Ideally, before departing the ship, I would ask them when their current contract expires (most will share the info with you). I also ask if they are on Facebook (not all cast members communicate with guests on Facebook). I find more cast members are willing to communicate via Facebook versus e-mail, as it is easier to access Facebook, and/or change e-mail accounts, while still maintaining privacy. If you did not ask while on the ship, try searching for them on Facebook. Remember, cast members PAY for their internet, have limited free time, and limited access (my server is often online at 2AM Eastern). If you cannot find them online, send them a short letter ... remind them of who you are (include when you sailed, any memorable moments, and a picture, if possible ... remember ... there are THOUSANDS of new guests EVERY WEEK). Ask them if it is okay to contact you via e-mail or Facebook (include your e-mail address and/or Facebook contact). Allow ample time to receive your letter, and respond.
As for shipping ... keep packages small ... under 12" x 12" x 12" +/- should be fine. Do NOT ship any homemade foods, or anything which can spoil. Once packages are received in Lake Buena Vista, they are put in a storage facility, then scanned for security purposes (including sniffer dogs). Accordingly, if you ship something on Tuesday, and it does not arrive in Florida until Thursday or Friday ... it will not pass through security until the next week ... which means it cannot be loaded onto the ship until the following Saturday. I try to send a private message to someone when I am shipping a package. Sometimes it can get to the ship within one week ... sometimes it misses the initial security screening, and takes another week.
Disney Cast Members are NOT permitted to have spirits / hard liquor in their stateroom. They ARE permitted to have wine. I would not suggest sending a 6-pack of beer ... it's not cost effective, and most beer fairly inexpensive. On the other hand, if you know your cast member likes a special wine which might not be available in the Caribbean, or on the ship, it might make a great gift idea. Here's an example:
Cast members from Hungary or Slovakia tell tales of an extremely popular (and not inexpensive) wine (Tokaji). It is not a brand name ... think of how CHAMPAGNE is for bubbling wine in France ... or Bordeaux refers to a wine coming from the Bordeaux region. Tokaji is not served on the ships, and not typically available on the islands. This might make a fabulous gift, especially if your cast member is from Hungary or Slovakia. You'd be surprised at how many items are available in the US, which may remind the cast member of their homeland.
Remember that cast members likely will not have room for souvenirs ... so anything consumable may work best. On the other hand, I recently sent a PM to one of my cast members, telling them I was going to send several t-shirts ... just after they returned to the ship, from vacation. In this example, the cast member will not need to pack as many clothes to board the ship. You would not want them to have to pay an extra $50 (baggage / weight fee) merely to return home with a souvenir t-shirt.
I typically also ask my favorite cast members to let me know when they are returning vacation, and also, to which ship they are returning. When I know a cast member is returning from vacation, I will often ask if they want me to ship anything to them (to the ship) ... ANYTHING they may want from the US. Remember, the retail atmosphere in the US is unlike most European countries ... so do not be surprised if they ask for a pair of jeans (be specific as to size, cut and manufacturer) ... a battery charger for their laptop or netbook (they generally cannot order US-powered chargers to be sent to their home).
When I am visiting New York City, Walt Disney World, or
Disneyland ... if I see something with those locations imprinted ... I try to pick up something for them. I have sent oversized Hershey's chocolate bars from Times Square, "I LOVE NY" t-shirts (mickey-head used in lieu of a HEART.
When you ship something ... I almost always remind them ... if they do not like the taste / do not like the fit ... either give it to someone else on the ship, or throw it away. I *also* ask them to let me know if they like something a lot, and if they would like more (they may feel awkward to ask for gifts ... but they will usually communicate with you when received).
Sending them a hand written note with the gift ... telling them how much they mean to you is ALWAYS a moral booster. It provides a warm feeling to cast members who are working THOUSANDS of miles away from home, and away from their families for extended periods of time.
*** Remember, if you like them enough to send them a gift ... remember to send an e-mail or letter of appreciation to Disney Guest Communications ... referencing the cast members first / last name ... date of sailing, etc. Cast members often receive acknowledgement when a letter is received.
Feel free to shares your story or experiences!
Steven