The NY Times had an article a few months back about flight attendant Heather Poole and her ability to fit 10 days of clothing in her carry-on suitcase. Intrigued, Christine and I attempted the same packing technique and were successfully able to enjoy our 7-day trip to Puerto Rico without paying to check our bags! I'll be utilizing Heather Poole's packing system once again during my road trip to fit more than 2 weeks of clothes between a carry-on size suitcase and a medium size duffle-bag.
Check out the NY Times article: "10 Days in a Carry-On". It's a short read and an easy technique you can use on your next trip!
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