Lessons Learned from Letting AI Plan My Trip to Slovenia

Note: You’ll see me tossing around AI tools like Copilot, DeepSeek, and Perplexity. If you’re new to Generative AI, think of them as ChatGPT’s cousins – from other families.

Dear Invisible Friends,

This is not your typical cookie-cutter blog post. It’s not SEO-optimized or ready to take over the internet. Nope, this is more like a plate of slightly burned cookies fresh from the oven! It’s my raw, unfiltered narrative. I dare you to let it sink in and set off a little spark of inspiration. Or perhaps it will evoke at least a bemused chuckle. So, grab your helmet and buckle up; it’s going to be a wild ride!

Do you know that moment? You’re staring at the calendar. The urge to run away is biting at your heels. That’s me every summer. But this year, I let artificial intelligence help plan my escape. Yes, it’s the same breed of tech that keeps recommending me the exact laptop I bought last week.

Last year, I used Copilot to plan my trip to Sicily. This year, I experimented more. I recorded the successes and mishaps on my blog. I became a (slightly) tanned human Guinea Pig with countless photos.

Ever wondered if AI can really plan the perfect getaway? Get ready for the ultimate survival guide, packed with 7 DO’s and 7 DON’Ts for planning my trip with AI! Let’s be honest. Who wouldn’t want their robot sidekick to accidentally book them a tent in a cactus patch? It’s all for their Summer Adventure!

✅ DO’s

💭 DO: Whisper Your Wildest Dreams – Then Let AI Shout Options

I wanted Europe, but didn’t know where. My wish list? Sleep in, some intrigue, one story, and an uncrowded, relaxing yet adventurous escape.

I summoned DeepSeek and Copilot. I threw in my wildest cravings. I held my breath for algorithmic magic. Otherwise, I anticipated a digital facepalm.

Copilot spat back “Transylvania road trip.” (Who knew the robots had a goth phase?)

Meanwhile, DeepSeek enticed us to visit Slovenia. I’d previously only encountered it in WatchMojo videos about underrated travel destinations during the pandemic. Unfortunately, my friends, that ship has sailed. I quickly realized I wasn’t the only one who’d had the idea to visit Slovenia. There are many excellent reasons for this, Slovenia is a truly wonderful country!

Suddenly, I wasn’t boxed in by my own half-baked ideas. Turns out, sometimes the best muse is one that doesn’t sleep and has questionable taste in laptops.

🗺️ DO: Start With a Clear Plan – Then Keep Improving It

Once we chose Slovenia, it was time to shift from dreaming to planning. We needed to decide where to go. We had to blend relaxation and adventure. AI gave us detailed plans, sometimes too detailed, with constant hotel changes that seemed tiring. So we simplified, focused on a few regions, and embraced a slower pace. Each review helped us tweak the itinerary, resulting in a trip tailored to us.

We started in the Julian Alps, continued to the Adriatic Coast, and finished in the capital, Ljubljana. For the first two destinations, we had a rental car, which we returned before heading to Ljubljana.

Even the smartest itinerary can’t replace spontaneity, or a good pastry.

• Always double‑check: Copilot once booked us into “car camping” by accident.

🎒 DO: Let AI Simplify Pre‑Trip Logistics

I made a packing list with AI by sharing my trip length and activities. The Blue Whale (DeepSeek) advised smart-casual attire for dining in Slovenia. The AI also recommended a quick-drying towel and a light scarf or shawl for hikes, church visits, or cool evenings.

I also took some time to check out the upcoming local holidays and festivals. Thanks to the helpful Blue Whale, I found out August 15th is a holiday! 

Now for a classic “Dina moment”: I figured out (thanks to the Blue Whale) that the local currency and saved the emergency contact number for the area (turns out it’s the Euro and 112. Who knew? (Not me!)). 

On the practical side, the Blue Whale recommended I try learning Slovenian using the Mem Rise app, since Slovenian is not on Duolingo. I thought that was such a clever tip! Slovenians often speak English, German, or Italian. But tossing in a few Slovenian words? Instant sparkle. A dash of “Emily in Paris” energy, only with better pastries. It changed the vibe completely.

Note: This post was written prior to the tragic passing of Diego Borella, assistant director of Emily in Paris season 5.

• DeepSeek flagged a national holiday I would’ve missed. Saved me from closed‑everything chaos.

👋 DO: Talk to Locals

When we arrived at our first hotel, we had a pleasant conversation with the hotel owner. It was a long chat just before heading to Lake Bled. His advice was clear: “Don’t buy anything there.” He even suggested a cheaper place to park! He also advised us to skip Bled Castle. He recommended Ljubljana Castle instead. Later on, my husband overheard another tourist at Ljubljana Castle saying, “It’s much better than Bled Castle”.

On top of that, he thoughtfully made (and even printed, how old school!) a list of tourist destinations for our upcoming days. The best part? When both Human and AI come up with the same suggestion: skip the second waterfall at Slap Martuljek.

We visited the Ljubljana Tourist Information Center (TIC). We wanted to ask about purchasing tickets for both the castle and the cable car. Their guidance was much clearer. It was less confusing than the information I found on the GetYourGuide app. The price was the same.

📱 DO: Use AI as Your Pocket Guide + Translator

The first time I used AI as a guide (during this trip) was on Lake Bled. I was curious about a place. I took a picture and uploaded it to ChatGPT. I asked what it was and requested a short explanation. It happens to be Vila Bled.

I tried out ChatGPT’s voice mode while I was in Kropa. The voice sounded so friendly and human that it actually freaked me out! I didn’t chat for long. However, I enjoyed learning some interesting facts about the town’s fascinating history in metal forging.

