Packing for Pack Rats and Pachiderms

I am currently procrastinating. I am fearful of packing for my three day weekend trip to Bermuda. I thought I had it all figured out...a carry on bag and a purse. I would colour co-ordinate my clothing and take only red, white and blue items, just like the British flag. Of course, the clothing pieces would be few, and all would be relatively conservative and multifunctional.

I have always admired people who could go on major vacations with only a small suitcase, so I thought this would be a good opportunity for me to try it. It certainly makes life easier, expedites travel and with some airlines, saves money. 

My friend just announced that she would be taking a "real" suitcase. She had a good argument. Lots of space in case you buy something. You never know what you might need. You don't know for sure whether it will be hot, cold or in between. Everyone else will have to wait for luggage before getting on the hotel bus, so we wouldn't save time.

Now, I'm conflicted. She'll have more "stuff" than me. I might be envious. After all, taking only a carry on bag does not allow for many things which some people deem essential. Corkscrews, scissors, gallon tubs of wrinkle cream, matches, knives, hair cementing products, drinks and spare cannisters of butane are definitely not permitted. On the other hand, they are fine in luggage, although, depending on the uniqueness of the item, there might be the risk of finding a government baggage inspection slip in your suitcase.

At the moment, I have set out 2 pairs of long pants, three jackets, 4 t-shirts, two camisoles, 2 dresses, one navy silk outfit, a bathing suit and wrap, one pair of shorts, two additional pairs of shoes, drugs, undergarments, socks, toiletries, cosmetics, hair products, makeup, camera equipment, a flashlight, money, tickets, passport and a c-pap machine. I wonder if that's enough for 3 days? What if it rains? Should I take an umbrella and raincoat as well?

I believe I've made up my mind. I'll try the carry on for my next overnight adventure. For this particular trip however, I too shall take a "real" suitcase.