Travel planning has evolved far beyond flipping through guidebooks. Today, tools like ChatGPT can generate ideas, answer questions, and help organize travel details in seconds. For many travelers, it’s become a go-to resource for inspiration and logistics — but using it effectively takes a little know-how.
This guide walks you through how to get the most from ChatGPT for trip planning, the potential pitfalls to watch out for, and why it works best as a partner to — not a replacement for — human expertise.
What is ChatGPT and How Does it Work?
ChatGPT is an advanced AI tool designed to understand natural language prompts and respond conversationally.
You can ask it broad questions, such as “Where should I go in Europe in May?” or detailed instructions like “Create a 7-day itinerary in Portugal focused on food, wine, and coastal towns.”
The more detail you provide, the better the responses. Think of it as a highly capable research assistant — one that can brainstorm destinations, build sample itineraries, and suggest unique experiences — but still needs guidance and fact-checking.
Brainstorming Destinations
ChatGPT is especially good at helping narrow down options based on your interests and timeframe.
- Example prompt: “Suggest European cities for a 10-day trip in late spring with a focus on art museums and wine tasting.”
- Example prompt: “Recommend coastal European towns for a September trip with hiking trails and historical sites.”
If you need a head start on where to go, our Top European Destinations 2025 article offers plenty of curated ideas.
Building a Sample Itinerary
Once you know your destination, ChatGPT can map out your days based on trip length and priorities. You can ask it to:
- Arrange attractions geographically to reduce travel time.
- Balance sightseeing with rest days.
- Focus on themes like food, history, or outdoor adventures.
Example prompt: “Plan a 7-day itinerary in Scotland focusing on castles, whisky distilleries, and scenic drives.”
For trip timing considerations, see our guide to the
Best Time of Year to Visit Italy
.
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Finding Unique Local Experiences
ChatGPT can recommend activities tailored to your trip:
- Seasonal events (e.g., Christmas markets, summer festivals)
- Hands-on workshops or classes
- Lesser-known museums or walking tours
If you’re looking for destinations steeped in wellness and tradition, our Europe’s Historic Spas article is a great resource.
Getting Practical Travel Advice
ChatGPT can offer useful tips on:
- Transportation between cities
- Seasonal packing suggestions
- Basic language phrases
- Local customs and etiquette
Example prompt: “What should I pack for a late spring trip to Switzerland, including mountain hikes and city sightseeing?”
While AI is great for general guidance, always confirm details like train schedules or visa requirements.
For up-to-date information, see our guide on
Europe’s NEW Entry Requirement
.
Potential Problems to Keep in Mind
- Outdated information: AI answers aren’t always current.
- Generic suggestions: Recommendations may favor well-known spots over hidden gems.
- No booking capability: It can’t reserve hotels, tickets, or tours.
- Logistical gaps: May not account for travel time, local closures, or seasonal limitations.
- No personal insight: It can’t replace the perspective of someone who’s actually been there.
Why the Human Touch Still Matters
ChatGPT is an excellent research partner — but human expertise adds depth, accuracy, and personal insight that AI can’t provide. A travel professional can confirm availability, adapt to last-minute changes, and recommend experiences perfectly matched to your style and pace.
If you’d like to see what that expertise looks like in action, our guide on How to Choose the Best Travel Agent explains how to find the right match for your needs.
Hi, I’m Jack Baumann – founder of Guidester. I’ve spent over 15 years living and traveling throughout Europe, and I created Guidester in 2014 to help others experience the best of what Europe has to offer. What started as a passion project has grown into a full-service travel concierge and tour company, designed to make your journey smoother, richer, and more meaningful.
Want to know more about my story? Click here to learn more about me.
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Jack Baumann
President of Guidester
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