|The Well-Heeled Traveler
I also hate to check any bags, so if my tenor banjo is the "carry-on", then anything else I take has to either fit inside the banjo case or in a small bag that I can stow under the seat. For this reason, I am obsessed with making sure that my packing is as compact and efficient as possible! Rick Steves watch out, because I can seriously get by with just a banjo case and a very small sling-bag!
For a warm climate like Jamaica or Puerto Rico it's really easy to pack lightly. I'll bring what I'm wearing (including a hat) plus a change of clothes and some swim trunks. And that's it. I'll wear one pair of shoes or sandals without socks. I'll bring a book to read, some printed pages with my itinerary and other notes, and a minimal amount of toiletries. Ready to hop off the plane and go!
For the shirt, I want it to be a cotton/polyester collared shirt - like a golf or polo shirt. This type of shirt is presentable enough to meet the minimum dress code requirements for almost any bar or restaurant that I'd want to go to. I can skip the fine dining restaurants and flashy nightclubs with more strict dress codes. The cotton/polyester blend makes for easy hand washing in the sink or shower, and fairly quick drying with minimal wrinkling. I can wear one while the other is drying.
The same goes for shorts and underwear. For shorts, I prefer nylon shorts with deep front pockets and a zippered or Velcro enclosed back pocket. These kinds of shorts dry quickly and are very comfortable and breezy. For underwear all you need are a couple good pairs of travel underwear, such as the Ex Officio Give-N-Go brand, or Duluth Trading Company's Buck Naked boxer briefs. These you just rinse out and hang overnight. And for footwear, you can't go wrong with all purpose Teva sandals for hiking, wearing in the water or walking around town.
I'll also bring a pair of swim trunks if I anticipate swimming and/or going to the beach. As far as getting by on just two shirts, if you start to feel grungy or repetitive later in the week, then this can be a nice incentive to buy a T-shirt souvenir from that cool bar you drank in all night. Top it all off with the most stylish part of your holiday wardrobe - a sharp looking summertime fedora or similar style hat to both keep the sun off and add a bit of edge to your otherwise drab, touristy, American get-up.
Part of the fun of traveling for me is seeing how minimal I can pack. I once went to Scotland for ten days with just a knapsack no bigger than the typical woman's purse. But now that I'm bringing my banjo along I have extra reason to pack lightly and avoid having to check any bags!