As of 13 August 2026, AI can plan a trip with multiple destinations.

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 a free AI chat tool and gather your departure point, destinations, dates, traveller details, budget, transport preferences, pace and accessibility requirements.
   2. Paste the prompt with your trip details filled into the bracketed slots, then save the proposed order of destinations and the day-by-day itinerary.
   3. Ask the tool to revise the route if any journey is too long, a connection is tight, or the plan exceeds your budget or preferred pace.
   4. Open the linked official sources for each transport leg, attraction and entry requirement, then compare their current dates, times, rules, prices and availability with the draft.
   5. Check UK entry and travel guidance on GOV.UK for every destination and resolve any passport, visa, insurance or transit requirement before booking.
   6. Check accommodation and transport directly with the named providers, then replace every CHECK LIVE item with a confirmed detail or remove it.
   7. Book the route in an order that protects essential connections, save each confirmation and update the itinerary with booking references, cancellation terms and realistic transfer buffers.

   Prompt

   Plan a multi-destination trip using the information below.
   
   Trip details:
   - Starting point: [UK departure town or airport]
   - Destinations, in any required order: [list]
   - Travel dates or number of nights: [details]
   - Travellers: [number and ages, if relevant]
   - Total budget: [amount and currency]
   - Preferred transport: [rail, flights, driving, ferry or no preference]
   - Accommodation preference: [details]
   - Pace: [slow, moderate or fast]
   - Must-see places or activities: [list]
   - Things to avoid: [list]
   - Food, mobility, health or accessibility requirements: [details]
   - Passport or nationality information relevant to entry rules: [details, without full passport numbers]
   
   Create a day-by-day itinerary in a table. Optimise the order of destinations and explain any major trade-offs between cost, travel time and convenience. For each travel leg, give the likely transport mode, departure and arrival locations, approximate journey duration, connection risks and a sensible buffer. Suggest areas to stay and activities that fit the stated pace and budget.
   
   Do not invent live prices, availability, opening times, transport schedules, visa rules or entry requirements. Mark anything that needs checking as CHECK LIVE. Cite or link the official source for each important transport, entry, safety, attraction or booking claim. Separate confirmed facts from suggestions. End with a booking checklist in the correct order and list every assumption or missing detail that could change the plan.

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