Automate Your Way Out of Holiday Arguments
My girlfriend and I have fundamentally different approaches to travel planning. She creates detailed spreadsheets with hourly itineraries. I book a flight and figure out the rest when I land.
This philosophical divide led to many "discussions" about upcoming trips. After the third argument about whether we needed to plan our Germany vacation down to the minute, I had a thought: What if I could automate my way out of this problem?
Enter Just Wing It - an AI trip planner that generates complete vacation itineraries in minutes.
The Problem (Every Couple Has It)
Her perspective: "We need to know where we're eating dinner on Tuesday, what the backup plan is if it rains, and how much everything costs."
My perspective: "Let's just see what happens. Adventure!"
The reality: We'd spend more time arguing about planning than actually planning.
I'm a developer. When I see a recurring problem, I build a solution. Even if that solution is born from equal parts love and laziness.
The Solution: Just Wing It
The app asks five simple questions:
- Where to? (e.g., Paris, Tokyo, NYC)
- When? (dates and duration)
- How many people?
- What's your travel style? (relaxing, adventure, culture, nightlife)
- Where should we send your itinerary?
Hit submit, and in 2-3 minutes you get a complete day-by-day itinerary with:
- Attractions and activities
- Restaurant recommendations
- Estimated costs (per person and total)
- Google Reviews integration
- Weather considerations
- Local transportation tips
The Technical Stack
Frontend: Next.js with a clean, mobile-first interface Backend Logic: n8n workflow automation AI Engine: OpenAI for content generation Data Sources: Multiple APIs for reviews, pricing, and local information
The beauty is in the workflow automation. When someone submits the form, n8n triggers a complex sequence:
- Input Processing - Cleans and structures user data
- AI Trip Generation - Uses OpenAI to create base itinerary
- Data Enhancement - Pulls in pricing, reviews, weather
- Output Formatting - Structures everything into a clean, readable format
- Delivery - Sends the complete plan via email
The AI Agent Configuration
The core of Just Wing It is the Trip Planner AI agent. I spent considerable time crafting the prompt to generate practical, realistic itineraries rather than generic tourist traps.
Key prompt elements:
- Include local favorites, not just major attractions
- Consider travel time between locations
- Mix planned activities with downtime
- Account for meal timing and local eating patterns
- Provide backup options for weather issues
The agent processes the user input and generates structured JSON output that the workflow then enhances with real-world data.
What I Learned Building This
User behavior is predictable: 80% of requests are for major cities (Paris, Tokyo, New York, London). The remaining 20% are where things get interesting.
Pricing data is messy: Restaurant costs vary wildly by source. I ended up using multiple data points and showing ranges rather than specific prices.
People want options: The most requested feature has been alternative suggestions. "This looks great, but what if we prefer quieter restaurants?"
Mobile-first matters: 70% of users submit requests on mobile devices, usually while discussing travel plans with someone else.
The Relationship Test
Three months after launching, my girlfriend used Just Wing It to plan our Barcelona trip. She made minor edits to the AI-generated itinerary but kept 90% of the suggestions.
The verdict: "This is actually better than my spreadsheets. It found restaurants I never would have discovered."
Mission accomplished. We haven't argued about trip planning since.
Technical Challenges
Rate limiting: OpenAI's API has usage limits. I implemented queuing to handle peak demand without crashing.
Data accuracy: Restaurant information changes frequently. I built in multiple fallback data sources and error handling.
User experience: The 2-3 minute processing time required careful UX design. Users get real-time status updates and can close the browser - the itinerary comes via email.
Cost management: AI API calls add up. I optimized prompts to be efficient while maintaining quality output.
Current Stats (3 Months Post-Launch)
- 1,200+ itineraries generated
- Average processing time: 2.4 minutes
- User satisfaction: 4.2/5 (based on follow-up surveys)
- Most popular destinations: Paris (18%), Tokyo (12%), NYC (11%)
- Return usage: 35% of users plan a second trip
What's Next
Collaborative planning: Let couples edit itineraries together in real-time Budget optimization: Help users find the best value for their travel style Local insider tips: Partner with local guides for authentic recommendations Trip memory keeping: Photo sharing and travel journaling features
The Real Lesson
Building Just Wing It taught me something about product development: the best solutions often come from personal frustrations.
I wasn't trying to disrupt the travel industry or build the next unicorn startup. I just wanted to stop arguing with my girlfriend about vacation planning.
Sometimes the most practical applications of AI aren't revolutionary - they're solutions to everyday relationship dynamics that happen to scale to thousands of other couples with the same problem.
Try it yourself: justwing.ai
Whether you're a detailed planner or a wing-it traveler, the AI finds a middle ground that actually works. Plus, it might save your relationship from unnecessary pre-vacation stress.
Technical Deep Dive (For Developers)
The n8n workflow handles the complexity while keeping the user interface simple:
// Simplified workflow logic
1. Webhook receives form data
2. Typo fixer cleans user input
3. Trip Planner AI agent generates itinerary
4. Data normalization structures output
5. Email delivery sends final plan
Each step includes error handling and fallback options. The entire system is designed to handle varying input quality and still produce useful output.
Key architectural decisions:
- Stateless design for easy scaling
- Email delivery removes need for user accounts
- Multiple AI agents for different trip aspects (activities, restaurants, logistics)
- Modular workflow allows easy feature additions
The code is pragmatic rather than elegant - optimized for reliability and user experience over developer satisfaction.
Bottom line: Sometimes the best products are born from solving your own problems. Just Wing It started as relationship diplomacy and became a practical tool that thousands of people now use to plan better vacations with less stress.