Dearest hive mind,

My girlfriend and myself plan to go on a bicycle trip without a particular destination. The first direction will be somewhere in south Florida in order to escape the cold. After (and if) we'll arrive we will decide on our next course of action.
Our plan to cover 30-60 miles a day. Carrying the bare essentials in order to curb our weight.

Issues:

- Winter. We plan to leave after our lease is up in the end of October. Meaning that we are going to be out there in the midst of the cold. Florida hopefully will provide some warmth but till we get there its going to be chilly.

- Money. We think we might save about 750$ each, and we assume our biggest cost is going to be food. The money will drain fairly quickly and we are looking for some creative on-the-road-money-making ideas.

*** Some ideas we bounced around are:

-Posting/Looking for gigs on Craigslist. As general labor, landscape services, whatever we can get. It might work but I think that the smaller towns don't have their own Craigslist section, or have insufficient interest and demand.

-Day labor centers. Could also work but again, a lot of the smaller towns lack any type of day labor centers.
Standing with a sign with something like "Strong back, hard labor, no handouts". The police might harass us. Anyone tried that?

-Places to stay. We will try to reduce any shelter costs to minimum. We do not plan using motels frequently.

- Camping in random forests, camping sites, state parks and such.

- Wwoofing. We are both very interested in organic farming and would love to check out and work in some farms.

- Couch surfing. On a limited capacity. We don't really want to exploit this system for free lodging but want to hand select a few interesting folks to host us.





So, dear folks,

Any comments or nuggets of wisdom regarding the issues above?

What kind of gear would you take with you? Sleeping bags, small tent, versatile stove, warm clothes, bicycle fixing tools, food. What else?

Any words of caution? Did you try it and gave up after a week? Things you would do differently? Success and failure stories?

Any forums, books about the subject, online resources?

Thank you in advance and have a fantastic day!
My cousin has been to Chicago a couple of times before, has seen Cubs, Sox, and Bears games, has eaten pizza, has been to most of the museums, has spent plenty of time in and around the Mag Mile, has been to the Goat...basically he's already done everything I would take a visitor to do. This is his first time in Chicago without any parents.

I'm going to let them run the show, but I'd like to supply them with some good ideas. Is there anything going on those days that we should check out? I never get to see my cousin alone, so I'm not really sure what he's into. He's recently taken up (electric) guitar and is into "urban streetwear" (he designed a brand a couple years ago and sold a bunch of shirts with his logo), if that helps. Even though he's 18 now I'm not sure if the other two are yet, so please keep that in mind. I'm not going to let them do anything illegal. (Sorry.)

I need ideas for dinner on Tuesday, something to do that night, and things to do on Wednesday morning and afternoon. They'll probably leave around 5pm on Wednesday. (They'll be staying at my place, so cheap hotels/camping recommendations aren't needed.) We'll have access to a car (obviously) and transit, so anywhere in the city is good.

Thanks!