I Let AI Plan My Italy Trip—Here’s the Bizarre 3-Day Itinerary That Went Viral (And How You Can Do It Better)

Picture this: You’re sipping Chianti in a 15th-century Tuscan castle, its stone walls echoing with tales of mediaeval knights—and you’re paying less than you would for a bland hotel chain. Sounds like a fantasy, right? Trust me, I thought so too—until I handed my Italy trip to an AI and ended up in a haunted suite, a pesto-making village, and a secret Venetian gondola route without a single tourist in sight. Let’s rewrite the rulebook on Italian travel. Spoiler: No crowds, no compromises, and definitely no overpriced gelato.

Italy’s charm is drowning in overtourism. The Colosseum? A sea of selfie sticks. Venice’s canals? More crowded than Times Square on New Year’s Eve. And those “must-see” itineraries? They’re recycled lists that stick you in €300/night hotels with all the personality of a spreadsheet. But here’s the kicker: You don’t have to choose between luxury and authenticity. The secret? Let AI do the heavy lifting—with a few human tweaks.

Three non-negotiable rules for 2025:

No Crowds: Swap postcard clichés for villages even Italians forget about. Here are some of Italy’s Best-Kept Secrets (And How to Find Them) Forget the Classics. Let’s talk real Italy:

• Civita di Bagnoregio (Lazio): Dubbed “The Dying Town,” this crumbling mediaeval gem sits atop a volcanic cliff. With only 10 full-time residents, you’ll wander cobblestone streets alone at sunrise. Pro tip: Take the 8:05 AM Cotral bus from Viterbo (€2.50) to beat day-trippers.

• Borgomaro (Liguria): A hilltop hamlet where locals guard pesto recipes like state secrets. Book a cooking class with Nonna Maria (€20, includes lunch and endless wine). Her kitchen smells like heaven and looks like a 1950s postcard.

• Triora (Liguria): Italy’s “Witch Village” is a labyrinth of stone houses and eerie folklore. Visit Pasticceria Maccario for chestnut flour cookies—the owner, Lucia, claims her recipes are “blessed by the coven.”

How to replicate this:

Use AI tools like Wanderlog or Roam Around, but add filters: “under 1,000 annual visitors,” “local festivals,” and “no UNESCO sites.”

Avoid: Rome, Florence, and Venice between June and August. Instead, target April-May or September-October for shoulder-season serenity.

• OPTION 1: Castello di Casole (Tuscany)

Where mediaeval grandeur meets Tuscan luxury—without the mediaeval price tag (if you play it smart).

The Vibe: A 10th-century castle turned Relais & Châteaux gem, sprawling over 4,200 acres of vineyards and olive groves. Think infinity pools with countryside vistas, stone fireplaces big enough to roast a boar, and a Michelin-starred restaurant where even the bread feels like a luxury.

Best Room for Views: The Belvedere Suite. Floor-to-ceiling windows framing postcard-perfect Tuscan sunsets. Private terrace overlooking the estate’s vineyards (ideal for dramatic Instagram reels).

Best Room for Budget Travellers: The Classic Double Room “Budget” is relative here, but this is the castle’s entry-level option (€700+/night). Still includes access to the pool, bikes, and a breakfast spread fit for a Medici.

Secret hack: Book November-March for rates as low as €500/night (yes, that’s their “sale”).

Why It’s Worth the Splurge: Free truffle-hunting tours in the estate’s woods. Wine tastings in the 18th-century cellar (€50/person, but life-changing).

Your Takeaway: This isn’t just a hotel—it’s a time machine to Renaissance Italy (with Wi-Fi). Save up, book early, and live like Tuscan nobility, even if it’s just for one night.

• OPTION 2: La Francesca Resort (Liguria)

Where Mediterranean magic meets budget-savvy bliss—think cliffside cottages, olive groves, and a private beach that’ll make you forget the Amalfi Coast exists.

The Vibe: A family-run sanctuary perched above the Ligurian Sea, where lemon trees scent the air and Nonna’s recipes rule the kitchen. Think: rustic-chic cottages with hand-painted tiles, a hidden cove beach (no Instagram crowds), and sunset aperitivos served with homemade limoncello.

Best Room for Views: The Sea View Suite, Floor-to-ceiling windows framing the Cinque Terre coastline (yes, it’s that iconic). Private terrace with a daybed for lazy afternoons and stargazing nights.

Pro tip: Ask for Room 12—it’s tucked away for maximum privacy and has a secret staircase to the beach.

Best Room for Budget Travellers: The Garden Bungalow; Cosy, ivy-covered cottage steps from the resort’s organic garden (€120–€180/night). No sea view, but you’ll wake up to the scent of rosemary and the sound of cicadas.

