I’ve traveled with a “follow-my-heart” style for decades—no rigid schedules, just a few ideas and the freedom to change my mind. I often shorten or skip cities depending on how I feel.

After catching COVID a week before my 2021 Chile trip, that flexibility became a survival strategy. I had to reschedule not just international flights, but a maze of domestic ones, plus star-gazing tours—none of which could be canceled. Add in food poisoning in Costa Rica and altitude sickness in Atacama, and yeah… pre-booking everything just doesn’t work for me.

Now, I book almost everything last minute—flights, hotels, even tours. It helps me travel lighter, mentally and emotionally. On my most recent trip, I added a new kind of travel buddy to match my spontaneous style: AI tools like ChatGPT and Google Gemini—mostly helpful, occasionally silly, but surprisingly good company.

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✅ What AI Was Great For

✈️ 1. Destination Summaries

When I already had a destination in mind, I used AI to quickly summarize it—town size, local vibe, pace of life, and what type of traveler it suits. It helped me decide if a place matched my mood—quiet vs. lively, local charm vs. touristy spots.

Originally, I had planned to visit the Baltic countries after seeing the tulip fields in Lisse, Netherlands. But when my travel dates shifted, I asked AI what was happening in Europe during that time. That’s when it reminded me about Euroflora—a flower festival in Genoa that I had heard of before, but hadn’t realized this was the year it was actually happening.

That changed everything.

I started asking AI:

• “What’s the cheapest European city to fly into from NYC?”
• “How do I connect Amsterdam and an Italian city?”
• “Are intra-European flights cheaper than trains?”

It turned out that flying into London was cheaper than Amsterdam for my new start date, so I adjusted my route—starting in London, then continuing to Amsterdam, and finally heading to Italy.

Gemini gave me some real-time airfare estimates, and I used Google Flights and Skyscanner to verify prices.

In the end, AI helped me rebuild my trip around a new schedule, rediscover a once-in-five-years event, and plan an efficient, multi-country route—without getting overwhelmed.

🧳 2. Choosing Where to Go Next

When I wasn’t sure where to move on or feel like shorten the certain city, I asked things like:

• “Where should I go after Genova before Florence?”
• “Give me quiet towns between A and B with good train connections.”

AI compared options, listed pros and cons, and even flagged transportation complications. That’s how I ended up choosing Lucca—a peaceful, walkable town that gave me the perfect break after bustling Genova. I enjoyed cycling like a local, too.

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🌍3. Cultural Details

AI helped me navigate subtle but important customs that vary from country to country—and can feel awkward if you get them wrong.

• Tipping: I used AI to check whether tipping was expected at restaurants, hotels, and taxis. In some places, it’s included in the bill; in others, a small cash tip is appreciated. Knowing the local norm helped me avoid over-tipping or unintentionally being rude.
• Bar Culture in Italy: AI also explained how having breakfast at the bar is a local thing—and you avoid the table charge by standing. Morning coffee culture has unspoken rules too: Cappuccino is for breakfast only, and macchiato is the go-to for later in the day if you want milk in your coffee without breaking etiquette.

These little cultural cues helped me blend in more comfortably and avoid feeling out of place.

🎁 Souvenir Search with a Smarter Strategy

AI came in especially handy while shopping. I wanted to bring home souvenirs that were truly local, unique, and not easily found in the U.S.—not just pretty packaging or mass-produced tourist items.

In Florence, I picked up a truffle jar, but when I looked closely at the label, I realized it was actually from Sorrento—not Tuscany. That’s when I turned to AI to double-check where authentic truffle products are typically sourced, and whether it was worth keeping or replacing.

I also used AI to find out if certain items were available back home. After all, there’s no point in hauling something across continents if I can just order it online later.

Some of my final picks included:

• Dried mushrooms – great for cooking and hard to find in this form in the U.S.
• A homemade truffle jar from a local winery – this one was truly regional.
• Chocolate brands not marketed in the U.S.
• Loose teas and beef extracts – everyday items in some countries, but rare and interesting gifts back home.

AI was useful for verifying origins, comparing prices, and spotting fake “artisanal” goods. Just snap a photo or search the brand name—it can tell you a lot more than the label.

🗺️ 4. Pairing with Google Maps

AI was great for sparking ideas—restaurants, cafés, local dishes, or attractions nearby—but I always double-checked the details using Google Maps. That’s where I confirmed walking distance, opening hours, and the actual vibe of the place.

When I was hungry, I didn’t just want to eat anywhere—I’d ask AI things like:

• “What’s a local specialty in this city that doesn’t include meat?”
• “Where can I eat something light and regional near my hotel?”

AI gave helpful suggestions tailored to my mood or dietary preference, and then Google Maps helped me see menus, read recent reviews, and compare options visually.

The same combo worked for tourist spots, too. I’d ask AI for lesser-known attractions nearby, then use Maps to build a relaxed route that fits my energy and timing for the day.

