I am a "newbie"--probably one of the newest! I just started this hobby about 7 weeks ago, but a lot of the "pros" are either on their way to Florida or already there!! Everybody on this site is very friendly and helpful though, so you have chosen the right place to start!
If you go to WDW not knowing that you want to trade, the only way to start is to start buying pins off the "racks", and they run from $6.50 -$15.00, although more fall in the $6.50-$8.50 range. They also sell a few "starter sets", like one that has 4 pins on it, each representing one of the parks, and it costs $15 I believe (we bought several of these) so you end up with 4 pins at an average cost of $3.75 each, and you can trade these one for one for a pin on a cast member's lanyard--usually a rack pin-so you're trading a $3.75 pin for a $6.50 pin. There are also lanyards with pins already on them, and as I recall baseball caps with pins on them. And, there is an AK starter set that has 5 pins on it for $18. If you want pins with you already when you go down to trade with Cast members you have a couple of options. There is a site called "cheappins.com" that sells pins fairly cheaply-they range from about $2.75 to maybe $7 or $8, but most are under $5. The catch is, most of these pins (not all) are pins that are good just to start your own collection, or to trade with Cast Members; most of them are not pins that "advanced collectors" (for lack of a better word) are going to want to trade for. But they are a very good way for you to start a supply to trade with at the park with CMs. CMs wear lanyards around their necks while working with pins that are stocked by Disney--so they are usually rack pins that are for sale at the time in the park; and you will see a lot of those pins from the sets, because that's what people trade with! The pin selection is better in the morning as they start their day, and gets a little "weaker" through the day as people trade. Also, try to look for "cast Managers"--usually a shirt and tie is the giveaway--if they are wearing a lanyard a lot of times their pins are just a little nicer than regular CMs--and you
might find a treasure. Not always, but sometimes. You can also start checking out e-bay. Be careful here! It is overwhelming the number of pins you will find!! And it is very tempting! But
if you watch carefully, you can find pins for under $5. You will find certain sellers that sell pins from Germany; they are cute, and they are "cheaper" and as long as they are stamped "disney" which most of them are, they are tradeable. But, these are the pins that are not really wanted by most "regular" traders; BUT they are good to start with for the CMs
As for where to trade; obviously the cast members are anywhere and everywhere. If they have a lanyard on they are trading. There are trading rules of etiquette that you will read about but of course since they are working, you let them finish a transaction or whatever, and then ask if you can see their lanyard or trade. There are also "pin stations" throughout all the parks where pins are sold--some big, some small--you will usually find more "knowledgeable" CMs there, sometimes there are "pin books" as well to look through to trade; and at some of the bigger ones (like Epcot) you will find "civilian" traders. You will also find a big trading center at the big
Disney store at the Disney Marketplace, where a lot of people congregate to trade. If you are new, this can be very overwhelming! I did a lot of asking questions, and a lot of looking, and almost no trading--and I mean what trading I did was basically very nice people who made a trade because they knew I was "new" and did it to be nice and helpful. There are many very nice people who will share with you, and help teach you, and there are a few who are in it for money, or are just really aggressive, or are what are known as "sharks". If you do try to trade, don't do any trade that doesn't feel right; all reputable traders understand a friendly decline.
Sorry, there is so much to explain--and this is just the beginning! Have fun with it--it can really enhance the experience of your trip--it's like a great big treasure hunt! It's a lot of fun, and you will meet some wonderful people, and may even make some lasting friendships. Hope this helps!
Sorry again for being sooooo long!
