The Week I Let ChatGPT Plan My Travels Inside Singapore

This Week:

  • An exciting final couple of days in Bali – a Christmas villa, an expensive dinner, and exploring the local side of the island
  • The problem I have with travel planning and how I solved it with a personalized reusable template and ChatGPT
  • My first 2 days exploring Singapore!

December 2023

Su M T W Th F S

Where In The World Was I?

  • Canggu, Bali, Indonesia
  • Beraban, Bali
  • Serangan, Bali
  • ✈️ Denpasar (DPS) to Singapore (SIN)
  • Singapore

Live Travel Map 🌎

Metrics From The Week

👆Realizing how hard it is to keep up a consistent sleep schedule without a routine 😬

The Christmas Villa

Merry Christmas from Bali! A bunch of people from the hostel organized a villa to spend Christmas Eve + Christmas together.

It was about 45min by motorbike northwest of Canggu.

I got to see the REAL local side of Bali.

The villa was this beautiful 6 or 8 bedroom villa, multiple buildings around this center courtyard and pool.

I ended up chatting with this guy who was staying in the same dorm room as me back at the hostel. It was great, I felt like I finally met another like-minded person to me.

He said he works ~10 hours a day, every day, because he loves what he does. Our conversation reminded me a lot of meeting The French Guy™️ a couple weeks ago.

I really wanted to be around this guy, to get in my network, I just (again) couldn’t quite figure out the value that I could provide to him. There was lots more I was interested in hearing about from him, but we didn’t get as much time to talk as I wanted.

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Christmas morning from paradise. Feliz Navidad!

Saying Goodbye

After almost 2 months… I finally checked out of Tribal 😢

I said goodbyes to some people I met as well as the staff at the hostel. One of the waitresses/staff who learned my name waited for me and said goodbye 🥹

I got lunch at Roots this day, the second in a row. On my way out, the waiter said “see you tomorrow!” And I said “aww, I’m leaving today!”

Gosh, everyone is so nice here. It felt like leaving my family. I got a little choked up on my way out.

I’ll be back soon!

Back to my 2 backpacks:

I took a Grab taxi to Serangan Island to a hostel that’s MUCH closer to the airport. Took me 2 hrs to get to the hostel, so I’m really glad I went a day early!

I took a walk around the neighborhood and ran into a park/soccer field with a bunch of kids playing soccer together and messing around.

I smiled as I walked by, one of the little kids waved at me and said “Halo!”

After something like 2 months of learning Indonesian on Duolingo and only living in the touristy area of Bali, this was my moment 😂

“Halo!” I said.


“Apa kabar?” (How are you?)

“Baik” (good) he said, smiling.

Napoleon Dynamite Yes GIF - Find & Share on GIPHY

I got dinner (see food later in the post) in Sanur (east side of the island, ~15 min motorbike from the hostel) and walked around.

The End Of A Chapter

What a chapter this has been… I did some reflecting on the last 2 months as a whole and wanted to share the biggest things I learned. I thought it might be a good morning video and liked how it turned out!

Food From The Week (Bali)

  • Brunch Club – breakfast sandwich, souffle pancakes, kombucha, juice ($17.99)
    • Sandwich was a bit too big to handle, pancakes were delicious! Super light and fluffy, not too sweet
  • Roots (x2) – fully vegetarian/vegan restaurant – wrap, grain bowl, ginger beer ($17.69); another wrap, grain bowl, beetroot pancakes ($22.96)
    • Nothing like stuffing myself with plant-based food, it was all delicious
  • WOODS – Christmas dinner – vegetarian pizza souffle, beef tenderloin, polenta fries, juice ($45.68)
    • Pizza souffle was… interesting, not sure what I was expecting though, like an crunchy airy cracker with a bit of spice; the beef tenderloin was u n b e l i e v a b l e. Holy sh*t that was good. Worth the pricetag
  • Massimo Italian Restaurant – pasta, garlic bread, ice cream sundae ($16.18)
    • Eh, got the job done. The cherry ice cream sundae I think was the best sundae I’ve had in my entire life. Anything cherry = instant purchase

✈️ Off To Singapore!

