Going south/ Key West bound

Dylan Christopher

Dylan Christopher

New member
Hi All,

Planning to head south for the winter. Frosty Burlington is just not a good spot come January. Thinking of heading down to New Orleans or Austin, TX and thumbing my way across and down to Key West, FL. I'm pretty new to the road so I'm wondering if anyone has as advice for me in the ways of travel and how to go about finding cheap or free housing. I'm a painter so I plan to sell my paintings and other pieces of art along the way for travel and food money. Has anyone been through a similar route? I'm mostly interested in Key West, where to stay, etc. Any and all info for a rookie looking to get on to the better things in life would be extremely helpful. Cheers!
 
key west is a mixed bag, its a really nice place to visit if you have money, but busking requires a permit thats 100 bucks if i remember correctly, and even then you have a lot of competition to deal with. as far as selling paintings on the street i would assume youd also need a permit and locals are quick to spot a non native and call the law on you and get you harassed.

as for a place to stay its pretty expensive to get a hotel there and sleeping out on the beach is a sure way to end up in county lock up. key west sounds really ideal to alot of people but the sad truth is its a pretty big yuppie place with not the friendliest people if you dont have money. its a huge tourist spot making it a real hassle to get away with not having money. a buddy of mine got pinched shop lifting from a publix down there and in less then 10 minutes the cops were there and had him in cuffs, it was all buisness as usual for them, the cops were surprisingly decent to us and told us hed most likely be out in a day or two. a few days later we met him at the jail and got the fuck out of key west. i dont recall the name of the bus system that we used to get from miami to the keys but it was very cheap and actually not a bad way to get down there, we met some other traveling kids on the bus and thats when we found out about the permits and what not. although if i remember correctly (i was drinking a lot those days) there is no open container law in one or more of the keys. so if yer a drinker its nice to know you can walk around drinking and for the most part not get hassled.
 
Thanks for the heads up brother. I had a feeling it might be some touristy trap. I'm thinking St. Augustine, FL. Really just looking for a place to go to get out of the cold for the winter that's relatively safe, has an artist community, and isn't overly expensive
 
unfortunetly the days of florida being a safe haven for travelers has long since gone. st augustine is just about as bad if not worse then the keys. its the oldest city in north america making it a even bigger tourist trap then the keys. police there are awful, and its extremly expensive due to it being a tourist town. granted its absolutly gorgous, but still...i wouldnt want to spend a whole winter there without having a place to sleep safe every night thats not outside.
 
like i said, florida is pretty non traveller friendly in general, theres a few cities that tolerate it but for the most part its a real bad place to look homeless. i grew up there a few years after iggy scam and remember looking for the great places he wrote about and even then they were gone. ide say florida is one big gentrified place and should be avoided unless you have family or friends to put you up while you are there.
 
Yeah I'm in south Florida right now and don't really recommend it. I think it's worth coming through and visiting once....and then you never have to come back, haha. You'd have a good time in Nola and I hear from friends that Austin is awesome. That being said, if you ever find yourself in Miami, don't hesitate to contact me:) I can show you some cool art spots, some cool bars, and the anarchist culture down here if you're into that
 
florida definately has an art scene if you go down there try to blend in. surprisingly enough i had the least amount of problems in miami the cops there were pretty chill and had somewhat of a rep with the homeless. everywhere else florida wasnt so friendly and not just the cops. st auggie was alright but the locals hated me thus the police but its a nice place to stop in. theres a bus that goes there from jax.
 
Catching a flight down to Miami Wednesday the 13th which is tomorrow, I think I have a couch set up but still unsure past those few days. I'm really not amped about Florida but it's warm which is okay by me. Anything worth knowing about down there? Squats, art communities, places to dumpster dive?
 
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