“Don’t be afraid to screw up — just start.”

That line from Lee Nettles, Executive Director of the Outer Banks Visitors Bureau, stuck with me long after our first Mindtrip webinar wrapped. 

We recently brought together leaders from Discover Puerto Rico, the Outer Banks Visitors Bureau and MMGY Global (representing Visit Costa Rica) to talk about how top DMOs are using AI on their websites — and what it really takes to get it right.

The conversation was honest, energizing and full of practical insight. And Lee’s words summed up exactly where many destination marketers are with AI right now: curious, cautious and wondering if it’s still too early.

But here’s the thing — it’s not. AI isn’t some distant innovation. It’s already changing how travelers discover, plan and book trips. And the DMOs leaning in are seeing results.

The need is clear. There’s endless inspiration at the top of the funnel — TikToks, Instagram posts, travel blogs. And there’s no shortage of booking options at the bottom. But in between — the moment when travelers want to turn interest into action? That’s where things fall apart.

AI is helping bridge that gap. Not just by answering questions, but by helping travelers say,

“I know exactly what I’m going to do once I get there.”

What Prompted DMOs to Make the Move?

During our webinar, I asked each panelist: what made you decide now was the right time to explore AI?

Lee shared that the push came from a mix of curiosity and urgency.

“I was reading all the articles and watching the demos,” he said. “There was this sense that something big was coming and I didn’t want to be behind it. I wanted to get ahead of it and understand what it could really do.”

For Delissa Zeda-Sánchez, Director of Digital Marketing at Discover Puerto Rico, the decision was both about innovation and practical need. She explained that their team had often heard the question from local partners:

“Why don’t you have a booking platform on Discover Puerto Rico?” AI gave them a way to close that loop — surfacing experiences and linking visitors directly to partner sites, without changing the core purpose of their website.

She added that they had evaluated several solutions before committing, noting,

“We wanted to ensure the platform would learn the voice of our brand and accept guardrails to keep responses in line with the messages we promote.”

Robert Patterson, SVP of Marketing Tech at MMGY Global, said timing was driven by maturity in the tools and a desire to do more than just test.

“What made Mindtrip stand out was that it wasn’t just a chat tool. It felt like a platform that could actually change the trip planning experience.”

He emphasized that traveler expectations have evolved:

“They don’t want to open 15 tabs. They want one smart assistant that just gets it.”

More Than Just a Chatbot

A key theme across the board: AI works best when it’s treated as a core part of the user experience — not just a floating help icon in the corner.

Most legacy chatbots operate like FAQ engines. They return pre-written answers to keyword-based queries and often lack real utility. What we're seeing now is something fundamentally different: interactive trip planning, powered by AI. Instead of canned responses, users receive rich, dynamic answers — complete with place details, interactive maps, photos, user reviews and links to book or save activities.

Just as important: travelers can ask anything. Whether it’s “What’s the best neighborhood for families?” or “Where can I find vegetarian-friendly restaurants near our hotel?,” they’re getting personalized, real-time responses based on a combination of public data and DMO-curated content.

This is possible because today’s AI solutions are layered on top of large language models (LLMs) with three essential components: robust travel knowledgebases, DMO-sourced content and key facts that steer the conversation. These can include sustainability filters, region-specific promotions or a focus on highlighting locally owned businesses. The result is a guided experience that still feels personalized and open-ended.

Robert noted that how and where users engage with AI makes a big difference. “People said, ‘This AI is great, but there’s only one access point to get to it.’ So we looked at new ways to surface it — more entry points based on the page a user is on, and tailored prompts depending on what they’re reading.”

He also highlighted the value of deeper integrations: “The ability to bring in Google Maps, ratings and reviews made the site more sticky and gave users fewer reasons to click away.”

This shift — from static chat to interactive trip-building — moves the DMO website
from informational to experiential.

What the Data Is Telling Us

We’re still early in the journey, but the initial results are promising:

• 3x more engagement: Visit Costa Rica saw over 3% of all website sessions interacting with AI — triple the engagement of traditional chatbot tools.
  
  
• Longer, deeper conversations: On Visit Costa Rica, users typically exchange 4–5 messages per session, a sign of meaningful engagement.
  
  
• Fast traction: Discover Puerto Rico saw 700+ chat sessions and over 4,000 messages within just 20 days of launch.

Panelists are also beginning to track KPIs like:

• Clicks to partner sites
• Itinerary builds and saves
• Email and newsletter opt-ins

What the Conversations Reveal

AI is helping destinations connect with travelers in ways that are not only efficient, but deeply human.

Delissa noted how users ask thoughtful, specific questions — like

“I’m traveling with my grandparents and I want to do some easy hikes. Which ones do you recommend?”

These are the kinds of requests that often go unanswered by traditional navigation menus.

At the Outer Banks Visitors Bureau, those insights are already reshaping how they think about content strategy.

“It’s been helpful in developing new guides and content to scratch an itch we didn’t know was there,” Lee shared.

He also framed success through a simple lens:

“If I can help ease a customer’s journey to learn about my area and book a trip, then that’s good enough for me.”

Getting It Right

Of course, implementing AI comes with thoughtful concerns — tone, accuracy, brand safety and content control. Each of the panelists acknowledged early hesitation, but they also shared how those concerns were addressed through intentional collaboration and iteration.

Lee pointed out initial worries around geographic prioritization.

“At first, it wasn’t surfacing our region in the results the way we needed it to,” he said. “We had to work through that to make sure the content aligned with our destination goals.”

Robert added that brand safety was top of mind from the start.

“As an agency, we’re always thinking about voice, tone and whether the experience truly reflects the client’s brand. That was a big part of how we evaluated early options.”

Delissa emphasized the importance of hands-on effort. Her team evaluated multiple tools before selecting one that aligned with their content strategy and brand standards. Then they contributed thousands of key facts and editorial pages, and worked closely with us to test and fine-tune the model.

“It cannot learn if you don’t feed it,” she said. “But if you do the work, the results are absolutely worth it.”

Lee echoed the need for balance.

“While [the AI] is able to prioritize our data, you don’t want to be so rigid that you end up cutting out what makes AI great in the first place. If it’s just returning content from my website, it takes the fun out of it.”

The Road Ahead

AI isn’t a shiny new feature. It’s a shift in how people interact with information and how they expect to plan travel. And for DMOs, it’s not just about adopting the technology. It’s about redefining the role of your website as a true planning companion.

As Robert noted, it’s not about bolting AI onto your site — it’s about making it central to how your website serves travelers.

The DMOs embracing this shift aren’t just staying relevant. They’re helping define the next era of destination engagement.

If you're starting to explore how this could work for your organization, you're not alone — and you're right on time.