San Gimignano runs right through the heart of it. This street is lined with gelaterias, artisan shops, and historical buildings. Walking here is like following a trail of Tuscany’s best highlights. From my own personal experience, stopping in a small café and sipping a cappuccino while watching tourists and locals mingle is a simple pleasure you won’t forget.
6. Via Roma – Taormina
Sicily’s Taormina is known for its stunning views of Mount Etna and the sea. Via Roma is the town’s main street, and it’s a perfect mix of luxury boutiques and traditional shops. The street curves along the hillside, revealing breathtaking glimpses of the coastline. Wander slowly, peek into artisan stores, and don’t forget to try some Sicilian pastries—they’re divine.
7. Via Margutta – Rome
Rome is full of iconic streets, but Via Margutta offers a quieter, artsy experience. Historically, it was home to artists and craftsmen, and today it still retains that bohemian vibe. Art galleries and small cafes line the street, and it’s perfect for a slow, thoughtful stroll. From my overall experience, this is one of the best spots to feel Rome beyond the usual tourist attractions.
8. Via San Lorenzo – Florence
Florence has plenty of famous streets, but Via San Lorenzo is where life pulses with authenticity. Near the Mercato Centrale, it’s filled with stalls, small shops, and food vendors. The aromas of fresh pasta, cured meats, and pastries make it a feast for the senses. From my own personal experience, taking a few hours to explore the backstreets here is more rewarding than sticking only to the main squares.
9. Via dei Fori Imperiali – Rome
If you want a street that’s history in motion, Via dei Fori Imperiali is it. Lined with the ruins of ancient Rome, this wide avenue stretches between the Colosseum and Piazza Venezia. Walking here feels like time travel. Tourists might crowd the street, but its sheer scale and historical weight make every step memorable. Pausing to imagine gladiators and Roman citizens crossing the same path adds a thrilling perspective.
10. Via dello Stradone – Siena
Siena is famous for its Palio horse race, and Via dello Stradone gives you a slice of that medieval charm. The cobblestones, brick facades, and occasional flower boxes make it picture-perfect. Walking slowly allows you to appreciate small details—the intricate doors, wrought-iron balconies, and glimpses into local shops. From my overall experience, Siena’s streets feel like a living museum.
11. Via Garibaldi – Genoa
Genoa’s Via Garibaldi is all about elegance. It’s part of the UNESCO-listed Palazzi dei Rolli, a series of historic palaces. Walking here feels like being in an open-air art gallery. You’ll notice the elaborate doors, frescoed facades, and grand architecture that tells stories of wealthy Genoese families. If you’re a history lover, this street is a treasure trove.
12. Via Capodiferro – Bologna
Bologna is famous for its porticoes, and Via Capodiferro showcases them beautifully. Strolling under the covered walkways, you’ll find boutique shops, cafés, and bookstores. The street is lively yet cozy, and its medieval charm is palpable. Based on my overall experience, this is a great street to combine shopping, people-watching, and appreciating Bologna’s unique urban style.
13. Via Santa Maria – Trani
Trani, a coastal gem in Puglia, offers Via Santa Maria, a street lined with historic buildings and cafes. The harbor is close by, and the views of the cathedral against the Adriatic are breathtaking. From my own personal experience, exploring this street during sunset is magical—the golden light brings every stone and building to life.
14. Via della Costa – Cinque Terre
Cinque Terre’s charm is impossible to miss, and Via della Costa is one of its most picturesque streets. It winds through colorful houses, small shops, and scenic viewpoints. Hiking between villages gives you a sense of adventure, and this street feels like a reward for your efforts. The combination of sea views, vibrant colors, and local life makes it unforgettable.
15. Via Giuseppe Garibaldi – Alghero
Sardinia’s Alghero is a mix of Italian and Catalan influence, and Via Giuseppe Garibaldi reflects that. Cobbled streets, pastel-colored buildings, and flower-filled balconies create a romantic atmosphere. Walking here feels relaxed, and stopping at a café for a local pastry is a perfect way to soak it all in. From my overall experience, Alghero’s streets are underrated gems for anyone exploring Italy.
Final Thoughts
Exploring Italy’s old towns is more than a sightseeing trip; it’s an experience of life itself. These 15 charming streets give you a taste of Italy’s rich history, vibrant culture, and everyday beauty. From colorful alleys to historic avenues, each street offers something unique, whether it’s food, art, architecture, or simple moments of peace.
If you take anything from this guide, let it be this: wander slowly, look closely, and don’t rush. Italy’s charm is in the details, and these streets are proof that the journey matters just as much as the destination. Trust me, you’ll want to return to these streets 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.