AI prompt for planning a travel itinerary

Written for Claude. Compiled as a planning / strategy task — turning a goal into an ordered, actionable sequence of steps.

<role>
You are an experienced strategist who plans backwards from the outcome.
</role>

<context>
Travelling: {{travellers}}. Budget: {{budget}}. Getting around: {{transport}}. Time of year: {{when}}. What we care about: {{interests}}.
</context>

<task>
Plan a {{duration}} itinerary for {{destination}}.
</task>

<approach>
Work through the problem step by step before giving your answer. Show the reasoning that actually drives your conclusion rather than a tidy summary written after the fact.
</approach>

<constraints>
- Every leg must be reachable by the stated transport. Do not assume a car.
- Give rough daily costs.
- Do not schedule more than one major activity per day plus travel.
- Flag anything that needs booking in advance.
- Say what to do if the weather is bad.
- Order steps by dependency, not by importance. A step must never require the output of a later step.
- For each step, state the concrete output it produces and how someone would know it is finished.
- Name the assumptions the plan rests on, and what would have to change for the plan to fail.
</constraints>

<output_format>
Respond in Markdown. Use descriptive headings, and keep paragraphs to three sentences or fewer.
</output_format>

<success_criteria>
Before you finish, check the output against every item below and fix anything that fails.

- Someone could follow this without a car if that is what was stated.
</success_criteria>

Now, plan a {{duration}} itinerary for {{destination}}.

Open this in the prompt builder to add your own context and see what would improve it most.

What makes planning a travel itinerary hard to prompt for

Generated itineraries pack in far more than a day holds and quietly assume a car. Opening hours and seasonal closures are also the sort of specific fact models get confidently wrong.

Why this prompt works

Background comes before the instruction

The model reads the situation before it learns what to do with it, which stops the instruction being diluted by everything that follows. The task is then restated as the final line, where models weight it most heavily.

Rules a planning / strategy task assumes but nobody writes down

Order steps by dependency, not by importance. A step must never require the output of a later step. For each step, state the concrete output it produces and how someone would know it is finished. These are added automatically because leaving them implicit is the most common reason this kind of output disappoints.

Success criteria the model checks itself against

Stating how the output will be judged gives the model something concrete to verify before it finishes. Prompts without criteria produce work that is plausible but incomplete, because nothing defined when it was done.

What to replace

Check the output before you use it

• Verify opening hours and seasonal closures independently — these are frequently wrong.
• Check every transfer is actually possible with your stated transport.
• Count activities per day. More than two plus travel is a schedule nobody keeps.

The same prompt for other models

Identical content, packaged the way each model reads most reliably.

## Role

You are an experienced strategist who plans backwards from the outcome.

## Context

Travelling: {{travellers}}. Budget: {{budget}}. Getting around: {{transport}}. Time of year: {{when}}. What we care about: {{interests}}.

## Task

Plan a {{duration}} itinerary for {{destination}}.

## Approach

Work through the problem step by step before giving your answer. Show the reasoning that actually drives your conclusion rather than a tidy summary written after the fact.

## Constraints

- Every leg must be reachable by the stated transport. Do not assume a car.
- Give rough daily costs.
- Do not schedule more than one major activity per day plus travel.
- Flag anything that needs booking in advance.
- Say what to do if the weather is bad.
- Order steps by dependency, not by importance. A step must never require the output of a later step.
- For each step, state the concrete output it produces and how someone would know it is finished.
- Name the assumptions the plan rests on, and what would have to change for the plan to fail.

## Output format

Respond in Markdown. Use descriptive headings, and keep paragraphs to three sentences or fewer.

## Success criteria

Before you finish, check the output against every item below and fix anything that fails.

- Someone could follow this without a car if that is what was stated.

Now, plan a {{duration}} itinerary for {{destination}}.

**Task**

Plan a {{duration}} itinerary for {{destination}}.

**Role**

You are an experienced strategist who plans backwards from the outcome.

**Context**

Travelling: {{travellers}}. Budget: {{budget}}. Getting around: {{transport}}. Time of year: {{when}}. What we care about: {{interests}}.

**Approach**

Work through the problem step by step before giving your answer. Show the reasoning that actually drives your conclusion rather than a tidy summary written after the fact.

**Constraints**

- Every leg must be reachable by the stated transport. Do not assume a car.
- Give rough daily costs.
- Do not schedule more than one major activity per day plus travel.
- Flag anything that needs booking in advance.
- Say what to do if the weather is bad.
- Order steps by dependency, not by importance. A step must never require the output of a later step.
- For each step, state the concrete output it produces and how someone would know it is finished.
- Name the assumptions the plan rests on, and what would have to change for the plan to fail.

**Output format**

Respond in Markdown. Use descriptive headings, and keep paragraphs to three sentences or fewer.

**Success criteria**

Before you finish, check the output against every item below and fix anything that fails.

- Someone could follow this without a car if that is what was stated.

Now, plan a {{duration}} itinerary for {{destination}}.