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Magazine-Quality Itineraries with AI

Workshop·8 min read

Most itinerary tools force you to choose between speed and brand identity, which is why so many advisors still build by hand. You don't have to choose anymore. With a properly set up AI workflow (a branded template, a slide map, labelled elements, a brand guide, and clear tool instructions) you can drop in a messy DMC brief, a rough idea, and some supplier images, and get a finished, on-brand itinerary back in minutes. The setup takes a bit of time upfront, but once it's done you get hours back on every trip without giving up the look that makes the work yours.

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Our brand is our baby. The look, the feel, the way our itineraries land in a client's inbox, it's all part of what we actually offer. It's why a lot of us still use the slow tools we've always used. At least the output looks like us.

The current generation of itinerary builders mostly trades speed for identity. You get something fast, but it doesn't look like your work. So we go back to the slow way, because the slow way protects the brand.

The question is whether you still have to choose. With AI sitting next to your existing template, you might not.

From a rough document to something stunning, in one click

"Why can we not do this today with how much hype there is about AI?", newsflash we can. With the right set up and tools, AI can do all of that dreaded grunt work for us.

You drop in whatever you have. A messy DMC brief, a rough idea you jotted down in Notes, a couple of past itineraries you want it to pull text from, a folder of supplier images you've been collecting. Out comes a finished, multi-day, on-brand itinerary in your template. Dates in the right places. Activities in the right boxes. Images in the right slots. Your fonts, your colors, your layout, untouched.

What the AI actually needs to pull this off

Similar to working with a VA, you might want to have your SOPs and templates ready. AI can surprise you when you let it create things on its own but it is exceptional when you taught the AI exactly what you are after. Therefore the five things you need to get the best results are:

  • A branded itinerary template: For consistency of your brand and style, don't let the AI generate a new itinerary from scratch every time. That is where mistakes happen and you don't start from 0 every time either.

None of these things are complicated to create, but it takes some time to set up. And don't worry you don't need to get it right in one go you can iterate on your prompts and skills until you reach consistency.

We had another workshop about getting reliable results with AI which you can check out here: Getting reliable results with AI

The different tools you can use, and how AI works with each one

PowerPoint / Google Slides

PowerPoint is more AI-friendly than people expect. PowerPoint files are structured in a way that AI can read and edit directly, every element, every font, every color, every position. Claude has its own PowerPoint skill that handles this well.

The price you pay is twofold. It uses a lot of tokens, because the AI is opening up your file, editing it, and putting it back together for every change. And PowerPoint itself isn't the easiest place to make something genuinely beautiful, especially for itineraries. Flexible for the AI, less generous to the human polishing afterwards.

Although direct editing with google slides is possible there is not a great integration for AI systems except Gemini. However you can easily upload the powerpoint as google slides.

Canva

Canva is where most advisors actually work and the templates are genuinely beautiful. For humans, this is the nicest tool but for AI not so much.

The AI can fill in text, replace images, reposition and restyle elements. However It cannot make a new slide or make a new element. You also can't let the AI automatically copy a template, you need to do this yourself and point the AI to the copy for editing.

Canva is explicitly restrictive about what outside AI tools, like Claude and chatGPT, can do in order to push you to enterprise plans and their own Canva AI. Unfortunately for us, their tools don't connect to our data and are far worse.

This means that we need to work around some of these complications. For example your template better have five-day trip slides even when you normally only book weekend trips of three days, in case of a 5 day trip because with the Canva connection AI can not create slide pages.

There's always a bit of human work left at the end, no matter how good the input is.

Pencil.dev

The newest tool which has become super popular for UI design. Everything in a Pencil design is a named, addressable piece, so the AI can talk about "the Day Title" by name and edit only that. It was built for AI to use, it's easy to edit as a human, it can generate images for you, and it's free right now, so you're not paying for the credit-heavy back-and-forth that PowerPoint needs.

The catch is that it's young. You can't reposition images yet, and you can't style individual words inside a paragraph. Both have workarounds. And your templates probably aren't in Pencil yet, which is a one-time setup cost.

