I can no longer deny the fact that artificial intelligence will slowly begin to play a larger role in my life. It’s being used in the medical field, in the film industry, in job application systems; even my phone has begun to use AI to summarize my text messages and emails for me, which I never asked for.
As debates surrounding what AI should and shouldn’t be used for persist, I’ve gotten to thinking about what mundane parts of my day-to-day life might be better off in the metaphorical hands of a computer software. To me, if I’m going to implement AI into my lifestyle in any way, it’s going to be the boring parts that take time away from being able to do the things I actually enjoy doing, and if there’s anything I hate doing, it’s planning a weekend.
Somehow I feel intimidated by the unlimited possibilities in New York City and end up doing the same things over and over again. There are over 20,000 restaurants in the city, and Mamoun’s Falafel has probably seen me at least 20 times since I moved here almost a year ago. There are five whole boroughs, three of which I still have not been able to explore much of, which I feel very ashamed of. How can I tell people, “I love New York!” with such disappointing stats?
But enough is enough. If finding new things to do in New York is too daunting of a task for me, then it’s time I take matters into my own hands — or rather, make it a robot’s responsibility. I decided that I would try something new and ask ChatGPT, probably the most popular generative AI chatbot, to plan the perfect weekend in the city for me.
ChatGPT, with its infinite knowledge that cuts off in June 2024, will surely know all the best spots across all five boroughs and be able to give me the most ideal weekend itinerary based on my interests and guidelines, right? There’s only one way to find out.
What I asked
I figured that the more specific the prompt I put into ChatGPT, the more tailored its response would be to exactly what I was looking for. Here’s what I wrote:
“I want you to plan an hourly itinerary for the perfect weekend in New York City. I am a 22-year-old single woman who lives in Manhattan, but I am open to traveling to different boroughs. I enjoy thrifting, walking, reading and trying new foods, but I am also open to exploring new interests and hobbies. Please make sure none of the activities are too expensive — ideally, I would like to pay less than $100 for the entire weekend. My goal is to explore more of New York City and find new spots, restaurants and hidden gems. Please plan activities for both Saturday and Sunday.”
Within seconds, ChatGPT spit out a plan for both days perfectly customized to what I had asked for. “This entire itinerary keeps you well within your $100 budget while allowing you to explore different boroughs, hidden gems and new experiences! Let me know if you’d like any tweaks. 😊” it told me, emoji and all.
I won’t spoil exactly what it said just yet, but I will say I was highly impressed by the amount of detail that was included in the itinerary. The plan was separated into hours, as I had requested, and each activity had a price range next to it as an estimation for how much it would cost me. There were activities planned in Manhattan, Brooklyn, Queens and Staten Island, and each day was given a theme based on the activities it had planned. How fun!
The only red flag that immediately jumped out to me at first glance of the itinerary, however, was that there were some activities planned one after the other that seemed to be located extremely far away from each other. I’m talking Brooklyn to Staten Island to Queens-level crazy. It made me a little nervous for how I would manage to get from point A to point B within the time allocated toward each activity, but also for how much money I would be spending on transportation getting on the train multiple times a day.
Speaking of transportation, ChatGPT was also not accounting for the cost of public transit for the entire weekend, which — as we know — adds up. I decided I would keep track of exactly how much I spent during the weekend and would compare it to ChatGPT’s estimation at the end to see how accurate the AI was in planning a truly budget-friendly weekend.
Other than that, I decided to do no further research on the activities that had been generated for me so that I could really test ChatGPT’s planning prowess. I would also, to the best of my ability, follow the itinerary as closely as possible and do as many of the activities it had planned as I could so that I can truly answer the question, “Is AI capable of planning the perfect weekend?”
Saturday: Vintage Finds & Cultural Exploration
9:00 a.m. — Breakfast at a Local Bakery ($5-10)
Grab a fresh pastry and coffee at a local spot like Daily Provisions (multiple locations) or Supermoon Bakehouse (Lower East Side).
Throughout the AI itinerary, ChatGPT courteously gave me at least two options for each activity it had planned for me, which I ended up really appreciating in terms of giving me at least some control. I ended up going to Supermoon Bakehouse since I’ve already been to Daily Provisions, and part of the reason I’m doing this experiment is because I want to discover new spots in the city. The only problem is that Supermoon Bakehouse opens at 10 a.m., which I guess ChatGPT did not know, so I made the very difficult decision to sleep in a little bit and start my day an hour later than the AI had planned, which ended up working out in the end, so don’t fret.
Supermoon Bakehouse was okay. I bought two different pastries — a black forest croissant and a labneh danish — which were delicious, but also set me back $17. So that’s 17% of the budget already gone. Not the most affordable breakfast, nor the most filling — not to mention they did not serve coffee, which really bummed me out.
10:00 a.m. — Thrifting in Bushwick
Take the subway to Bushwick for some affordable thrifting at L Train Vintage, Urban Jungle and Beacon’s Closet. Check out some street art while you’re there!
