So you've decided to attend your first game convention?
First off, congrats, you should have fun....
Second, I really hope you didn't pick GenCon or Origins for your 1st ever game convention, but if you did I hope it's Origins. Actually both cons are great, don't get me wrong, but they are the big boys and can be overwhelming for a convention newb, with GenCon clearly coming in top for being "too much" as far as cons go.
I'd recommend a smaller, hopefully local game convention. You can support local dealers, maybe find players for future gaming, and definitely find out about other smaller local conventions. A local gaming convention is more likely to be in driving distance and just generally cheaper to attend. You'll have more room to pack stuff and more money to spend should you want to......
....but I'm going to go out on a limb and assume you have to fly to the convention. Why? Well mostly because that's my main experience, but also because flying to a convention is more restrictive and if you go to the bigger conventions odds are you'll be flying unless you like doing a looooong roadtrip.
Right off the bat, once you decide to attend a convention, break out your calendar. Get your registration as soon as you can and note when you can sign up for games and rooms. Neither is as important for smaller cons, but it will be for the larger ones and you might as well get in the habit as rooms for GenCon & Origins and games can fill up in the 1st hour of registration. No, really.......get your calendar, figure out the necessary dates and register for what your want, when you want it. If the convention has an advance schedule, figure out your priority for gaming. Your 1st choices for a game might be full, so having backup plans are good.
When should you arrive to a convention? I recommend you show up the day before and leave the day after if you're flying. If the con is a Thursday to Sunday affair, odds are it'll start up Thursday afternoon and wrap up Sunday by noon. If you can get good flight in Thursday morning and out Sunday afternoon, good on you, BUT....don't forget others will be trying to work that same schedule, you'll have no flexibility if flights have issues (seriously I recommend morning flights before & after con days so you have all day to get there and/or back if there if flights get delayed), and do you really want to try to get in a game right after a spot of travelling and the fun involved with that? Some cons will have an early check-in available and maybe even some early pick-up games.
Once you have your dates figured out, your travel plans in place, and know where you're staying.....oh you don't know that yet? Well I generally recommend staying at the convention hotel for a smaller con and anywhere but as the con gets bigger. The big conventions usually have multiple hotels, but there may be one or more directly connected to the convention space and others a short walk away. It might seem convenient to stay at a convention hotel, but as the convention grows that convenience dwindles. Anyone who has had to wait 20-plus minutes for an elevator at the con hotel realizes that a 5' or 10' walk to their hotel might be preferable....because you might have to wait that long to get back down to the convention as well. Other hotels within walking distance might be cheaper or have better amenities as well.....
OK, so NOW you should have the big-picture travel stuff figured out and you might want to drill-down for the finer details. Does the convention center and/or your hotel have a restaurant......will it be convenient for you to eat there (convenient and affordable) FYI they generally aren't as they are catering to business travelers with company accounts and/or per diem. One con I went to their restaurant was a higher-end Steakhouse. You'll want to figure out your eating options before you arrive on-scene. I generally plan on one a nicer meal out every other day and something else for the rest and avoid room service at all costs (pun intended......room service is usually expensive and decent quality, but meager. $15 for a muffin and orange juice...no thank you). Thankfully these days delivery, including food service delivery, is an easy option. These services will widen your choices considerably.
You might also want to look up your options for grocers/general merchandise near the hotel. It might be well worth your while to walk or take a taxi/uber to the grocery store and stock up on sodas/snacks. Even when flying I tend to pack some easy snacks, maybe a breakfast or two (tops) worth of instant oatmeal, some dried fruit, and a bag of beef jerky. It's good to keep with you in case your travelling goes longer than expected anyway and it can buy you some time when you first get to the con and are trying to get your feet under you. Knowing where you can go to get some OTC medicine or another notebook or some such is comforting at the least.....
You really don't need too much when flying to a con when it comes to clothes and gear. Whatever you'd normally take to a regular game (dice, pencils, notebook, PC sheets, minis, and rules) is just fine. Since I never go anywhere without a computer I keep extra copies of everything where I can access it.....and these days a tablet can go all day, so PDF stuff is a viable option. You shouldn't be working up a huge sweat at a con and since you'll be showering every day at a minimum (you ARE showering every day, right?.......seriously, don't be THAT GUY!) you can probably get more use out of your clothes than you'd think. Fresh underwear for everyday and if you need another shirt, just buy a convention shirt when you get there.....you'll want a souvenir anyway.
Speaking of which, at your 1st con you are going to want to buy stuff. Most vendors, the convention, whatever can take credit cards, so you'll only need cash for little stuff, like food vendors, tipping, vending machines, etc. Odds are you'll be buying stuff at the convention and lugging it home. Two useful things to know, well maybe three. I recommend packing an extra bag in your luggage.....something that can be checked if needed. As long as your extra swag is under 50 pounds and you're willing to pay the extra $25-$50 for an additional checked bag.....just drag that stuff home with you. Stopping by a post office or UPS/FEDEX on the way to the airport is an option, but the hotel probably has a business center where you can go online and arrange for a pickup. Hotels have stuff picked up and dropped off all the time and some of the larger ones are regular FEDEX stops.
One thing I do like to bring with me to a con if I'm flying is a simple art tube. I have one I made from a PVC tube that barely fit into my one bag (which I don't use anymore.....might need to make a new one). I use this specifically to transport any art/posters I pick up from any artists at the con. It really sucks trying to find a tube to protect my expensive art purchase at the con. The hotel won't have any lying around and good luck with that on a Sunday as you're packing up.......you might get one as a shipping tube from that local FEDEX/UPS assuming you planned ahead......
Really the only other things I'd toss out there that if you have a favorite something you need to have, like a certain pencil or notebook....pack an extra one. Go ahead and bring a reusable insulated mug while you're at it. Every con I've been to has ice water easily available and if you need something flavored, those little squeeze bottles of flavoring are just a couple ounces (you can fly with them!). Stay hydrated!
When you get back from your con, do yourself a favor and note what you didn't use/need, what you wish you had brought, and make your own travel list for the next convention.
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The Minotaur for Old-School Essentials
*Requirements:* Minimum STR 9, Minimum CON 9
*Prime Requisite:* STR and CON
*Hit Dice:* 1d10
*Maximum Level:* 8
*Armor:* Leather, including shield...