Italy is one of those places everyone claims to “know.” Pizza? Check. Pasta? Sure. Gelato? Obviously. But here’s the secret nobody tells you: Italy is weird. Italy is magical. Italy is full of tiny, unexpected moments that don’t make it into glossy brochures but absolutely should.

If you’ve ever fantasised about living your best European-main-character life, these quirky, breathtaking, and “wait—Italy has THAT?” experiences will shake up your bucket list in the best possible way.

Grab your Aperol, babes — we’re going in.

1. Swim in a Roman emperor’s private grotto

Yes, you can literally splash around in a cave that once belonged to Emperor Tiberius. Hidden along the Campania coastline, Tiberius’ Grotto looks like something straight out of a fantasy novel — glowing turquoise water, shimmering stone walls, and pure drama.

For the history girlies, National Geographic has an amazing deep-dive into Italy’s hidden coastal ruins. It’s the perfect pre-trip rabbit hole.

2. Sleep inside Puglia’s fairytale trulli

Forget hotels — stay in a trullo, Italy’s iconic stone cottages with pointy, cone-shaped roofs that look like a hobbit home designed by a minimalist influencer.

You can find the cutest, bougiest stays on Booking.com or scroll inspo on The Culture Trip’s Puglia guide.

Bonus: They photograph beautifully.

3. Explore Italy’s “ghost villages”

Italy has entire abandoned villages frozen in time — quiet, cinematic, a little spooky, and ridiculously photogenic.

• Craco (Basilicata) — so hauntingly beautiful it’s been used in multiple films
• Bussana Vecchia (Liguria) — now an artist’s community with open studios
• Pentedattilo (Calabria) — shaped like a giant stone hand

Check out Atlas Obscura’s ghost town list for an addicting scroll.

4. Truffle hunting with trained dogs

Imagine wandering through misty forests in Tuscany with a truffle-sniffing dog that’s worth more than your last three paychecks. It’s chaotic, hilarious, earthy, and ends with truffle-covered pasta that tastes like actual heaven.

If you want a legit experience, Walks of Italy and GetYourGuide have great options.

5. Bologna’s secret canals — the city Venice doesn’t want you to know about

Behind one tiny wooden window — La Finestrella — lies a secret canal that gives you surprise-Venice vibes without the crowds, pigeons, or €12 cappuccinos.

Pair your canal stroll with a plate of authentic ragu.
Eater has the best Bologna food map for planning your carb crawl.

6. Learn to cook in a real Italian home

One of the most heart-melting experiences in Italy? Joining a cooking class inside someone’s actual kitchen. You’ll roll pasta by hand, make sauces from scratch, and get fed like you’ve been unofficially adopted.

Find real local classes on Airbnb Experiences — the ones hosted by nonnas are life-changing.

7. Sip wine from Florence’s tiny “wine windows”

During the plague years, Florence used mini wine windows (buchette del vino) to sell wine safely. Guess what? They’re back — and you can buy a glass of Chianti through a tiny medieval door like a Renaissance queen.

For a history fix, read The Guardian’s piece on wine windows — it’s surprisingly fascinating.

8. Hike the Path of the Gods on the Amalfi Coast

It sounds dramatic because it is. The Sentiero degli Dei runs along the cliffs above the Amalfi Coast with scenery so stunning it borders on rude.

Even non-hikers can manage it, and the views are next-level.
Conde Nast’s Amalfi hiking guide gives a perfect visual preview.

9. Visit Rome’s mind-bending illusion church

Inside Chiesa di Sant’Ignazio, the giant dome isn’t a dome at all — it’s a flat painting. You step forward… it disappears. Step back… it comes alive. It’s basically a Renaissance optical illusion.

For art lovers, My Modern Met has a whole feature on Italy’s best illusion art.

10. Escape to Italy’s “secret islands”

Italy has more islands than most travellers realise — and some are blissfully under the radar.

Try:
• Ponza — pastel houses + water so clear it looks filtered
• Marettimo — wild, rugged, and almost empty
• Procida — the real-life version of a pastel dream

For serious wanderlust, browse Lonely Planet’s Italy islands guide.

Why Italy’s unexpected side is the best side

Italy isn’t just landmarks and pasta. It’s caves glowing like sapphires, ghost villages sleeping on hilltops, wine windows, pasta lessons, secret islands, and little slices of magic you discover when you wander off the brochure-approved path.

It’s the Italy that stays with you — the one that takes your trip from “nice holiday” to “core memory.”