None of the shops were open by the time I had made it to Bushwick, so I ended up stopping by the Brooklyn Vintage Company, which was pretty close to where I had got off the train. There were so many cool pieces to browse through, and the staff was really helpful and friendly as well. I ended up purchasing a vintage photography magazine for my best friend, who’s a photojournalist, spending a total of $21 at the store. I ended up staying an unusually long time here, so by the time I had checked out, it was already time for lunch.
12:30 p.m. — Lunch at a Hidden Gem ($10-15)
Try Bunna Cafe (Ethiopian, vegan-friendly) or Los Hermanos (amazing tacos inside a tortilla factory).
Tacos inside a tortilla factory? Sign me up. I walked to Los Hermanos and paid $11 for three carne asada tacos, which is an absolute STEAL in New York. The tacos were delicious and the service was great. There was plenty of seating available, and I was surprised to see it was not busy at all, considering it was a Saturday. Just a heads up — this restaurant only accepts cash or Venmo as payment!
2:00 p.m. — Explore Green-Wood Cemetery (Free)
Head to Brooklyn’s Green-Wood Cemetery for a peaceful and scenic walk with beautiful architecture and city views.
This was my favorite activity from the entire weekend by a landslide. Even though it was pretty cold and rainy, walking around Green-Wood Cemetery was one of the most peaceful experiences I’ve had in New York so far. I initially doubted that I would spend two hours here, but as I navigated through the 478 acres of gravestones and mausoleums, I had completely lost track of time. I even paid a visit to Jean-Michel Basquiat’s grave, which was cool. Some might find it weird that I enjoyed walking around a cemetery for so long, but it really was a beautiful place that I will definitely visit again.
4:00 p.m. — Sunset Stroll in Red Hook (Free / Pay-What-You-Wish Activities)
Walk along the waterfront and explore Pioneer Works (art gallery, often free or donation-based). Optional: Grab a $2 key lime pie at Steve’s Authentic Key Lime Pies.
We’re in the beginning of April, so a sunset stroll it was not, but it was still a lovely experience walking through Red Hook. The temperature was near freezing, and there was a slight drizzle coming down on me, but walking along Valentina Pier to get a pretty solid view of the Statue of Liberty and the Manhattan skyline was worth the cold. I also stopped by Steve’s for a key lime pie. I don’t know if someone just forgot to tell ChatGPT about inflation, but I spent $6.50 for a little baby pie. I’m not terribly mad, though — it was still really good.
Pioneer Works was also really, really cool. Though they offer free admission, they do accept donations, so I gave $10. They had an exhibition by American Artist called “Shaper of God,” inspired by the works of Octavia Butler. I really enjoyed looking at all the art and interacting with the other people there, who were all super friendly. I’ll definitely have to come back here another time.
6:30 p.m. — Dinner in Chinatown ($10-15)
Grab a budget-friendly but delicious meal at Super Taste (hand-pulled noodles) or Xi’an Famous Foods.
As soon as I took the train back to Manhattan, I was still feeling a little full from tacos at lunchtime, and I wasn’t really hungry for dinner just yet. I decided to spare myself the stomach pain and skip dinner altogether. Sorry, ChatGPT.
8:00 p.m. — Free Comedy Show or Live Music (Free / $5-10 cover)
Check out The Tiny Cupboard (Bushwick, free outdoor comedy) or a low-cost jazz show at Fat Cat (West Village).
The Fat Cat bar has unfortunately been permanently closed since 2021, but it has since rebranded as the Cellar Dog. It still has live jazz music, and because going back to Bushwick did not sound very appealing to me in the moment, I decided to make my way over to the West Village.
I should have known when I had to pay a $10 cover to get inside that this was not going to be a traditional jazz bar. It felt more like one of the bars I used to frequent during college, with pool tables and dart boards all around and colorful LEDs lighting up the place. But sure enough, there was a stage where a band called the Philip Harper Quintet was performing. The audience was seated on what looked like wooden church pews, sipping beer from plastic cups and speaking loudly over each other and the music. This was not the jazz experience that I was expecting, and I felt a little awkward sitting there by myself. But hey — the band was great, so I guess that’s a win. I did not stay very long, though, and ended up making my way back home after an hour to call it a night for day one.
Sunday: Books, Parks & Hidden Gems
9:30 a.m. — Brunch in the West Village ($10-15)
Try Buvette (French café) or Coppelia (24-hour Cuban diner with amazing breakfast).
Just by glancing at the schedule for day two, I could immediately tell I had a long day ahead of me, so it was important I grabbed a decent breakfast to keep me going for the rest of the day. I had heard great things about Buvette, so I was interested in checking it out.
