AI-Powered Tour Matching for the #1 Tour Guide Company in Flanders

The bigger picture

Legends Tours organizes guided city walks in Bruges, Ghent, Antwerp, and Brussels. Their tours are all about local storytelling, authenticity, and connection.
Every guide has their own story to tell, and every city reveals a different side of Belgium.

Direct bookings for Legends through the website were already strong. The real challenge was not to get more visitors, but to get them to choose private tours instead of free ones.
Free tours attract a wide audience, but private tours generate more value for both the guide and the company.

Legends wanted a simple, human way to help visitors discover which experience fits them best. A guided flow that naturally highlights the value of private tours without feeling like a sales push.

What we delivered

A simple way to make the right choice as easy as possible.

We built a guided selling tool that helps every visitor find their ideal city tour.
It asks a few simple questions, understands what they’re looking for, and instantly recommends the best match - complete with a personalized itinerary and email follow-up.

Behind that smooth experience is an AI-driven workflow that filters over 100 tours, balances free and private options, and learns from every interaction.

For Legends Tours, it means less noise, more relevance, and a booking experience that feels effortless from start to finish.

Why this matters

Most travelers don't realize how different a private tour is from a free one.
Private tours offer flexibility, exclusivity, and deeper storytelling, but those advantages easily get lost in a long list of tour options.

By turning the decision process into a guided conversation, Legends helps visitors reach their ideal match faster.
The new configurator asks a few questions, learns what people value most, and instantly recommends a tour that fits.

Built with n8n, OpenAI, Fillout and Loops, the configurator combines automation, AI reasoning, and structured data to deliver personalized tour suggestions.
Hosted on a self-managed Hetzner stack with Docker and Caddy, it’s fast, multilingual, and fully scalable for future features.

It feels like a friendly local giving advice - not an algorithm trying to sell.

The result is clear: less confusion, more clarity, and a growing share of private tour bookings.

Under the hood

Behind the scenes, the configurator runs on a custom-built AI workflow in n8n.
Each user input is sent through a prompt engine that crafts a context-aware request for the AI agent. The agent then matches preferences with the right tours using a structured output parser and real-time data retrieval.

From there, the flow compiles a personalized itinerary and automatically triggers a transactional email with the proposal.

Automation flow - built in N8N
It’s a seamless mix of prompt engineering, automation, and smart data handling – built for scalability, reliability, and multilingual logic.

Tech stack

Hey, you know us. We're quite the creative nerds. In the 2% chance you'd be interested in the tools we used, here's the breakdown.

The essentials

  • n8n - workflow automation and orchestration
  • Loops.so - transactional email delivery and personalized dynamic templates
  • Fillout form integration - captures user preferences in a conversational way
  • OpenAI (GPT model) - AI reasoning and personalized tour matching
  • Hetzner Cloud + Docker + Caddy - secure and self-hosted infrastructure

And if we're getting real deep?

  • Structured Output Parser - ensures reliable and structured AI responses
  • Custom “get_tours” tool - retrieves and filters data from the JSON tour database
  • JavaScript code nodes - handle filtering logic, language mapping, and payload transformations
  • JSON-based tour database - 100+ tours structured by type, city, and availability
  • Webhook endpoints - manage form submissions and AI responses
  • Itinerary page generator - dynamically builds personalized tour overviews
  • Redis cache layer - for stability and optimized workflow performance

Breakdown of the service

  • Strategy and concept - Together with Legends, we mapped the key decision points: city, type of activity, and personal preferences such as “food tasting,” “historical,” or “alternative.”
  • AI recommendation system - A GPT-powered agent built in n8n analyses more than 100 tours and selects the most relevant matches, prioritizing private tours where it makes sense.
  • Technical architecture - A JSON-based tour database with multilingual logic (EN, NL, ES) and dynamic email generation.
  • UX and flow - A conversational question flow that feels intuitive and ends with an instant recommendation page and follow-up email.
  • Automation layer - Transactional emails handled via Loops, with fallback logic and modular setup for easy expansion.
  • Scalability - Built to grow into a full guided selling platform that can later include transport, accommodation, and upsells.

What our client walked away with

A configurator that doesn’t just ask questions - it helps people make the right choice for their preferences.

For Legends Tours, this means:

  • More private tour bookings without losing traction from free tours.
  • Better insights into what visitors want across cities and themes.
  • A smoother user experience that turns curiosity into bookings.
  • A scalable system ready for future growth.

Each interaction with the configurator becomes a small feedback loop, helping Legends understand travelers better and refine their offer season after season.

🔗 See the configurator live
https://explore.legendstours.be/start

Or discover how an AI-driven recommendation system can guide your visitors toward the experiences that matter most.
👉 Talk to Kaffie