Why It’s Worth the Splurge: The free perks are morning yoga on the cliffside deck, nonna-led pasta classes (yes, free), and unlimited garden-fresh snacks (think: sun-warmed tomatoes and focaccia). Private boat tours to Portofino for €80/hour (split with 4 friends = €20 each).

Budget Workaround: Can’t swing a stay? Day-pass the resort! Pay €25 for pool/beach access + a 3-course lunch at their trattoria (local catch pasta + limoncello tiramisu).

Your Takeaway: This isn’t a hotel—it’s a Ligurian family’s home (with a Michelin-trained chef and an infinity pool). Book early, pack stretchy pants, and prepare to eat your weight in pesto.

Budget-friendly AF: How to Live Large on a Backpacker’s Budget. Italy doesn’t have to cost €200/day. Here’s how I did it for €75:

Trains: Skip Frecciarossa. Regional trains (€8-15) are slower but scenic. Example: Florence → Lucca (1 hour, €8).

Eats: Avoid restaurants with English menus. Hit osterias instead:

• Osteria del Castello (Triora): chickpea pancakes with rosemary, €6.
• Trattoria Antico Forno (Civita): Wild boar ragù, €9.

Freebies: Join the passeggiata (evening stroll) in any village. Locals will drag you into wine tastings.

The AI’s 3-Day Itinerary (Hour-by-Hour Breakdown)

Day 1: Tuscany’s Haunted Hideaways

6:30 AM: Bus from Viterbo to Civita di Bagnoregio. Arrive by 8 AM to photograph the Bridge of Hope fog.

9:00 AM: Breakfast at Bar Peppone (€4 cappuccino + cornetto).

11:00 AM: Hike to Belvedere del Ponte for cliffside panoramas.

1:00 PM: Lunch at Trattoria Antico Forno (€10 ragù + house red).

3:00 PM: Check into Castello di Casole. Demand the ghost tour (free, but tip the guide €5).

7:00 PM: Dinner at the castle’s Tosca Restaurant (€25 for 4 courses—skip the wine list; your tasting covers it).

Day 2: Liguria’s Secret Villages

7:00 AM: Train to Borgomaro (€12, 2 hours).

9:30 AM: Pestò class with Nonna Maria (€20, 2 hours). Key move: Compliment her basil for extra wine.

12:30 PM: Lunch at her kitchen table: trofie al pesto, focaccia, and tiramisu.

2:30 PM: Bus to Triora (€3, 30 mins). Wander witch-themed alleyways.

5:00 PM: Check into La Francesca Resort. Beg chef Marco for his focaccia recipe (he’ll cave after limoncello).

8:00 PM: Dinner at Osteria del Castello (€12 pancake feast).

Day 3: Venice’s Unseen Canals

6:30 AM: Train to Venice (€25, 4 hours). Nap.

10:00 AM: Skip San Marco. Head to Squero di San Trovaso for a “secret” gondola ride (€40/30 mins—split with friends).

12:00 PM: Cicchetti at Cantina Do Mori (€5 truffle polenta bites).

2:00 PM: Hunt Murano glass in Dorsoduro’s backstreets. Pro tip: Ask for “sconto per amici di Nadia” (Nadia’s friend discount).

5:00 PM: Book a last-minute B&B on Giudecca via HotelTonight (€70/night).

8:00 PM: Aperitivo at Skyline Rooftop Bar (€10 spritz + sunset views).

How to Steal This Hack (Without the AI Meltdowns)

1) AI Tools: Use ChatGPT or Curiosio with these prompts:

• “Plan a 3-day Italy trip avoiding crowds, prioritising boutique hotels under €150, and including 1 unique local experience per day.”
• “Find villages in Liguria with under 1,000 annual tourists and a family-owned osteria.”

2) Boutique Hacks: Email hotels directly for unadvertised deals. Example script:

• “Ciao! I’m obsessed with your property. Any discounts for a 3-night stay in September? Grazie mille!”
• Target shoulder season (April-May/Sept-Oct) for 30% off rates.

Budget Secrets: Temu Pocket Translator: This gadget negotiated my gondola ride from €80 to €40, decoded a handwritten menu in Triora, and even snagged me a free limoncello tasting (“Your nonna’s recipe is poetry!”).

Ready to see exactly how I outwitted tourist traps, charmed Italian nonnas, and slept in castles? Hop over to my YouTube channel, Nomadia where I’m dropping weekly guides to hidden beaches, secret villages, and the craziest travel hacks you’ve never heard of. Smash that subscribe button—your next adventure is one click away.

P.S. Follow my Instagram for sneaky city facts, limited-time deals, and captions packed with tips you’ll actually use.

Arrivederci, mainstream travel!

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This article was written with the help of ai.