In the end, I settled on using Perplexity AI as my assistant on Android. It provided concise answers. Although it gave a hallucinated response once, I received the correct explanation after some further prompting.

I had a funny experience at Izola during lunch. I thought, thanks to ChatGPT, that a page in a menu was all about sandwiches. However, when I asked the waiter, it was actually all about grilled dishes! I asked the waiter for help and ended up ordering ćevapčići – and wow, they were delicious! The waiter and I shared a laugh and agreed: ćevapčići are definitely better than sandwiches.

🌤️ DO: Use AI for Hidden Spots & Heatwave Hacks

Here’s today’s trick: I’m in Ljubljana, quickly realizing the city’s local-to-tourist ratio is, well, tragic. When the selfie stick density broke me, I asked every bot at my disposal: “Where do locals go to escape?” A fresh slate of under-the-radar places landed in my chat. If any of them live up to the hype, escaping crowds via AI is going on the permanent list. Test in progress.

We managed to avoid looking like a sun-dried tomato. This happened after a few days of sightseeing during a heatwave. We found some great tips for gliding through the shadows. I mean, you can navigate the streets of Slovenia’s capital like a Nosferatu. Well, more like a pro. Maybe I’m just embracing a bit of a Goth Phase myself!

Time travel before arriving at the capital. We needed to return our rental car at Ljubljana Airport by 5:00 PM. We checked out of our hotel in Fiesa on the Adriatic Coast. We planned to visit the charming coastal town of Koper, but concerned about summer traffic, I used GPT-5 via the sider.ai app to check typical jams. This helped us factor in extra travel time, and we left Koper accordingly, arriving an hour early!

🧭 DO: Trust Your Intuition

Everyone has their preferences or even limitations. Nobody knows better than you what you like best or what you can’t do. In my case, I’ve heard fireworks in my mind when I’ve read about the Pharmacy and Alchemy museum Radovljica, Salt Pans at Sečovlje Salina Nature Park, and specialty coffee in Ljubjlana, that was my reason to visit Pritličje two days in a row and order the same (delicious) cold brew lavender coffee.

Human Judgment > any algorithm

You made it this far? Grab a snack and keep scrolling for the Don’ts and epic blunders!

Here you have some AI-generated snacks I encountered during my trip to Slovenia.

🚫 DON’Ts

🚗 DON’T: Blindly Obey

The app’s genius? Suggesting my husband and I sleep in our rental car. Thanks, AI. Maybe next time I’ll just ask my mom.

💸 DON’T: Fall for Luxury Bait

AI threw a €1,000-a-night “storybook village hotel” my way. Did I book it? Unless my last name becomes Rockefeller, that’s a big, digital NO. Double-check, reality-test, and book like a pragmatist.

🍺 DON’T: Let AI Plan Bad Combos

Case in point: AI’s suggestion to drive to a beer fountain. Fun, until you realize beer and steering wheels should not mix. We embraced public transit and left the reckless ideas to the bots. In the end we didn’t go, but if we were, it would have been on public transport.

🖼️ DON’T: Chase Hallucinations

We had some funny disappointments (best to just let go). A Dance Macabre fresco in another city! A “Beekeepers’ Plate” that wasn’t on the menu, but the food and view were still great. One restaurant tipped to us was over 80 km away! Even GPT-5 can make mistakes.

⏳ DON’T: Swallow Fantasy Schedules

One word: impossible. AI’s confident I can drift through two museums in separate towns before closing time, when in reality I’m racing the clock just to finish lunch. I chose just one. Also, the heartless robot suggested staying only 50 minutes at the salt pans, rude.

💬 DON’T: Skip Real‑World Advice

Local advice isn’t always the same as AI’s. Online platforms like Reddit and Facebook groups offer real-world tips. I’ve found out about cash/card use in Slovenia on a Facebook group and airport transfers on Reddit. Even when AI isn’t wrong, I still prefer advice from real people, even online.

🤖 DON’T: Make It All About AI

It’s tempting to dive into the rabbit hole. GPT-5 made its debut while I was trying to enjoy my holiday. But unless your travel buddy is Sam Altman himself, do yourself a favor and resist the urge! The whole point of taking a break is to escape the daily grind, not turbocharge it into overdrive. I even met a friendly couple at the Ljubljana Castle cable car line who planned their entire trip with ChatGPT. I must admit, I fanned-girl’d a bit.

🏁 Conclusion

AI is that over‑excited tourist who swears every alley is a shortcut – straight to a mime convention. Let it add new tunes to your travel playlist, but keep your internal compass (and taste for chaos) ready.

Best case: jaw‑dropping stories.
Worst case: a viral punchline at family dinner.

With a dash of AI and a sprinkle of common sense, your holiday is set for adventure! Have a blast plotting your next misadventure with AI, and if it goes off the rails, you can blame the robots!

How Would You Use AI to Plan Your Adventure? Share Your Funniest AI Travel Moment in the comments below.

RoxenOut!

How did I do it? / References:

🤖 Toolbox Talk: I used Sider AI’s AI writer and ChatGPT-5 in Copilot to help clarify my ideas and structure my initial draft, which was a voice recording transcribed with Otter AI. The personal stories, final verdict, and all the laughs (or cries) are 100% human-generated. I believe in using AI as a co-pilot, not an autopilot.

LinkedIn Post (In Dutch) about Planning your holidays with AI.

I used Prompt Maker GPT by Ruben Hassid to refine my travel prompt (both for Europe and then for Slovenia). Next, I ran that improved prompt through both DeepSeek and Copilot. I answered each AI’s follow-up questions as specifically as I could. This wasn’t a one-and-done process: I iterated (yes, that means tweaking and re-running prompts) until the suggestions started making sense.

Prompt Maker GPT By Ruben Hassid.