So… you will be organizing a poker run. Fun, fun, fun!!
I have been on many poker runs (power boating) in the Great Lakes, St. Lawrence river, and the Miami to Key West run. Lots of fun, but there sure must have been some organizational skills and the work of many people involved to pull them off. The runs I have been on were usually 2-3 day events, and we paid the registration fees up front, usually months in advance. Be sure to look into insurance/liability issues, as getting an event insured may be expensive.
From the perspective of a participant, I can tell you that being uber-organized and communicating what will happen at each stage of the event are key. Having a few designated ‘point people’ who are responsible for various aspects is important so that when the participants have questions, they know who to go to. Usually a packet of information is given upon registration (picked up the the evening before or on the morning of the event) and all the organizers wear easily identifiable badges. Generally there is a mandatory meeting the morning of the event and it gathers everyone together to go over the schedule of events and expectations. At this meeting (usually during a provided breakfast) everyone gets to meet, the rules are given, and there is a sense of excitement generated.
During the run, having “chaperones” available for the slower boats was helpful as once everyone takes off in a staggered start (spread length and width-wise), sometimes on certain legs, navigating can be a bit tricky on unfamiliar waters, so the chaperones were able to troll around and make sure we all knew where we were going- not an easy task at some of the speeds we were travelling! Often a boat moored at an important navigation area that required a turn was helpful.
At each card stop, picking up the card was easy as the cards were in large envelopes and easy to grab when extended on a long pole to reach across the gap between the boats.
What was especially nice was that at the breakfast, lunch, and dinner gatherings, the food was substantial and plentiful. Boaters (or I imagine snowmobilers, for that matter) are a hungry lot. Playing hard sure works up an appetite, and the catering folks that were hired knew how to feed a crowd and we never felt worried that there would not be enough for seconds as they made sure there was plenty for all. Make sure the food and drinks (non-alcoholic) are plentiful- the focus was on safety, so no drinking and driving (or flying, in your case!) were tolerated. Maybe you can arrange to have the airport (depending on size) cater the meal, or they may allow a private caterer come to the airfield and set up a tent for the meals.
For the final dinner (usually on the second day) there was a HUGE meal and tons of prizes. Maybe some of the suppliers for the sport can be contacted to donate items such as caps, jackets, shirts, as well as useful items to have that are pertinent to the sport (emergency flare kit, etc.). Usually the local marinas got in on the act and donated something. It was nice to have so many ‘door prizes’ as we were a large group, and ouside of the big prizes for the winning hands, it gave nearly everyone a chance to win something. There was also usually the “Hard Luck” award for the person who blew an engine or had a disaster of expensive proportions!! So, having lots of prizes is nice- they can easily be obtained- just ask as you may find the sponsors and suppliers to be generous- it is free advertising for them!
When the cards are posted, make sure the board is big and that each hand is labelled as to who is the owner- it was great fun seeing who had what cards and then, of course, the last cards were set out towards the end of the final dinner. The grand prizes were quite large- sometimes a cash prize (several thousand dollars), or more modest (entry fees to the run for the following year). Sometimes a local sales/repair/detail shop would offer a prize for services or goods.
It seemed the best prize was the bragging rights, though!! Include a good PA system so everyone can hear what is going on and a personable MC is always fun!
Have fun with the research and planning- leave no detail un-covered and be sure to involve those that will be working with you as it is a huge responsibility and if shared, it can make your life easier. Make sure to include contingency plans in case of bad weather as the event can still be held but it just might have to be modified.