TL;DR
- AI skeptics planned their entire Spain honeymoon with ChatGPT - it exceeded every expectation
- ChatGPT suggested San Sebastian over Madrid based on their preferences (they’d never considered it)
- AI provided day-by-day itinerary, packing lists, restaurant recommendations, and Spanish phrases
- Best for: Travelers overwhelmed by research who want personalized suggestions beyond generic guidebooks
- Key lesson: AI asks questions you wouldn’t think to search for - like optimal layover lengths for jet lag
A couple who’d never used AI for anything practical planned their entire honeymoon with ChatGPT - and it found a hidden gem destination they would have overlooked with traditional research.
Jon and Lisa had never used AI for anything practical.
They knew it existed. They’d seen the demos, the hype, the debates. It felt abstract — a tool for programmers and writers, not regular people planning a honeymoon.
Then Jon got curious.
Their honeymoon was important. Two weeks in Spain, a trip they’d remember forever. Getting it right mattered. The research was overwhelming: flights, hotels, restaurants, activities, packing, timing.
“I thought, why not ask ChatGPT? If it’s terrible, I’ll ignore it.”
It wasn’t terrible.
The First Query
Jon started with flights.
“We’re flying from Boston to Spain for a 12-day honeymoon. We want to visit Barcelona and a second city. Budget is moderate — not cheap, not luxury. What are our flight options and what should we consider?”
The response was detailed. ChatGPT outlined several approaches:
- Direct flights to Barcelona, then train to second city
- Open-jaw itinerary (fly into Barcelona, out of Madrid)
- Which airlines served the route
- Typical price ranges for different booking windows
- Time of year considerations
But the surprising part was the nuance. The AI discussed layover lengths that would cause stress versus ones that allowed comfortable connections. It mentioned that arriving in the morning helped with jet lag versus evening arrivals.
“It sounded like advice from a seasoned traveler, not a database lookup.”
The Second City Decision
They’d assumed Madrid would be their second stop. ChatGPT pushed back.
“Madrid is a great city, but given that you mentioned wanting romantic scenery and historic architecture, you might also consider Seville, Granada, or San Sebastián. What are your priorities?”
They hadn’t asked for alternatives. The AI offered them anyway.
After describing their preferences — walkable streets, historic sites, great food, intimate atmosphere — ChatGPT recommended San Sebastián over Madrid.
“We’d never considered it. We would have gone to Madrid by default. The AI suggested something we didn’t know we wanted.”
They researched San Sebastián. Beautiful coastal city. Michelin-starred restaurants everywhere. Basque culture distinct from the rest of Spain.
They changed their plans.
The Hidden Gem Effect
Jon asked ChatGPT for restaurant recommendations in San Sebastián.
The AI provided both famous spots (like Arzak, the legendary restaurant) and lesser-known options. It flagged pintxos bars worth visiting, suggested neighborhoods for evening walks, recommended a specific bakery for morning pastries.
Some suggestions came from guidebooks. Others seemed sourced from deeper knowledge — the kind of tip you’d get from a local friend.
“We went to a restaurant called Zim that ChatGPT suggested. It wasn’t in any guidebook we’d found. It became the best meal of the trip.”
The AI had “uncovered hidden gems we might have passed over” — places that didn’t rank high in search results but matched their specific preferences.
The Detailed Itinerary
Eventually, Jon had ChatGPT build a complete day-by-day itinerary.
“Create a 12-day Spain honeymoon itinerary. Days 1-5 in Barcelona, days 6-10 in San Sebastián, days 11-12 for travel home. Include breakfast spots, activities, dinner reservations needed, and downtime each afternoon.”
The AI produced a full schedule:
- Day 1: Arrive morning, walk neighborhood, light lunch, siesta, dinner at specific restaurant
- Day 2: Sagrada Familia (book morning tickets), lunch near Gràcia, afternoon at Park Güell, dinner in El Born
- Day 3: Gothic Quarter morning, beach afternoon, tapas evening…
And so on. Each day had specific suggestions, booking requirements flagged, alternatives for bad weather.
“I tweaked it. Swapped some restaurants. Added a museum. But the structure was there. Building it from scratch would have taken days.”
The Packing List
Lisa asked for help packing.
“12-day Spain trip in September. Barcelona and San Sebastián. Mix of city walking, beach days, nice dinners. What should I pack?”
The AI provided a detailed list organized by category:
- Versatile pieces that worked for multiple occasions
- Layers for variable September weather
- Walking shoes that looked nice enough for restaurants
- Specific items for beach days
- Toiletries to bring versus buy there
- Tech (adapters, chargers, portable battery)
- Documents and copies to carry
It even suggested: “Consider bringing a small bag for groceries or beach supplies — San Sebastián’s food market is worth visiting.”
Practical. Thoughtful. The kind of tip that makes travel easier.
The Language Prep
Jon asked ChatGPT to teach him essential Spanish phrases.
“Give me 15 crucial phrases for traveling in Spain, focused on restaurants, directions, and common courtesies. Include pronunciation guide.”
The AI provided:
- Ordering phrases (“Una mesa para dos, por favor”)
- Asking for recommendations (“¿Qué nos recomienda?”)
- Getting the check (“La cuenta, por favor”)
- Basic courtesies (please, thank you, excuse me)
- Emergency phrases (where is, I need help)
Each with pronunciation hints and usage context.
“I practiced on the plane. When we landed, I could handle basic interactions. Made everything feel more adventurous.”
The Result
The honeymoon exceeded expectations.
San Sebastián was magical. The restaurants ChatGPT recommended were excellent. The packing list was nearly perfect. The itinerary balanced activity with rest.
Jon’s reflection: “I felt incredibly confident about every aspect of our trip, and it went off without a hitch.”
The confidence mattered. Instead of second-guessing decisions, they enjoyed the trip. Instead of researching mid-vacation, they were present.
“Our honeymoon would have been good regardless. But the AI made it better. Less stress, better choices, more discoveries.”
The Convert
Jon uses ChatGPT for travel planning now. Every trip starts with AI consultation.
He’s learned the nuances:
- Verify specific details (AI might have outdated info)
- Ask follow-up questions to refine recommendations
- Combine AI suggestions with traditional research
- Use it for logistics, rely on instinct for experiences
“It’s not perfect. Restaurant info can be out of date. Hours change. Some suggestions are generic. But as a starting point? Unbeatable.”
He estimates AI planning saved 15-20 hours of research. More importantly, it asked questions he wouldn’t have thought to ask.
“‘What should we consider for layovers?’ I wouldn’t have searched for that. The AI volunteered the insight.”
The honeymoon taught them that AI wasn’t just a curiosity. It was practical. Useful. A tool that made the most important trip of their lives better.
That conversion — from skeptic to user — came from one simple truth: “It worked. That’s all that matters.”
