I usually love planning my journey all the way down to the little particulars. It is thrilling to resolve prematurely the place to eat and how one can get there, and ensure I do not miss out on any must-see sights and sights.
Nevertheless, I just lately booked a last-minute journey to Las Vegas with a TPG colleague and located myself overwhelmed by the choices. Having by no means visited Sin Metropolis earlier than, I struggled to get my head across the sheer variety of eating, lodging, transport and leisure choices.
With little time to place collectively my weekend plans and with out feeling the identical enthusiasm or motivation I had for planning extra bucket-list holidays, I made a decision to roll the cube and put my religion in ChatGPT. With a number of prompts like dates, pursuits, price range and prebooked tickets, I let this more and more standard private assistant do the analysis for me.
So how did it go?
Some gambles paid off handsomely, whereas others had been spectacular failures.
Associated: I gave ChatGPT full management of my European metropolis break. This is why I would not do it once more
What labored: Straightforward to learn, nice concepts on paper
ChatGPT requested a handful of smart clarification questions as I fed it some fundamental details about my weekend in Vegas and my private preferences, reminiscent of the kind of meals I appreciated consuming and the way a lot I needed to spend on meals.
Inside seconds, it was capable of lay out a neat, digestible and seemingly logical itinerary for my three-night journey. It additionally provided to supply a map exhibiting the situation of every thing it had urged, so I might see the place I’d be going every day, which was a useful function and one thing I hadn’t thought-about when planning my journey.
I confirmed my “AI-tinerary” to TPG’s managing editor of newsletters, Becky Blaine, who’s a Las Vegas knowledgeable, prematurely of my journey.
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She referred to as the itinerary “stellar” for a first-time customer, so I assumed I used to be off to a great begin.
What labored: Implausible resort comparisons
I needed to redeem Hilton Honors factors for my keep in Las Vegas, and there have been loads of choices out there. Primarily based primarily on pricing and places, I narrowed them all the way down to the Conrad Las Vegas at Resorts World and the Waldorf Astoria Las Vegas and requested ChatGPT to clarify the variations and which might be extra appropriate for my journey, as they value comparable quantities of Hilton Honors factors every night time.
ChatGPT did a improbable job of summarizing this shortly, effortlessly and logically for me, with the primary variations being that the Waldorf Astoria doesn’t have a on line casino, has a quieter vibe and is a bit more upmarket than the Conrad.
As a first-time customer to Vegas, I sought the taking place, flashy on line casino expertise, so I opted for the Conrad, which proved to be an important alternative. I particularly cherished the huge array of meals and beverage choices out there contained in the Resorts World advanced, and the pool space was superbly designed and really enjoyable within the Nevada sunshine.
I saved a number of time by combing by means of evaluations of each properties utilizing synthetic intelligence, and I’ll undoubtedly be utilizing this once more to match lodging choices sooner or later.
Associated: The most effective inns in Las Vegas for a Sin Metropolis getaway

What labored: Eating choices with appropriate options and costs
I had heard horror tales about how this once-affordable vacation spot had grow to be considerably costlier, and I used to be eager to not waste some huge cash on meals and drinks.
I used to be impressed with how ChatGPT was capable of take my easy need and discover appropriate eating choices, additionally offering particulars reminiscent of delicacies, estimated costs and places inside main inns.
It additionally recognized a number of joyful hour choices that I might discover if I needed to save cash on drinks, together with Electra Cocktail Membership and Brera Osteria, each at The Venetian Resort Las Vegas.
We ended up going off-script at a few bars that weren’t on the itinerary, just because they “seemed enjoyable” as we walked previous. Once I realized they served $15 beers and $30 cocktails (earlier than tax and tip), I knew I ought to have paid nearer consideration to my fastidiously crafted itinerary.
As my resort reserving included a Hilton Honors Diamond every day food-and-beverage credit score, I included this within the ChatGPT prompts, figuring I might avoid wasting cash every day.
My ChatGPT itinerary added a wise suggestion that I might seize a snack or welcome drink at Resorts World proper after checking in and use this credit score, as I used to be more likely to be hungry after the lengthy flight from London.
This was an effective way to avoid wasting money earlier than the weekend actually kicked off.

What did not work: No consideration of main occasions
I included a immediate that I had booked a rental automobile for the day to drive out to Valley of Fireplace State Park for mountaineering. Distances, even between inns, may be huge in Las Vegas, so I discovered a automobile to gather at Circus Circus Resort & On line casino, which was proper subsequent door to Resorts World.
ChatGPT helpfully urged it was a simple, quick stroll from the Conrad throughout the street to Circus Circus. Though I had supplied the situation and date and time of amassing the automobile, ChatGPT’s analysis didn’t account for a 60,000-person music pageant that was opening its gates on the identical time on the Las Vegas Competition Grounds, which may be very near Circus Circus and the place many festivalgoers had opted to remain.
Because of this, I encountered absolute chaos, with hundreds of music followers streaming by means of the resort, the resort automobile park (the place the automobile was) and close by roads. It additionally took considerably longer to drive out of and again into Vegas as there have been a number of street closures, diversions and really heavy site visitors, which threw our schedule off at each the beginning and finish of the journey.
I want ChatGPT had been savvy sufficient to understand that this main occasion, which coincided with my particular location at the moment, would have an effect on our itinerary.
Associated: The newest attraction in Vegas? Dynamic pricing at resort foyer retailers

