Welcome to a group of people who give a damn.
Smart Pineapple: Where Hospitality Meets AI (and Still Feels Human)
You are building something that matters.
Whether it’s a vacation rental, a boutique inn, or a local destination, your work creates connection, memory, and meaning for travelers.
At Smart Pineapple, we help you grow bookings and simplify marketing using AI tools and human-centered strategy designed for independent hospitality businesses and destination leaders who believe in the power of community-driven tourism.
Join readers in 34 states and 64 countries — a global community of hoteliers, vacation rental owners, and destination leaders who care as much as you do.
Why Smart Pineapple Exists
I started Smart Pineapple because too many incredible hosts, innkeepers, and small destinations were burning out, trying to keep up with marketing, technology, and AI tools built for global hotel chains.
That includes the small DMOs, tourism boards, and chambers doing more with less — trying to promote entire regions on limited budgets while supporting local businesses and keeping tourism authentic.
When I started my first business, I had to figure it out alone.
I built Smart Pineapple so you don’t have to.
You’ll get the kind of support and strategy I wish existed years ago.
This community exists for people like you — the ones who make guests feel at home, build local pride, and bring travel to life in ways no algorithm can.
Hospitality is not about clicks or commissions. It is about people.
That belief is at the heart of everything we teach and share here.
Who We Are
Founded by Kay Walten, a lifelong hospitality entrepreneur, Smart Pineapple is trusted by vacation rental owners, hoteliers, property managers, and destination marketers around the world.
We help independent hospitality businesses and small destinations grow direct bookings, strengthen guest relationships, and adopt technology that serves them. Not the other way around.
Our focus is helping small teams harness the power of AI to market smarter, tell stronger stories, and connect travelers to real people and places. Without losing the human touch that makes hospitality special.
Together, we’re redefining what small, independent, and human-driven hospitality can look like in the AI era.
What You’ll Find Here
For Hosts and Hoteliers
Learn how to attract more direct bookings, create memorable guest experiences, and grow your business with purpose.
→ Explore posts
Destination Marketing
Learn how to engage local partners, design campaigns that strengthen your economy, and tell stories that make travelers fall in love with your place.
→ Read more
AI Workflows That Save You Hours
Use simple prompts, templates, and strategies to create marketing, respond to reviews, and brainstorm guest experiences in minutes — not hours.
→ Browse workflows
Rave Reviews
See how others use Smart Pineapple strategies to boost results, improve guest relationships, and grow visibility.
→ Read stories
How We Use AI
Learn how hospitality professionals use AI every day to:
Write listings, blogs, and social posts in minutes
Personalize guest communication at scale
Simplify reputation management and reporting
Find new marketing ideas and local partnerships faster
Everything here is tested in the real world, designed to save you time and keep hospitality human.
AI doesn’t replace creativity. It removes the busywork so you can focus on strategy, storytelling, guest experience, and community building.
The Podcast: Seen. Booked. Sane.
Some lessons are best shared in conversation.
On Seen. Booked. Sane., I talk with property owners, hoteliers, and destination leaders about what’s changing, what’s working, and how to stay human in the middle of it all — including how real people use AI to save time and tell better stories.
🎧 Listen on Spotify, Apple Podcasts, or right here on Substack.
Where to Start
If you’re new, begin with a few reader favorites:
The Nitty Gritty of SEO – Practical visibility wins for your property or destination.
From Oh No to Five Stars – Turn negative reviews into repeat guests.
Social Media That Gets You Booked – Build trust through real stories, not ads.
2025: The AI Era for Hoteliers – What the next wave of hospitality technology means for you.
Why Subscribe
Most hospitality advice out there is made for big brands with big budgets.
Smart Pineapple is made for you — the owner, manager, or destination marketer wearing a dozen hats.
When you subscribe, you’ll get:
✅ Practical insights you can use immediately
✅ AI tools and workflows that save you time
✅ Real examples from people who understand hospitality from the inside
✅ A sense of community with others building businesses that matter
You’ll learn how to use AI to simplify your marketing, personalize your guest experience, and free up time for the parts of hospitality you actually love.
Every article and workflow is designed to help you show progress fast — whether you manage one property, a regional campaign, or an entire destination.
No hype. No jargon. Just honest, human-first hospitality made smarter by technology.
Join readers in 34 states and 64 countries learning to grow bookings without burnout.
💡 Your answer helps us tailor future AI workflows and examples for you.
Welcome
You’re not just subscribing to a newsletter you’re joining a movement that believes small hospitality still matters.
Grab a coffee, read a post, or listen to an episode, and see how AI can help you do what you do best: create experiences guests never forget.
When small operators thrive, communities thrive too.
That’s hospitality worth fighting for.
Be Seen. Be Booked. Be Sane.
Smart Pineapple: Hospitality Meets AI (and Still Feels Human).