The goal here: break the routine with a bit of vacationing/exploring before I jump back on the grind

The past summer I got a travel credit card with Priority Pass lounge access and wow, airports have started to actually become enjoyable now, not stressful and uncomfortable places from hell. I feel very grateful to be able to say that. I ate a free meal at a restaurant (it was actually pretty good!) and got some free snacks in the lounge.

Singapore has these new automated immigration machines that are crazy cool.

All I had to do was fill out this Arrival Card form (flight info, when I’m arriving and leaving, etc.), then at the immigration checkpoint, I just scanned my passport, did my thumbprint, and I was through in like 20 seconds.


You can see them on the left side of this picture:

First Impressions Of Singapore

  • So many shopping malls
  • So many nice cars
  • It’s so green!
  • And it’s so clean! I’ve been here 5 days and I think on Thursday I remember seeing a single plastic cup on the ground.
  • I like it so far!

I Need To Solve This Problem

A lot of areas of my life, I plan a lot, I like control, and I’m incredibly detailed.

Travel is one of the few areas where this is NOT the case. I’m not too sure why it’s ended up this way.

More often than not, planning traveling ends as getting into a state of paralysis, decision fatigue, and frustration.

Ya know when you’re at a huge-a** store like Walmart looking for a single item, like a caesar salad dressing, and you go to the salad dressing aisle and there’s like 14 different salad dressings that are ALL CAESAR DRESSING.

You’re standing there in the middle of the aisle thinking, first off, why the hell are there 14 different brands of caesar dressing, but secondly, which do I pick? The healthy looking one? Oh but it’s $11 per bottle. Maybe I’ll just go for the cheap one for $2.50. Ah but it’s got a bunch of crap ingredients. What about the one with the pretty picture of a field on the front of it for $4? Wait but how is this one different from the one that’s also $4 but it has a picture of a bowl of caesar salad on it?

And then after 15 minutes of standing there confused, you walk away without any caesar dressing in your basket.

Well that’s how I feel when I try to plan my travels.

There’s literally infinite things to do.

Every blogger lists their top 10 things to do in [insert city], but there are some things I just don’t like doing. I’m not a big history person, so spending all day in a history museum reading wall plaques frankly sounds like torture.

I also would rather walk through a quiet local neighborhood than go to a bunch of tourist hotspots surrounded by people snapping their “See, I was here!” photos.

This past summer in Europe, I pretty much planned nothing (except for the music festivals). Whenever I got to a city, I’d look on Google Maps and just pick some cool looking places from what I saw there.

But I frequently ended up with this feeling that I “could’ve done better” to explore the city.

My dream is to have a personal travel planner, something I heard Bill Perkins (he wrote the book Die With Zero) talk about.

I just want to get a notification that everything is booked and that I just have to show up at the airport on Thursday afternoon.

But I can’t afford that yet, so the next best thing? ChatGPT.

The problem is that ChatGPT doesn’t know me and my travel preferences. If I ask for “3 days in Singapore” it’s just gonna give the generic advice. I want “3 days in Singapore” for Peter. I want it to give recommendations personalized to ME.

This week I ended up finally putting together this “Travel Profile” document that has a ton of information about my travel preferences.

The goal is to be able to say: “Plan 3 days in Singapore. Here’s my comprehensive travel profile:” then copy+paste it right in that way it gives me personalized recommendations.

And that’s exactly what I asked and BOY was that cool to see it run.

I literally didn’t fact check anything. I just took the exact itinerary, put it into a document, then mapped it out into a Google My Map so I could use Google Maps. The only things I added were a couple optional activities that I got from my hostel.

Funny how this is exactly the vehicle I’ve been pursuing with this business venture the past 2 months: Google My Maps + Travel Itineraries. I thought, this map is literally so valuable for me, why don’t other people find it valuable? 🤷‍♂️

So with all the context aside, let’s get on to exploring Singapore!