And for train rides—I even asked AI,

• “Which side of the train has the better view from Florence to Rome?”

Small question, big payoff. These little tips made solo travel smoother, richer, and more intentional.

✍️ 5. Writing Thoughtful Messages (Without the Stress)

In Milan, my one-day tour was overbooked by about 10 people—including me. The company told us to “just buy your own train ticket and catch up,” which was incredibly frustrating. Instead of reacting emotionally, I used ChatGPT to help me write a firm but respectful message—calm, clear, and stress-free.

I also used AI to draft reviews for hotels and restaurants, whether the experience was disappointing or genuinely kind. Let’s face it—we usually only leave reviews when we’re either really upset or deeply moved, and sometimes we feel guilty for not writing one when someone truly deserves it.

In Florence, I arrived at my hotel around 7 or 8 AM and asked if I could have breakfast. The manager kindly said yes—and even refused to take any payment or tip. I was touched, but also exhausted. AI helped me quickly write a sincere thank-you message I might’ve otherwise skipped.

Of course, I never just copy and paste. I always add something personal—a moment, a gesture, a feeling—because while AI helps shape the words, the human touch still matters most.

6. 🧠 General Troubleshooting—or Just a Travel Buddy to Think Out Loud With

AI can be surprisingly helpful when you just need to talk things through. You can even use voice input—sometimes speaking or typing out your thoughts is the best way to clarify your own ideas.

For example, I once booked a hotel at an unexpectedly low rate on Booking.com. It turned out to be a system error on the hotel’s side, and the situation became confusing. I talked it over with AI, explained what happened, and asked for suggestions. Even when the solution isn’t new, just articulating the situation out loud helps reinforce your decision—or uncover alternatives you hadn’t considered.

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❌ What AI Was Not So Good At

⏱️ 1. Scheduling (Too Ambitious!)

AI sometimes builds schedules that look efficient on screen—but fall apart in real life. It suggested visiting both Vatican Museums and St. Peter’s Basilica in one day, and I actually did it. But the plan didn’t take into account the long lines or the fact that the Pope had recently passed, which made crowds and access unpredictable.

AI tends to miss real-time events, closures, or delays, and assumes everything runs smoothly. It also suggested doing things like traveling through three cities in one day with luggage, which might sound efficient, but just isn’t realistic.

I learned to treat AI’s itinerary suggestions as a starting point, then edit them based on actual conditions, energy levels, and what’s humanly doable.

🚉 2. Misunderstanding Time and Transit

AI doesn’t always understand how important it is to use time intentionally. For example, taking a train through Tuscany is much better before sunset, when you can actually enjoy the scenery. In other cases, I prefer to travel at night so I can wake up in a new city and make the most of the full day.

Maybe that’s a personal preference, but the tight, generic itineraries AI suggested didn’t work for me. I needed to create my own—choosing when to move, when to pause, or whether to stop in a small town along the way.

AI was a helpful starting point, but in the end, only I know what pace and timing feel right for my trip.

📅 3. Outdated Info

It recommended transport passes that weren’t needed. For example, during Euroflora, public transport was free in Genoa, but AI still told me to buy a pass. Some info, like the Rome Pass, was also outdated.

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🧠 Keep in Mind…

• ChatGPT and Gemini often give different answers, so I usually ask both and compare. It’s like getting two second opinions.
• Use AI for inspiration and decision support—not as your full-time travel planner. It’s great for brainstorming, but you’re still the one living the trip.
• Always cross-check anything involving timing, pricing, and availability. AI can’t see live data like sold-out trains, temporary closures, or special events.
• Personalize everything. AI gives generic suggestions by default, so always adjust based on your mood, energy, and travel style.
• Use your gut. AI doesn’t know when you’re tired, curious, overstimulated, or just need a gelato break. Trust your intuition as much as your itinerary.

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💬 A Few Real Questions I Asked AI

• A Few Real Questions I Asked AI
• “Can I get a VAT refund for this purchase in Italy?”
• “What’s the best way to visit 3 cities in one day—with luggage and no car?”
• “I have 3 extra hours in Rome before my flight—what can I do nearby using Tram 2 from my hotel?”
• “What’s the real historical background of the Colosseum?”
  (Because honestly, flipping through my digital guidebook felt like too much in that moment!)

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🎒 Final Thought: AI Is a Good Friend… Just a Little Silly

AI isn’t perfect—it’s like that silly, enthusiastic friend who’s full of ideas but doesn’t always think things through. You still have to double-check the details.

That said, it saved me time, helped me communicate politely, offered cultural insight, and kept my spontaneous trip running smoothly.

Just don’t let it plan your entire day from start to finish—and you’ll have yourself a surprisingly helpful (and slightly silly) travel companion. 😊

Related: Assess Your Capability: A Guide for First-Time Solo Travelers

Related: How to Choose the Ideal Travel Companion: A Comprehensive Guide