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Re: Advice request: traveling for the first time
Phase 1: Check school travel policies regarding transportation. You're looking for information about adults (number, ratio, and qualifications) and transportation methods (i.e., does the school require some particular method for some particular distance). There may also be rooming requirements (I'll get to some of those later).
Work with the school now, they might even help fill out the budget a bit. Do NOT violate school policies--they really don't like that for some reason.
Phase 2: Figure out where you're going. This would pretty much be asking the team "where do we want to travel and who do we want to play?".
Phase 3: Make preliminary arrangements. That is, register for the regional and start hotel/transportation shopping. At this point, you'll need to figure out how many students you can take without violating a school requirement--and how you determine who goes if you have to leave someone behind. Start figuring out payment/fundraising.
And now for some other tips:
--Hotel breakfast is usually a really good thing to have. But look into what that breakfast is: if it's just donuts and coffee, you're going to have a lot of hungry teenagers. (Or hyper teenagers. Whichever is worse...)
--Do some advance research into venue food--it may be worth getting something delivered (or picked up) for the team.
--Speaking of food: Dinner should be planned out somewhat ahead of time. Either have a place to go eat or return to the hotel for pizza.
--If anybody doesn't have contact info for the lead mentor/other key leaders, they need to get it.
--Make sure that everybody is aware of team travel policies like buddy system, curfew, and the like.
--Just to make things easier on the leaders: make sure everybody wears a team shirt on travel days. Much easier to figure out who is in your group and stick together--and if you're missing someone, they should be easy to spot.
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Past teams:
2003-2007: FRC0330 BeachBots
2008: FRC1135 Shmoebotics
2012: FRC4046 Schroedinger's Dragons
"Rockets are tricky..."--Elon Musk

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