Rock'n the Road, the guide to your next adventure.
I began this trip as a "reporter" and felt I should dress the part, with both casual and semi-formal clothing, but I soon took on the trip as an adventurer, and wore simple, rugged adventurer's clothing. I washed my laundry every week (or so) and wore some articles for more than one day. Welcome to the life of the homeless, which is what you will be.
If you're traveling with someone and are getting sick of seeing them in that "I'm with Stupid" T-shirt every week, stop at garage sales and thrift stores. Buy clothes for a quarter and have fun, by wearing clothes you would never wear otherwise. Buying your shirts this way could be cheaper than doing laundry, and you'll have different outfits each week. Walk into a garage sale, tell people that you're traveling for months, and offer to trade shirts -- you'll be surprised at their reaction!
Are you tempted to bring along a CD player? It all depends on your situation, but the player, and the dozens of CD's will complicate things. Believe it or not, this brings up an alleged John Steinbeck quote, and he hadn't even heard of CDs. He said something in the way of "we have built a marvelous interstate highway system, which allows us to efficiently cross our beautiful country, from New York to California, without seeing a darned thing." If you're the type of person who likes the stability of putting a CD in the player so you'll know exactly what music you will be listening to, you're a highway person, intent on just getting to your destination (a theme park?) If you enjoy the mystery of scanning the channels, never quite knowing what will pop up, but knowing that somehow it will enrich you, then you're a backroads person, intent on enjoying the journey.
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