I got to the café at 9:30 on the dot, just before a line had begun to form. I only had to wait about five minutes to be seated, after which I was led to a seat at the bar, where I could watch the chefs make all the meals and brew drinks from the comfort of my barstool chair. I ordered two cappuccinos (I was really tired) and a plate of eggs on toast with goat cheese and sun-dried tomatoes, all of which were delicious. There were multiple solo diners at the restaurant reading books while they sipped on their drinks and ate their breakfasts, so I didn’t feel super awkward being there alone. 10/10, would dine again.
11:00 a.m. — Visit a Hidden Bookstore (Free)
Check out Codex Books (LES), Unnameable Books (Brooklyn), or Housing Works Bookstore (SoHo).
Housing Works Bookstore isn’t necessarily what I would call a hidden gem, so I decided against visiting that one. Once again, ChatGPT did not inform me that Codex Books would open at noon, so that left Unnameable Books as the only option left.
I took the train back to Brooklyn and walked a few more minutes over to Unnameable. The bookstore itself was quaint and cramped, but in an oddly good way. The diverse array of books was so exciting to browse through, and I ended up purchasing a Joan Didion book and a collection of stories from Palestine, spending $28 total on the two books. This was a great suggestion by ChatGPT, so throw another point on the scoreboard.
12:30 p.m. — Picnic in Prospect Park ($5-10 for snacks)
Pick up some affordable snacks from a local deli and relax in Brooklyn’s most beautiful park.
I wasn’t really hungry, so I skipped the deli and went straight to Prospect Park, which turned out to be a great break in between activities; I sat on a park bench by Long Meadow and started reading one of the books I had just bought for a couple of hours. Definitely not a bad suggestion from ChatGPT, and definitely right up my alley.
3:00 p.m. — Ferry Ride to Staten Island (Free)
Take the Staten Island Ferry for stunning skyline views at no cost!
The Staten Island Ferry has been on my bucket list since I moved to New York, so I was excited for this one. After boarding the ferry, I sat on a bench on the outer edge as it made the 20-minute journey to Staten Island and as I took in all the incredible views of both Manhattan and Brooklyn. I even got a pretty close glimpse of Lady Liberty herself. Though this was probably the most touristy item on the AI agenda, I still had a good time and ended up taking tons of pictures.
5:00 p.m. — Dumplings in Flushing ($10-15)
Hop on the 7 train and enjoy some of NYC’s best dumplings at White Bear or Tianjin Dumpling House.
So this is the point of the weekend where I started to drift off the path that the AI had paved for me. Once again, Tianjin Dumpling House has been permanently closed since the pandemic. Luckily, ChatGPT gave me another dinner option! Unluckily, it was an hour away.
At this point, I was dead tired, and the idea of going to Queens from Staten Island sounded miserable and unrealistic, so I’m sorry to say, dear reader, but I did not go. I’ll have to try these incredible dumplings another day when I’m actually up for the commute.
Since I was on Staten Island, though, I decided to hit up my friend Alli, a Staten Island native, to see if she wanted to grab dinner. She took me to a gastropub called The Hop Shoppe, which was pretty fun! The music was great, and I enjoyed my buffalo mac and cheese. I had a lovely time catching up with a friend and getting to see glimpses of Staten Island for the first time. Afterward, I took the ferry back to Manhattan and went home.
Was it worth it?
I can safely say that this was definitely the most eventful weekend I’ve had since moving to the city. I logged over 40,000 steps between Saturday and Sunday — maybe the biggest win of the weekend.
ChatGPT claimed I would spend less than $100 the entire weekend, not accounting for transportation costs. After tallying up all my expenses, I spent a total of $217.17 across the two days; with 10 trips on either the bus or the train, that’s 13% of what I spent going toward transportation alone, and it would have cost me more if I had done everything on the itinerary. Yeesh. While there were some activities that I anticipated spending a little bit more on, like thrifting and book shopping, it seems to me that ChatGPT’s knowledge of how much things cost in the good year of 2025 is a little outdated, so if you attempt to do something like this yourself, take a little extra caution with the cost estimates the AI bot gives you.
The best part of this experiment was how the AI was able to introduce me to a bunch of great new spots in the city that I was unfamiliar with before this weekend, and it forced me to leave my apartment and explore the city more, an idea that used to exhaust me and stress me out. While there were some parts of the plan I ended up not sticking to, the ones I did were super enjoyable, and I was even able to go visit a friend I hadn’t seen in months.
While I probably wouldn’t ask AI to create an entire daily schedule for me again, I think it’s a great resource for discovering new places and restaurants if the thousands of options are too overwhelming and you need someone — or something — to just pick for you. I’d highly recommend being as specific as possible when entering your prompt into ChatGPT about your exact needs and wants so that it can find some options that actually work for you. I’d even go so far as to specifically ask for activities in the area you know you’ll be in so you don’t receive dinner options an hour away from you.
Thank you, ChatGPT, for the experiment of a lifetime. I can’t say I’ll be trying this again, though.