Having visited numerous Italian towns, I must admit that it’s nearly hard to locate one that is especially awful. These charming communities are like wine: plentiful and rarely disappointing. There are always some exceptions, though. And now I present to you these nine small Italian towns, carefully considered in terms of beauty, activities, food, and personality. Every one of them is captivating enough to make you want to tear up your ticket and throw your phone into the ocean as soon as you snap a final Instagram photo of the cliffside sunset.
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Positano
3,950 people live there.Notoriety claim: In 1953, John Steinbeck wrote a rhapsody about it. An essay in Harper’s Bazaar: “Positano goes deep.” It’s a surreal location that seems unreal while you’re there yet beckons you to stay after you leave.
It would be unimaginable to travel to Italy and not stop at the Amalfi Coast—that is, to consume five pounds of pasta a day. Positano, a cliffside village whose ostentatious guests shouldn’t put you off, might be the crown jewel of the whole coast. Enjoy instead the many citrus trees, the famed tiled dome of the Chiesa di Santa Maria Assunta church, and the small, twisting alleys dotted with stores offering handcrafted sandals and pottery (the town is especially well-known for its talented craftsmen). There’s a reason the wealthy come here.
San Gimignano
8,000 people live there.Fame claim: This is where Franco Zeffirelli filmed scenes with Mussolini for Tea.
This town’s 14 towers are all within its boundaries, and they all date back to the 1200s. If Tuscany had a downtown lined with highrises, this would be it. The once thriving mediaeval hilltop town, only a short day trip from Florence, is said to have been largely destroyed by a plague in the 1300s, but these days it’s a must-see in rural Tuscany. It truly feels like you are walking through time as you ascend the steps to the city. Undoubtedly, the most breathtaking sweeping view of the Chianti region awaits you once you reach the summit of the towers.
Barga
10,000 people live there.Summertime opera and jazz events are a claim to fame.
The principal town of the medium valle, or mid valley, in the province of Lucca is a wine country hilltop Renaissance town known as a “Venice without water.” I was fortunate enough to really stumble into the village of Barga in this area (a lot of cobblestone!). With its dimly lighted dark stone buildings and charming merchant workshops around every corner, it almost has a Hogwarts feel to it. If you do decide to visit, Trattoria L’Altana Barga offers about the most authentic Tuscan lunch you will find. Barga’s food is also so delicious that it’s frightening.
Vernazza
1,200 people live there.The streets are steep and there are almost no cars. This is their claim to fame.
Cinque Terre, or “five towns” in Italian, might be the closest thing to heaven, regardless of your belief in its existence. The five seaside communities offer fantastic views of the Mediterranean and are connected by strollable mountain roads that meander through vineyards. The most picturesque, or at least the most pleasant, is Vernazza. If you decide to hike there, you will descend into the town, which is dotted with rowboats lining the lake and houses coloured pink, yellow and blue. The village is tucked away like an Easter egg in a small cove next to the sea. Known as one of the most popular fishing villages on the Italian Riviera, it’s a great place to refuel with plenty of wine, fresh catches, and mussels.
San Teodoro (Sardinia)
There are 4,000 people living there.The views of the neighbouring island Tavolara, an impressive cliff face made of limestone, are its claim to fame.
La Cinta beach is one of the most picture-perfect crescents of sand anywhere; it puts other beaches to shame. It appears to have been built in Downtown Disney because it is almost too lovely. Its smooth white sand, however, does indeed exist, softly sloping into the warm, gin-clear ocean. It’ll be difficult, but if you can manage to get away from this sunny playground, this town is also excellent for boating, water skiing, horseback riding, and mountain hikes. After midnight, the tourist-friendly Downtown comes alive with activity, making it the ideal place to enjoy a Sardinian mirto or limoncello while people-watching.
Claudio Giovanni Colombo/Shutterstock
Castelluccio
Population: Fewer than 300Claim to fame: A summertime flower festival.
Land in this breathtaking mountaintop town and you’ll start cackling “poppies … POPPIES” like the Wicked Witch of the West. The reason: a massive field of flowers (including, yes, poppies) like something from Oz. The season from May to June here is called “flowering” season, but if you miss it, you’re still in for scenery: as the highest village the Apennine Mountain Range, at 5,000ft above sea level, Castelluccio is also bordered by snow-capped mountains.
Cefalù (Sicily)
Population: 14,000Claim to fame: The Cathedral-Basilica of Cefalù, an UNESCO World Heritage church with Norman and Arab influences.
Holy flipping sunset, Batman! This Sicilian beach town is what #nofilter shots are made of, with something prettier than the next at every turn. Sicily feels completely different than the rest of the country — and that’s because it used to actually be its own country. The white sand beaches and crystal clear waters are reminiscent of Greek isles, except with that same Italian charm — and same awesome food.