What did not work: Suggesting the very best methodology of transport
From what little I knew, Las Vegas usually catches first-time guests off guard by making them assume they will simply stroll the size of the Strip, underestimating its precise distance.
Due to this, I requested ChatGPT to counsel the very best methods of getting round. It shortly urged utilizing a ride-hailing service each time I wanted to maneuver anyplace, which did not seem to be probably the most cost-effective strategy to spend the weekend. Once I queried this and requested about strolling distances versus driving, among the choices had been a 15-minute stroll versus a 7-minute drive, and it appeared unusual that anybody would suggest ordering a automobile when factoring within the wait occasions and the truth that with these enormous resort casinos, the designated ride-hailing service location was nowhere close to the foyer, nor my room.
For instance, after checking in at Conrad Las Vegas, I needed to get to Treasure Island Resort & On line casino, the place I had tickets to a Cirque du Soleil present at 6:30 p.m. Friday. I am glad I ignored the preliminary ChatGPT recommendation to take an Uber or Lyft as a result of:
- It was a simple, flat 25-minute stroll (I might see Treasure Island from my room on the Conrad).
- The timing was throughout sundown in October, when the climate was good and the “golden hour” lighting spectacular, for my first-ever foray onto the well-known Las Vegas Strip.
- It was throughout the night site visitors rush hour, when it would take a while for a automobile to reach on the resort, I might want to permit further time for site visitors (or danger lacking the beginning of the present), and the price of the experience throughout this peak time might be larger than ordinary.
As an alternative, I took a magical sundown stroll alongside the Strip, which was nice to stretch my legs after the lengthy flight.
Associated: Affable service, glamorous widespread areas and mediocre rooms: My weekend on the Las Vegas Hilton at Resorts World

What did not work: En route was not en route
The largest ChatGPT fail of my Las Vegas weekend was throughout our drive to Valley of Fireplace. Whereas the state park itself is spectacular, extremely really helpful and effectively definitely worth the hour or so drive from the town, I had requested ChatGPT to suggest someplace to cease on the way in which again to the town to seize some lunch after our hike.
Including prompts that I would really like a themed diner expertise, it shortly urged Cablp, owned by well-known magician Criss Angel. This appeared like a good suggestion, nevertheless it wasn’t till we put the diner’s title into Google Maps after our hike that we realized it was most undoubtedly not “en path to the town” as my ChatGPT itinerary had promised, however somewhat a 20-minute drive in the other way.
We weren’t all for including 40 minutes of driving to get a burger, so we needed to discover an alternative choice on the final minute that was really en route again to the town.
I am mystified as to why ChatGPT would think about a 20-minute drive past the vacation spot to be “en route.”

What did not work: Vegas is not the very best vacation spot for a structured itinerary
In the end, my greatest lesson from utilizing ChatGPT for an extended weekend was that Sin Metropolis wasn’t the best vacation spot for a structured, hour-by-hour itinerary. Whereas ChatGPT supplied detailed directions, it proved too inflexible for a metropolis the place we threw warning to the wind.
After a number of free-pour-strength cocktails and a few wins on the roulette desk, we quickly forgot the itinerary in favor of merely seeing the place the night would take us.
Moreover, since I used to be touring with somebody who had briefly reviewed the itinerary however not contributed considerably to it, it did not make sense to always examine ChatGPT for directions and drive my colleague to observe the itinerary precisely; somewhat, I might merely ask them what they most popular.
I anticipate that utilizing ChatGPT to create a journey itinerary would work higher for solo vacationers, who needn’t examine in with what others wish to do, in addition to for locations the place sticking to strict schedules is extra acceptable, reminiscent of Tokyo or maybe Germany.
What did ChatGPT be taught from this expertise?
I loaded these ideas into ChatGPT and requested the platform to supply some commentary on my scorecard of what labored and what did not.
This is what it needed to say:
- Thanks for the considerate debrief. The plan was scaffolding, not a script. We iterated round your constraints so the framework might flex whilst you improvised.
- Relating to transportation, the preliminary itinerary urged utilizing a ride-hailing service. After you requested, it transformed rides beneath 20 minutes to strolling and pinned routes on a map, so you could possibly select dwell as a substitute of defaulting to automobiles.
- On the Circus Circus pickup: actual‑time occasion detection (e.g., the music pageant) wasn’t enabled except we had been requested to browse native calendars; truthful critique — I ought to proactively flag main‑occasion zones round pickup factors.
- On “en route” to Valley of Fireplace: you requested a themed diner; decisions are sparse on that hall. CABLP match the transient however was a detour; the map uncovered that. I ought to have labeled it clearly as non-obligatory with the gap famous.

Backside line
Positive, I in all probability might have squeezed a bit extra in and saved a number of extra {dollars} by following my ChatGPT Las Vegas itinerary to the letter, however I ticked off the primary gadgets and had an absolute blast for my first go to to Sin Metropolis.
I am eager to return, maybe subsequent yr, however I might additionally prefer to discover extra of the previous facet of Vegas subsequent time. Whereas it was decadent staying at Conrad and attending exhibits on the glittering Bellagio Resort & On line casino and eating on the Venetian, I used to be charmed by the kitsch character of the likes of Circus Circus and Excalibur Resort & On line casino, to not point out they might be considerably cheaper than the place I stayed.
The buzzing Fremont Road Expertise was very well completed, and bouncing across the Golden Nugget Resort & On line casino and making a number of wagers Saturday night time was terrific enjoyable, even when my reminiscences are a little bit hazy after the solar went down.
I’d undoubtedly flip to ChatGPT for some help in placing collectively the journey subsequent time, however I would not be on the lookout for hour-by-hour directions.
My finest recommendation for Las Vegas is to roll the cube and float, and hopefully you will come up trumps.