Day 1 in Singapore: City Exploration and Cultural Landmarks

  • Explored the streets of Chinatown
  • Ate at the Maxwell Hawker Center
    • THAT was cool – so many food stalls, everyone eating. I had this expectation that these food stalls would be like the street food in Bangkok – kind of questionable but you go for it anyway. But here in Singapore, the health and food standards are pretty high so I felt way more confident.
  • Went to the Buddha Tooth Relic Temple
    • Something I probably wouldn’t have done but was really cool! So many buddha statues!
  • Walked through the financial district and along the water.
  • Took a pic with the Merlion and the view of the famous Marina Bay Sands
  • Walked along the Boat Quay
  • Spent the evening exploring the Clarke Quay and Robertson shopping mall/districts

Day 2: Nature, Relaxation, and Art

  • Walked the Singapore Botanic Gardens
    • See, most people already probably knew this is a UNESCO World Heritage Site, but I didn’t! Because I didn’t do a research beforehand! I just showed up! Finding that out was cool.
    • The grass is different here, I still can’t get over that 🤯
  • Got lunch and walked the fancy Orchard Road
  • Walked through the courtyards of the Raffles Hotel
  • Walked through Esplanade Park to see the financial district skyline and the Boat Quay from across the river
  • Changed hostels
  • Went to the quiet neighborhood of Tiong Bahru, saw the hawker/food center, went to the bakery and just chilled in the evening

So, How’s It Going?

How’s my new personalized travel planner? Is it working?

A resounding yes.

It feels so unbelievably good to just look at my itinerary and map and not have to decide what to do next. I’m just doing what ChatGPT told me to do. AND, I just trust it because it knows what I like and it told me WHY it recommended each thing.

That said, I did veto one thing yesterday – going to the Art Museum. It said to focus on their landscape photography exhibits (which, is something I love to do, a good recommendation), but they didn’t have any good photography exhibits.

I realized something that first day of exploring though.

Because I didn’t plan anything, I didn’t have any expectations. I hadn’t done any research beforehand, I hadn’t seen pictures of what things would look like, I didn’t know what to expect.

Thus, everything was new, everything was fresh. I could just be present in the moment and appreciate the places I went to because I wasn’t comparing things to what I had seen online.

And I liked that.

I do still have a lot of friction trying to pick out restaurants to eat at. I have some ideas for how to get better recommendations but I’m still working on that.

I also know there’s lots more context to add to it and tweaking to do, but this is just the first version I can iterate from.

It’s hard to tell if my enthusiasm comes across in words, but this is LITERALLY a game-changer for me. I’m so excited.

Food From The Week (Singapore)

  • Kiwami: Ramen & Gyoza Bar – lunch set: ramen, gyozas, ice tea ($20.71)
  • Thai Kha (Thai Street Cuisine) – pad see ew, spring rolls, mango sticky rice ($23.00)
  • Guzman Y Gomez – burrito bowl, chips ($12.88)
  • Maxwell Hawker Center Vietnamese Place – vermichelli noodle bowl, banh mi sandwich ($9.50)
    • Delicious! Like com’onnnnn all that for $10!
  • Wildfire Burgers – burger, fries, fried chicken ($25.29)
    • Eh
  • Teppei Syokudo – build your own bowl ($11.39)
  • Nunsaram Korean dessert cafe – bingsu (shaved ice) dessert ($12.46)
    • Oh, my, LORD was this good. It looks like an absolute carb bomb that’s incredible sweet, but it’s the opposite. Light flaky shaved ice, creamy mango ice cream, ripe mangoes around the outside, with condensed milk (or coconut cream?) drizzled over the top. The sweetest part of this was the actual mangoes… Heaven.
  • Sawasdee Thai – drunken noodles, spring rolls, thai iced tea ($27.07)
    • Bit of a tourist trap but everything was good!
  • Dome Bakery – warm fudgy brownies ($10.25)
    • Tasted as good as it looks. Warm gooey inside, cakey outside. Amazing.

*Prices in USD

Business Progress Update

The travel blogger business venture research and analytics offer is still on hold while I’m in Singapore and doing my end-of-the-year productivity optimization.

Productivity Optimization

This week I broke down all the tasks I would like to do, prioritized them using the frame: “Will this make me more efficient” then started working.

I’ve already made some pretty huge improvements! Nice.

Thoughts From The Week

Back to my morning journaling in coffee shops

I’ve lost pretty much all of the structure, routine, and good habits I had in Bali. I spent the last 2 months so focused and made so many improvements. Some of this was partly the objective of this week in Singapore, but at the same time, it’s a bit disappointing to see all those improvements basically tossed in the trashcan.

I can already feel the changes in willpower and restraint. I won’t put ALL the “blame” on environment, but it’s really amazing how much my physical environment makes a difference.

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What’s Next?

Off to Kuala Lumpur this week!


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