The fix for coming up a few thousand miles short

Traveler pressing down on an overstuffed suitcase next to another suitcase

by Sarah Silbert

Sarah has covered credit cards and award travel for over 10 years. She's contributed to The Points Guy, Fortune, and MoneyLion and was the Deputy Editor of personal finance coverage for Business Insider.

Hi, Reader. I consider myself a pretty seasoned traveler, but I still haven't perfected the art of packing. I usually bring too much, but there are also times I neglect to bring the perfect jacket or going-out outfit that would make my trip considerably more comfortable and enjoyable.

I'm gearing up for a trip that will take me from Los Angeles to Northern California for a mini-festival, then to New York for a Points Path team meeting and San Diego to visit family. With this mix of business and pleasure — not to mention a few different climates — I knew I'd probably overlook some key items. So I turned to Claude for an assist, and it did an incredibly thorough job.

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Laying out the itinerary

I fed Claude a detailed prompt covering each stop on the itinerary, along with my modes of transportation, specific dates, and what I'd be doing at each stop. My partner and I would be driving up to the festival from LA, then I'd be flying to NYC from San Francisco, so I added the caveat that anything that I didn't need for the latter half of the trip could go back in the car without me.

I also pasted in the full details of the festival, since my friends had sent an email with packing recommendations and accommodation details.

Here's the template I used. I filled in every bracket with my own details, so my version was a very lengthy one.

I'm packing for a trip and want a list built around what this specific trip requires, not a generic travel checklist. Here are the details:

TRIP
- Dates: [departure date] to [return date]
- Stops, in order, with nights in each: [city, number of nights]
- What I'm doing in each place: [work meetings, dinners out, hiking, etc.]
- Lodging and laundry access: [hotel, Airbnb with washer, staying with family, etc.]
- Getting around: [rental car, transit, walking, rideshare]

FLIGHTS
- Each flight, with airline and fare class: [route, airline, fare type]
- Elite status or credit card baggage perks I have: [list, or "none"]
- Bags I own, with dimensions: [carry-on, personal item, checked bag]
- My preference: [carry-on only if possible / fine checking a bag]

ME
- How I usually pack: [overpacker, minimalist, always forget chargers, etc.]
- Anything non-negotiable: [specific shoes, camera, work laptop, etc.]

Please do the following, in this order:
1. Weather: For each stop, give typical highs, lows, and rain chances for those dates based on historical averages. Say clearly that these are averages, not a forecast.
2. Bag rules: For each flight, tell me what you believe the carry-on, personal item, and checked bag allowances are for that airline and fare class. Flag the most restrictive leg, since that one sets the limit for the whole trip. Mark every rule as "verify," and tell me the exact page on the airline's site where I should confirm it.
3. Packing list: Build a list organized by category (clothes, shoes, toiletries, tech, documents, extras). For each item, note which stop or activity it's for. Plan outfits to cover multiple stops, and use any laundry access to cut quantities.
4. Bag plan: Tell me whether everything fits within the most restrictive leg's allowance. If it doesn't, tell me what to cut, what to wear on the plane, or whether checking a bag on certain legs makes more sense.
5. Gaps and risks: List anything I'm likely to forget or get wrong on this specific itinerary, such as liquids rules, items that won't work on one carrier, or weather swings between stops.

Don't recommend specific brands or products. If you're unsure about any rule or number, say so instead of guessing.

Claude flagged some itinerary concerns

First of all, Claude rightfully noted that my 4:25 p.m. flight from San Francisco International Airport (SFO) meant leaving the festival by late Sunday morning, before the closing gathering. We'll have to say our goodbyes and hit the road early that day since we have a significant drive ahead of us.

It also flagged that I should book my NYC hotel for the night I fly out, since my flight lands at JFK just before 1 a.m. Not having a place to sleep that night would have been a huge bummer.

...and some bag rules

Both of my flights are on JetBlue, so Claude checked my bag against JetBlue's carry-on limit of 22 x 14 x 9 inches, including wheels and handles.

That's where it caught something I never would have: my Away Bigger Carry-On is listed at 23 x 15.4 x 9.4 inches, over the limit on all three dimensions. I've never had an issue bringing this bag on board and stowing it in the overhead bin, so I still plan to travel with it. But I'm prepared for the possibility that it'll need to be checked — and will pack the essentials in my backpack accordingly.

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It divided my packing list by weather and event

The core strategy Claude recommended was simple: two separate bags. My Away gets packed in LA for New York and San Diego only and never gets opened at the festival, while a festival bag goes home with my partner when he drops me at SFO.

San Diego, where highs typically hover around 70 degrees, didn't add anything to my bag beyond a T-shirt to wear under the layers I'd already have with me. I also love that the packing plan was formatted as a checklist where I can actually tick items off as I go.

The packing list even flagged a few items I definitely would have overlooked, including my Loop Quiet 2 earplugs for the festival and a beanie and scarf for the potentially colder weather across destinations.

One more step to confirm

No forecast is reliable three weeks out, so closer to my departure date, I'll look up the weather for each stop and paste it into the same Claude chat with this follow-up:

Here's the actual forecast for each stop: [paste].

Update the packing list and bag plan based on this, and tell me what changed from the first version.

If the weather changes significantly, my packing list will too.

I'm glad I thought to turn to AI for this task, since I now feel confident that I can fit everything for New York in a carry-on while also bringing the less-necessary but fun extras for the festival like face glitter and a crazy outfit or two. And I can only imagine how useful this prompt will be next time I travel overseas for several weeks.

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Flight School

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Edited by

Sarah Silbert

Sarah is a travel and personal finance journalist who’s written for outlets including Business Insider, Forbes, and Fortune. She’s passionate about uncovering ways to travel better, save money, and enjoy more freedom.

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