As of 13 August 2026, AI can optimise your holiday itinerary.

What to actually do

1. Hand it to a person

   The route this page recommends

   A person who owns the outcome does this end to end, worth it when the failure is dear.

2. Use a tool built for this

   Second choice

3. Do it yourself

   The distant third

   A chat interface, chat-fluent skill, and roughly 30 minutes until you can act on the result.

   How to actually do it

   1. Open your existing booking confirmations, transport details and maps, then gather the exact dates, times, addresses, cancellation terms and passenger constraints.
   2. Paste the gathered information into the prompt, replacing each bracketed slot and stating any preference that matters, such as a relaxed pace or avoiding early starts.
   3. Ask the chatbot to produce the day-by-day itinerary and to mark uncertain or changeable details as CHECK LIVE.
   4. Open the official websites for each attraction, transport operator, accommodation and booking platform, then compare their current opening hours, journey times, availability and cancellation terms with the draft.
   5. Replace any stale or uncertain detail in the itinerary with the live information, and ask the chatbot to re-sequence the days around those confirmed times.
   6. Check each transfer on a current map or transport service, add practical buffer for delays and walking, then make bookings yourself through the relevant official supplier or booking platform.
   7. Save the final itinerary with booking references, addresses, contact details and a fallback plan for each important transfer.

   Prompt

   Optimise my holiday itinerary using the information below. Do not invent prices, opening hours, transport times, availability or booking terms. If a detail is missing or may have changed, mark it as "CHECK LIVE" rather than guessing.
   
   Trip dates: [DATES]
   Starting point and return point: [LOCATIONS]
   Destinations and places I must visit: [PLACES]
   Existing bookings with exact times and addresses: [BOOKINGS]
   Transport available or preferred: [TRANSPORT]
   Budget: [BUDGET]
   Pace: [RELAXED, MODERATE OR FAST]
   Interests: [INTERESTS]
   Accessibility, dietary or other constraints: [CONSTRAINTS]
   Places or activities to avoid: [AVOID]
   
   Produce:
   1. A day-by-day itinerary in local time.
   2. A realistic order for each activity, with travel time between stops shown separately from activity time.
   3. A short reason for each major ordering decision.
   4. One slower alternative for any day that is too full.
   5. A list of every detail that needs live checking before I book or rely on it.
   6. A booking and checking order, prioritising anything with limited availability or strict cancellation terms.
   
   Keep enough buffer for delays, meals and finding the correct station, airport or entrance. Do not recommend a connection unless the stated times make it plausible. Separate confirmed information from assumptions and questions for me.

   Open it prefilled in ChatGPT or Claude, or copy it into Gemini, which takes no prefill link.