Well, I just got back from my online group's weekend and we had a blast! I'll tell you what we did and how we planned it to maybe give you guys some ideas.
1. We listed several locations and each person was told to indicate which locations they could attend. The location with the most votes was chosen...this year it was Chicago. (actually the suburbs, but basically Chicago.)
2. We get group rates through
www.hotelplanner.com and a link is placed on the message board so that everyone can just click and reserve.
3. A sign-up thread is created so that people can sign up to bring food, drinks and equipment as needed.
4. Friday night we have a "meet n greet" in a conference room we reserve at the hotel. Nothing special is planned; people just generally sit around and get to know eachother and usually the night-owls will take off for some fun and adventure.
5. Saturday morning: we go to breakfast together at a predetermined place. Poor restaurant...LOL!
6. Saturday daytime: we have a picnic at a place that has been reserved in advance. This year (and last year too) we had someone bring volleyball stuff and people brought chips, dip, desserts, grills for barbequeing and people made hamburgers, bratwursts, jerked shrimp, Italian beef, ribs, etc. Also, lots of ice and sodas and "grown-up drinks".
7. Saturday night is usually a pre-planned outing. Last year we went to a Rennaisance-themed dinner theatre and this year we went to Game Works. We got a discount on our game cards since we were a large group.
8. Sunday morning: breakfast at a buffet. It's easy since everyone pays before they eat, so there's no complicated figuring out who owes what.
Anyway, I hope you guys manage to do this. I had SO much fun both last year and this, and I know you will too!