I'm walking Chicago docks On weekends. Help!!

[Snowbyrd]

Morning all sailors. I am a crazy minded, foolish, young and big dreaming hopeful. With that being said I WILL make my dreams come true so I am going to start from square one.
Well here is a short story of my plan so noone gets bored reading this.
I spent a few years of my life when I was younger, in the U.S.V.I. I want to go back and plan on getting there around October. I want to live on a sailboat and spend my days enjoying what I find makes me happy and making money when I need it. I see myself from right now till I leave on this type of path
-meet sailors by roaming docks and networking online.
- build my knowledge and skills by paying for lessons and offering my skills to those I have met.
-spend time while I'm at marinas looking at boats, get a feel for how I feel in them, find what I like and dislike, and most importantly, gain knowledge from those that know so much more than I do

I've been looking for boats for a month now, just to get a feel for what I'm getting Into and plan on purchasing just before I leave or when I get there. There is no chance for failure because I choose to tackle obstacles in my way. I know not everything will work perfect or easy but I'm willing to do everything it takes to make this happen.
Anybody that can give me hints on what docks in Chicago area are best for my type of approach, I would appreciate it
Anyone that simply wants my help in trade for knowledge I would also be willing to do so. I want to 'get my foot in the port'
And I actually am a normal person haha. Most think I'm crazy for choosing to do what I'm doing, but I feel it is who I am. I love sleeping in hammocks, climbing trees for my food, and spending time enjoying the free things in life. I also HATE being cold.
Thnaks in advance and my appologies for my layout of my rant. I'm bad a putting things on paper in proper order and to top it off I'm stuck doing this on my iPhone.

[sawingknots]

not to worry windy city,life is short and not always just or kind,i've been to chicago you have reason to rant,good luck and fair winds

[Snowbyrd]

Thank you. I've had suprisingly high approval by everyone I have shared my plans with. That is... Everyone but my grandparents. They are still stuck in the 'earn a living' trend that I see nowadays not being the same as it was in yesteryear. I do believe in working hard, but for me, I want to retire while I am young enough to enjoy it, then work while I'm not able to go have fun As I am older. But I don't think this world will be the same in 20 years. The way we are heading, I am gonna be better off than most. We shall see....

[HPLou]

Good luck in your pursuit of a sailing life. Your wanderings around the Chicago docks should include some visits to the local yacht clubs on race days/evenings where you have a chance to be picked up for crew (rail meat). It's a good way to learn some basics as well as meeting alot of sailors. A great life style if you can live it. Good luck and enjoy the journey.

[Snowbyrd]

^ I see there are approx. 4 or more marinas in chicago vicinity( not including surrounding towns). Is anyone familiar with any of them? I guess I am gonna have to visit each one.. Parking and entrance to the marinas if I recall is limited to patrons of the marina. Is there a way around that? I guess I will just use trial and error. Thanks for all the replies everyone. To me, I feel completely lost as I walk up to a marina as I have no past memory of how things flow there. Owell. Gotta start somewhere right.

[sidney777]

If you can get there go to Crowleys Yacht yard at 95th street and Chicago river. Right near state of Indiana and not the street. They have donated sailboats for sale on land and probably you can go inside the sailboats.
.....While you are there you can go to other boatyards (not marinas) and look at boats.

[Snowbyrd]

Wonderful!! I google mapped it so I shall go there very soon. I am interested in possibly buying a repo sailboat also, but it's hard to search for propper auctions and know if they are a scam or not. I can hopefully find a reliable source for marine auctions.

[sailortjk1]

Your right unfortunately for you, most of the docks in the Chicago area are secured as are the parking lots. This makes walking the docks a bit difficult. You can get close to the boats but not on the docks in most cases. The harbor with the easiest access is Monroe. The boats are all on moorings cans but many hang out in the North wall area. You can gain access to a lot of friendly boaters right there. The North wall is exactly that, the very North end of Monroe harbor between Columbia and Chicago yacht clubs. speaking of yacht clubs, most of the racers hang out in the clubs. Columbia being one of the prime ones. I believe they have a skipjack program that places crews with boats but you would have to inquire further with the club. Good luck to you.

[Snowbyrd]

Well I spent all day walking through the marinas and talking to who I could. One gentleman gave me his contact and also gave me good info which further sharpened what others have said in this thread. I do see Columbia yacht club as most likely what I will hanging around and I found the 'north wall'. I see good future happenings based on what I have found. Jackson harbor is also closer to home and the people there are friendly as could be. I see they have a low key but well set up breakfast buffet and traffic (boat and car) is low but still enough to meet plenty of fellow sailors. I'm excited about this and if anyone in Chicago wants free assistants on anything I'll trade my skills and back muscles for your knowledge. I listen well and would love someone to talk to me about everything they know. Most importantly I would like to get a good feeling of being on a boat. Good night sail net.