Claude design

You can set up a design system inside Claude that holds your brand guidelines, and store every template you've ever made in a digital folder. The AI then generates slides against your system without you having to re-explain it every time.

The catch is editing. To tweak something by hand instead of pulling the AI slot machine again, you have to download the file as a PPTX, and the conversion isn't always clean. Hard to stay in control of the small details.

Still new, getting better fast.

What I'd actually pick

Depends on where you already work.

If your team already lives in PowerPoint and you care most about consistency with what you produce today, PowerPoint plus a good skill file gets you there. Pay the token cost.

If your template is already in Canva and you mostly want the AI to do the text fill, Canva is fine, as long as you go in knowing you'll do the last bit by hand.

If you're starting from scratch or willing to rebuild a template, Pencil.dev. It's the closest thing to a one-click experience today.

If Claude is already where you do most of your AI work, Claude design fits in naturally. You stay in one ecosystem, the design system sits next to your other skills, and the AI already knows about everything else you've set up.

What's in my skill file

A skill file is the bit that turns any of these tools from "sometimes works in a demo" to "works every time on real briefs". It's a long prompt the AI reads at the start of every task, with everything it needs to know about how I work. Mine is around two pages plus a few supporting files. A few examples, pulled straight from it.

The brand rules. The colors and fonts are pinned to specific values so the AI can't drift.

Color palette: teal (#035476) for panels, bars, and backgrounds, cream (#F2EEE6) for info slides. These are the only two background treatments in the template. Fonts: Questrial (titles/headings), Inter (body/details), Cormorant (special headings). On teal backgrounds all text is white (#FFFFFF). On cream backgrounds, headers are teal (#035476) and body text is dark gray (#333333).

The voice. The tone is named, with a before-and-after rewrite example so the AI can pattern-match on what good looks like.

Bluestone itineraries are written in a warm, personal tone, like a knowledgeable friend who has been to these places and is genuinely excited to share them with you. Source material often arrives in a stiff, third-person tourism-copy style ("Guests will be greeted by..."). Rewrite it to feel more direct and personal ("Your guide meets you at the dock..."). Never invent information. If the source doesn't describe what happens during a food tour, don't make up what you'll eat.

Edge cases. Each common gap has a concrete rule, and the missing-info protocol kicks in after the deck is built.

Identify any fields that seem critically missing (no property name for an accommodation that clearly should have one, dates that appear cut off, incomplete location names). Use AskUserQuestion to present all missing items at once. Frame it as: "The itinerary is ready. I noticed these details seem to be missing from the source, can you provide them?" Do NOT block deck creation waiting for answers. Build first, ask after.

It reads like a style guide for a new team member. Most of it is just how you already work, written down once.

Takeaways

Most of the work is in the setup. The five things above (template, slide map, labels, brand guide, tool instructions) are the same kind of onboarding you'd give a virtual assistant on their first day. Write them down once and the AI behaves consistently brief after brief.

You have a choice on the tool. You can stay where you already work, PowerPoint or Canva or whatever your team lives in, and put AI on top of it. Or you can make the bigger jump to something built for AI collaboration like Pencil or Claude design and trade more upfront investment for a much cleaner AI experience. Both work.

Once the setup is done, you drop in a DMC brief and get a four-minute itinerary back, in your brand, ready to send. That's hours of work back, every trip.

  • A Slide map of the template: We don't want the AI to figure out which template layout is used for what information. "Alternate between the two variants of day itinerary layouts to make the presentation feel dynamic". Make sure that the order and feel of the template is consistent.
  • Labels of each element in the slides: Similarly to the slide map, we don't want the AI to figure out every new chat session where the destination images go vs the room images. Explain to the AI before hand in a skill/prompt template how to work with your template and its content.
  • A brand guide line: Explain to AI what colors you use, the spacing, the fonts, the title and body text sizes, your brand identity, the target customer, your specific tone of voice, anything you can think of that is important to your brand. All of this information helps AI to make the changes to the template when edge cases come up.
  • Instructions about the tools your use: Whether you are working in Canva, powerpoint or something else, telling the AI what tools it needs to use and how to use them, drastically reduces the amount of figuring things out on the fly