Sailing Clubs
If you are starting very fresh, you need to get together a quarum of like minded folks who wish to start a sailing club. These plank members can draw up a purpose of the club. It might be to promote sailing in general, racing, cruising, lessons, etc. Write up a statement with your intent or what the direction of the club will be.You should figure out a fee to charge for joining and this will depend on what your expenses are. Write up a budget. You can file with the IRS as a non-profit organization and you can obtain insurance through U.S. Sailing (which will be apart of your costs). You need to find a name to call your organization. If you will have some of your club racing, then you can get some info and a PHRF handicap book from U.S. Sailing. If you just intend to have cruises, then you might not need the insurance coverage as each member can provide their own. Then you should have a social event to invite people to. You can start with bulletins at local marinas or call or mail the announcement of a new sailing club and an invite. If you hire someone to create a meal for this party, then charge a fee to cover your costs. A pig roast might be a good idea at some marina site. Or a restaurant. I may have seen that you are from Canada in which you would have to find a source for insurance and deal with whatever non-profit status that is available. Generally the volunteers do not get paid. If they get paid, then they are not volunteers. If you have a race management guy or team, then usually they are paid to cover their costs (fuel and insurance). Some clubs, if they are both cruise and race oriented will have a general membership fee which covers the general costs including cruising and then an additional race fee to cover the expenses of racing (that way cruisers who do not race won't pay for something they don't do). It is always a good idea to have fun races now and then, or race/cruise events where all members can participate and these events will be open to anyone (not just paid race fee members). That way you might be able to get some cruisers into the sport of racing (if that is your intent). Eventually you might wish to have a board of directors and draw up some by laws and maybe even incorporate so that there is no liability to the board members if something goes wrong. By Laws are something that might only be changed by a vote of the general membership and the general membership should approve the by laws from the git go. That way you get a lot of input from various people so that you arrive at something tolerable and effective.
There can be procedures on finding people for the board each year and you will have the likes of a Commodore, vice commodore, rear commodore (the commodore from the previous year), secretary, and treasurer. Then you will have committee members such as race chair, rating chair, program chair, cruise chair who have voting rights (a quarum - usually 5). Each chairman can have more people on each of their committees if they need them. Meetings can be monthly and you follow the Roberts Rules of Order. It would be a good idea to have a newsletter and a web site. Find a person or two to take those tasks on and they should be present at all meetings as at least ex-officio officers of the club if not official.
As far as events are concerned, you can have a spring event (or dinner) and a fall event (or dinner). The fall event can be to pass out trophies from racing, if you race. During the summer have various cruises (if you are somewhere where you can cruise) and have food at your destinations, if possible, on land. All cruising boats can raft in a star raft so each boat looks like a pedal of a daisy. That provides a nice swimming area in the middle. You can create various parties or have Friday night fun races (for all members) with a party at the end. You can have a party at the end of each series race or regatta. You can have a spring, summer and fall series, with say 5 or so races in each series with one race being a throw out. Check racing rules for management, rules and scoring procedures.
Sailors usually like parties, so there is no limit as to ideas for parties. Individual boats might sponsor a party after a fun race, for example, and they can attach a theme to that party. I don't know what your facilities are, but if you are all in a marina, you can have a progressive dock party. You can play volley ball or other games. Have treasure hunts for kids (don't forget the kids), fishing contests, dinghy races - get creative.
You can always find a local sailmaker to give a speech at a dinner or a seminar on sail trim, material, etc. It depends on how rich your club is and then you can hire guest speakers at events. You can have a CPR seminar. On and on and on. Good luck and have fun (the initial requirement).
can now Motor Sail from Lake Ontario to Georgian Bay! The nerve of some people, eh!?!