Kay Walten and Ivan Ivanovic with the title “From Storytelling to Bookings – How Independent Hospitality Wins With AI” from AI Tourism Talks Episode 7

What I Learned From Kay Walten About Why Storytelling Beats Feature Lists in Hospitality

Most small hotels and rentals still lead with the same message:

Pool. Wi-Fi. Breakfast included.

That is information. It is not a reason to care.

In a recent AI Tourism Talks Live, I spoke with Kay Walten, founder of Smart Pineapple and one of the early online tourism pioneers in Mexico’s Riviera Maya.

We focused on one simple idea: If you want direct bookings and loyal guests, you must stop leading with features and start leading with stories.

Here is a recap of the most important points from the session.

Why Storytelling Beats Feature Lists in Hospitality

Traditional hospitality marketing looks like a brochure.

Room type. Amenities. Price.

But when guests talk about their stay, they talk about:

  • How the host made them feel welcome
  • A moment that surprised them
  • Why the place felt right for them

Stories answer questions like:

  • Who is this place really for
  • What will I feel if I stay here
  • Why should I trust this team with my time off

Features confirm the choice. Stories create the choice.

For small operators, this is good news.

You might not have the biggest spa or the most advanced app, but you do have real people, real guests, and real experiences.

That is your advantage.

How to Make Your Content More Story Led

Here are the most practical ideas Kay shared for small hotels, vacation rentals, and local brands.

1. Start with three real guest stories

Talk to three guests:

  • Someone who returned
  • Someone who chose you over a chain
  • Someone who recommended you to friends

Ask them a simple question: What made this place feel right for you?

Take one or two strong sentences from each answer.

These lines are more powerful than most marketing paragraphs.

2. Turn one story into your main message

On your homepage or main booking page:

  • Open with a short story about the guest you serve best
  • Then share the features and practical details
  • Use photos that support the story, not only empty room shots

This makes your property feel specific, not generic.

3. Talk like a person, not a brochure

Kay’s advice is clear: Write the way you speak.

That means:

  • Simple language
  • Short sentences
  • Real examples

If your copy sounds like a travel brochure from the 1990s, it will be forgotten.

If it sounds like a real person talking about a real place, guests will remember it.

Using AI Without Losing Your Voice

Kay works with hospitality brands that want to use AI but are afraid of losing their identity.

Her approach:

  • AI is a support tool
  • Hospitality is still a human job

She uses AI to help clients:

  • Capture how owners and teams actually speak
  • Turn guest stories and reviews into content ideas
  • Keep the same tone on the website, email, and social posts

AI is used for speed and consistency:

  • Faster first drafts
  • Easier repurposing
  • Fewer blank-page moments

But the source material is still human:

  • The story of the place
  • The people running it
  • The guests they serve

If the inputs are generic, AI will only scale generic.

If the inputs are real, AI helps you publish more of what already works.

A Simple Story Upgrade Checklist

Kay shared a simple set of actions any operator can take this week.

1. Review your key pages
Look at your homepage, main listing, and About page.

Ask: Do they read like a list of features, or like the start of a story?

2. Add one real guest quote
Include one short quote that explains why a guest felt your place was right for them.

3. Lead with a story, then support with facts
On each key page:

  • First, explain who this place is for and what it feels like
  • Then list features, services, and practical info

4. Reuse stories across channels

Take one strong story and use it for:

  • A short social post
  • A paragraph in your newsletter
  • A short section on your website

5. Use AI to keep going

Feed AI a few of your stories and your best lines.

Ask it to suggest variations in the same tone for web, email, and social.

In under an hour, you can shift your main content from feature lists to story-led messaging.

Free Resources From the Episode

➡️ Kay Walten

➝ 30-Minute Direct-Booking Playbook
➝ Personas to Profit (2025 Edition)

To access these, send Kay a DM on LinkedIn with the keyword “DirectBooking” or “Profit”.

Website
https://www.smartpineapple.ai/

Substack AI for Hospitality
https://www.aiforhospitality.info/

➡️ Ivan Ivanovic

➝ 100 AI Prompts for Travel Tech & Tourism Brands
https://ai-tourism-innovator.framer.website

➝ AI Tourism Innovator Weekly

My free Saturday digest with AI travel news, prompts, and case studies
https://ai-tourism-innovator.beehiiv.com

Watch the full 39-minute replay
https://www.youtube.com/watch?v=SCaIcQbwfZw

Final Thoughts

Big brands will always have larger budgets and more tools.

They can not copy:

  • Your story
  • Your relationship with guests
  • The feeling of staying at your place

That is where storytelling and AI work together:

  • Storytelling gives people a reason to care
  • AI helps you share that story clearly and often

You do not have to fix everything at once.

Pick one page. Add one real story.

Make it easier for future guests to see themselves there.

The brands that do this now will stay memorable in a market that is full of similar offers.