By James Buckley Thorp, an experienced entrepreneur and founder of a new AI Stealth Startup.
Holiday planning should feel exciting. Instead, it often feels like work. Endless adverts, retargeted deals, and comparison sites all compete for attention, making it harder to decide, not easier. Increasingly, people are turning to AI not to replace travel agents, but to cut through the noise and regain clarity.
Used well, AI does not sell. It listens, analyses, and suggests. That difference matters.
Stop scrolling. Start briefing.
The most effective way to use AI for travel planning is to treat it like a professional planner, not a search engine. Generic questions lead to generic answers. Specific briefs lead to useful results.
Start by outlining what actually matters to you: budget, length of stay, preferred departure airport, hotel standard, pace of the trip, and the overall vibe. Relaxed or energetic. Cultural or coastal. Familiar or new. AI works best when you are honest, not aspirational.
When choice becomes noise, let AI think
My husband and I both love Greece and Italy, but when planning our last trip we felt paralysed by options. Every destination looked perfect. Every hotel claimed to be “ideal”. The more we searched, the less confident we felt.
Instead of browsing, we uploaded everything we wanted into ChatGPT: the countries we liked, the star rating of hotels, how long we wanted to go for, which airport we preferred to fly from, and what we wanted from the hotel itself. We asked it to go into deep research mode so it could properly think, not just reply.
Two strong answers beat twenty weak ones
Rather than returning dozens of options, the AI narrowed our choices to two destinations that genuinely fit our brief: Puglia in Italy and Crete in Greece. It explained why each worked, what the trade-offs were, and where each destination excelled.
We chose Crete. We knew Greece well, but had never been to Crete, which made it feel both safe and new.
Choosing the right hotel, not just a hotel
AI then suggested two hotel options that precisely matched our criteria. One stood out immediately. It was close to the airport, had a private beach, a gated resort layout, multiple restaurants, and the calm, high-quality atmosphere we wanted.
Crucially, the decision felt intentional. We were not reacting to discounts or glossy photography. We were choosing something aligned with a clear brief.
We booked it, and it became one of the best holidays we have ever taken.
Why this works better than booking sites
AI removes emotional clutter. It does not push urgency, upsell upgrades, or reward endless browsing. By structuring preferences first and analysing options neutrally, it reduces both impulse decisions and booking fatigue.
Five practical ways to use AI for your next trip
- Be specific about what you want and what you do not.
- Include logistics like flight time, transfer length, and airport preference.
- Ask for two or three options, not ten.
- Let AI research before responding where possible.
- Always sense-check prices, reviews, and policies before booking.
Planning without pressure
AI is changing holiday planning by making it calmer and more deliberate. It does not remove the joy of choosing where to go. It removes the noise that stops you enjoying the choice.
About the expert
James Buckley Thorp, who featured on Channel 4’s The Inheritance, is the founder of a new AI Stealth Startup and co-host for Posh and Specs Podcast. He an entrepreneur with over 15 years of experience building and scaling ventures across retail, insurance and technology.
