How to Hack Puerto Rico Travel Costs with a Little AI Assist
When I started planning my solo trip to Puerto Rico, I had two conflicting desires: I wanted to stay in the heart of Old San Juan but also experience a little resort luxury—all without obliterating my budget. So, like any modern traveler, I turned to ChatGPT for some ideas.
Spoiler: It worked.
Step One: Asking the Right Questions
My first instinct was to book a hotel, but after a quick chat with Chattie (yes, I’ve named it), I started thinking differently. I asked, “How can I experience resort-style perks in Puerto Rico without staying at one for a full week?” and that’s when the real brainstorming started.
AI helped me break it down:
Stay in an Airbnb in Old San Juan (more affordable, more character, access to local markets for groceries).
- Book RESORTPASS day use passes instead of committing to a full stay.
- Prioritize experiences over lodging costs.
This was exactly the mix I was looking for—local immersion with just enough luxury sprinkled in to feel like a vacation.
Step Two: Finding the Best Deals
From there, I used ChatGPT to help me narrow down which resorts offered day passes and which neighborhoods in Old San Juan would be most convenient for walking, eating, and avoiding overpriced tourist traps. I cross-checked everything online, and sure enough, the advice held up.
I ended up booking ResortPass ticket to The Royal Sonesta and Condado Plaza, which meant I still got my fill of poolside cocktails, infinity pools, and beach access—but only on the days I wanted it. The rest of the time, I was wandering cobblestone streets, snapping photos, and living like a local.
The Real Hack: Balancing Budget and Experience
Here’s what I learned: You don’t have to drop thousands on a resort to have a luxurious experience. A little research (and a little AI help) can stretch your budget without sacrificing the fun stuff. By spending less on accommodations, I freed up cash for things that actually made the trip memorable—like great food, fun excursions, and, let’s be honest, plenty of mojitos.
So, if you’re torn between budget travel and a bougie getaway, just know you can absolutely do both. All it takes is a little creativity… and maybe a quick chat with Chattie.
