I used ChatGPT to plan the ultimate summer staycation — and it found experiences I never knew existed

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At some point in the near future, I’m going to hop on a plane and get whisked off to Japan so I can get a second try at enjoying its most delightful attractions.

But before I endure a 14-hour flight to my dream destination, I’m going to take some time off and use that free time to explore my home state of New York. All of my friends have been throwing out the term “staycation” as of late since they’re looking to save money by staying in their hometown but still taking the time to do some much-needed local exploring and sightseeing. That plan stood out to me as a plan worth taking since NY is home to all sorts of entertaining diversions for tourists and New Yorkers alike.

With ChatGPT as my designated “fun adviser,” I asked it to help me plan the ultimate summer staycation while taking my hobbies and interests into account.

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Not only did it handle that task with ease, but it also brought several hidden gems to my attention that I didn’t even know about before.

Using a prompt to kill my boredom and explore my home state

ChatGPT on phone

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I approached my latest “help me find tons of fun activities to do!” mission with ChatGPT with this prompt, which laid out everything that I love, my favorite foods, my preferred musical genres and more:

I want you to become my personal summer staycation concierge.

I live in or near New York and I want to experience my local area like I'm on vacation instead of simply staying home.

My interests include:

- Video games

- Japanese, Chinese, Jamaican, Italian, and Thai Food

- Blockbuster movies

- Hip-hop, R&B, rock, and house music

- Wrestling

- Museums

- Comic books

- Anime

My goals are:

- Discover hidden gems most locals don't know about

- Find unique events happening this summer

- Support local businesses whenever possible

- Mix free activities with worthwhile paid experiences

- Avoid spending my entire week and weekend indoors

- Create memorable experiences instead of simply checking off tourist attractions

Please research and build my ultimate staycation.

ChatGPT kicked off its recommendations with a great proclamation that will stay with me from this point forward:

Don't think of each outing as "finding something to do." Think of each one as an episode of a travel show where you're the host exploring a city millions of people think they already know. By combining neighborhoods, local food, independent businesses, outdoor events, and your interests in gaming, anime, comics, movies, and music, you'll come away with experiences that feel much more like a vacation than simply spending another weekend in New York.

Discovering hidden gems

central park in new york

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With a five-day staycation in mind, the chatbot listed a bunch of places to go and eat at each day. What was most surprising about those well-laid plans was how ChatGPT paid close attention to my likes to find hidden gems that I was unaware of until now. Here’s how my staycation itinerary ultimately ended up looking:

  • Day 1 - Experiencing Tokyo Without Leaving New York: Head to Flushing, Queens. Browse through the Anime Castle and Anime Figure Egg-Cellent stores. Then head to Bryant Park, Manhattan, to pay a visit to the manga store Kinokuniya Bookstore.
  • Day 2 - My Food Passport: Travel across different neighborhoods to enjoy international cuisine. Recommendations include Xi'an Famous Foods, Omar's Kitchen and Rum Bar and La Lupe Cantina.
  • Day 3 - Museum Crawl: Check out some of the lesser-known museums in New York City. Top candidates include The Paley Center for Media, the Merchant’s House Museum, and the Nicholas Roerich Museum.
  • Day 4: Hunting for Comics and Pop Culture Goodies: Check out some of the best comic book shops in the city, such as Desert Island in Williamsburg, Brooklyn, Comic Book Station in Greenpoint, Brooklyn and Midtown Comics in Times Square, Manhattan.
  • Day 5: Music Explore: Consider getting my music fix with outdoor music activities. Suggestions include SummerStage shows put on by the CityPark Foundation, attending a MoMA PS1 Warm Up electronic dance music party, and checking out any of the performers at the Summer on the Hudson arts and culture festival.

ChatGPT also pointed out the existence of an Eater’s World Fare taking place on July 18, which piqued my interest and made my stomach growl with excitement when I looked it up even further.

The takeaway

Laying out my ultimate staycation plans became less of a chore and more of a discovery session as ChatGPT showcased some cool local attractions I never knew existed.

When this current NYC heatwave dies down and cool breezes begin sweeping the city, I’ll make sure to put these plans into action and enjoy perusing through all of the now-unhidden gems I’m thankfully aware of. If you’re looking to set up the perfect summer staycation of your own, consider using my prompt and putting in your details to make it happen.


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Elton Jones
AI Writer

Elton Jones covers AI for Tom’s Guide, and tests all the latest models, from ChatGPT to Gemini to Claude to see which tools perform best — and how they can improve everyday productivity.

He is also an experienced tech writer who has covered video games, mobile devices, headsets, and now artificial intelligence for over a decade. Since 2011, his work has appeared in publications including The Christian Post, Complex, TechRadar, Heavy, and ONE37pm, with a focus on clear, practical analysis.

Today, Elton focuses on making AI more accessible by breaking down complex topics into useful, easy-to-understand insights for a wide range of readers.

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