“O, Sunlight! The most precious gold to be found on Earth.”
Something I've learned from my limited seasonal work experience is that it's never too early to start planning for the next jump. Positions like mine have pretty solid start and end dates so it's kind of like putting a puzzle together; you find another job whose start date is close to your current job's end date and try to make them fit. Because I hate being unprepared and scrambling for a last minute job (though that's often what I end up doing) I started my winter job hunt as soon as I began at Yukon River Camp.
The goal, as I've mentioned, is to go south in the winter and north in the summer thereby always being at a fairly comfortable temperature and avoiding both the southern heat and northern snow. Unfortunately for me most of the winter jobs in the US are at ski resorts. They hire huge numbers of employees for the season but not only do I not particularly like being super cold, I also don't have a ability to pack or store large amounts of warm winter clothes.
With ski resorts out I began looking at places like Steamboat Wells in Death Valley California. They offer housing and a meal plan plus a decent hourly wage, but they, like Yukon River, are in the middle of nowhere. While a summer of social and cultural seclusion is relaxing, a sort of vacation, I'm not sure I'm up for nearly a full year of isolation. Next!
Realizing my need for at least visual stimuli (the social part I can usually do without) I began thinking about the Florida Keys, maybe doing some waitressing or working on a boat for the winter, and I started Goggling hostels I could stay at. By pure chance the Google map showed a little dot way off to the south east in Puerto Rico where there is a little hostel that's bright and cheery and very vacation spot looking. So I emailed them, just like I did with The Marquette House in New Orleans, and they they have agreed to let me come down from about November through March. In exchange for 5 hours each day five days each week I'll get a bed in a dorm, $20 daily bar credit, and $50 per week which is enough for me to buy rice, beans, and maybe the occasional chocolate bar.
Now it's time to do some research. I'm sorry to say that most of what I know about Puerto Rico comes from West Side Story, which I'm not sure was the most accurate portrayal even in the sixties.