4 ways AI sharpened my NYC trip planning

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The results when using AI for anything — let alone complicated travel planning — are a bit of a grab bag. From one moment to the next, you never know which personality will field your query: the mouth-breathing space cadet or the fiercely ambitious luminary.

My AI of choice is Perplexity. I find that, after some early castigation, it can be a handy tool to help me work out some kinks in my travel planning. Here are four ways it’s helped me for an upcoming surprise trip to New York for my wife and daughter (they never read my stuff, so just keep this between us).

I have no interest in renting a car in New York. The driving itself doesn’t bother me, but parking is living hell — and exorbitant enough that I can’t justify it over rideshare.

The most expensive part is getting into the city from the airport. While musing about how to lower this bill, Perplexity threw out the idea of a limo service. They sometimes charge a flat rate for specific distances, and several include “gratuity” into the bill.

Factoring in tips and car seat-eligible Ubers, the price for a black car service was almost identical to an Uber. But the reason my ears perked up when AI suggested a limo service was because of a unique Citi Strata Elite℠ card travel benefit: up to $200 in annual statement credits toward premium chauffeur service Blacklane ($100 from January through June and another $100 from July through December).

A perk that I previously viewed as a throwaway will organically save me a whopping $100 on my commute.

Below is an example AI prompt you can use to solve a similar logistical Rubik’s Cube for your upcoming trip:

Find the best airport-to-city transportation options for [TRIP] at [TIME]. Compare every practical choice by total cost and convenience, flag any option with flat pricing or bundled fees, and end with a verify checklist for price, availability, and timing.

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I’ve got a nightmarishly ambitious NYC to-do list — and only a few days to complete it. I need to be efficient with my planning.

This is the kind of task AI was made for. I dropped all my goals into Perplexity and told it to map out the most streamlined route. In seconds, it showed me how to strategically plan my trip with the least backtracking. I could have done this myself, of course, but using AI was a big timesaver.

Here’s a simple AI prompt you can use — and paste your goals below it:

I have a detailed list of things I want to do in [CITY] over [NUMBER] days. Create the most streamlined route and itinerary, grouping nearby items together and minimizing wasted travel time.

My wife and I have multiple Resy restaurant credits to use each quarter thanks to credits from The Platinum Card® from American Express. For this occasion, I’m less concerned about the type of cuisine than the dining room. I want the most jaw-dropping atmosphere.

The “problem” is that there’s over 2,500 Resy-eligible restaurants in New York. I don’t have the time to examine each one to find the standard I’m looking for. But AI has the time. Somewhere in Arizona, a server farm has burned untold amounts of groundwater so I can decide where to have dinner a few months from now.

Again, I haven’t verified that the places it recommended were the absolute pinnacle of ambience, but it did an excellent job — considerably better than when I Googled the same question.

If you don’t plan to use your Resy credits in a big city, your nearby pickings may be slim and therefore easily scannable. But if you’ve got dozens (perhaps hundreds) of options to choose from, you can use a prompt like this:

Help me find the best Resy-eligible restaurants in New York for [PREFERENCE/OCCASION]. Give me a shortlist that best matches the goal and briefly explain why each option fits.

This approach shines when you've got dining credits to burn in a big city — AI is far better than Google at filtering hundreds of options by vibe, not just cuisine.

I’ve wanted to visit a specific pizza joint for years but have been too lazy to do it. To make a reservation, you must either line up or call the same day. Reviews suggest that if you’re not lined up hours before open, you may not get a reservation.

Perplexity alerted me to the existence of professional line standers. You can pay by the hour for someone to wait in line and make a reservation for you. It’s not particularly cheap (I’ll pay over $60 all-in), but for the convenience of simply waltzing into the restaurant with no waiting will give me several hours of the day to cross off other bucket list items.

AI has given me other neat tips, too, depending on the restaurant. Here’s the prompt you can use when you absolutely need to get in:

Find the most foolproof and time-efficient way to secure a reservation at [RESTAURANT]. Compare every realistic workaround, including paid help if it exists, and recommend the option that gets me in with the least personal effort.

That's the real value here. AI isn't just a faster Google — it's good at surfacing workarounds you wouldn't have thought to search for in the first place.

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