The Transportation Board has ALL KINDS of DME threads.
You need to make reservations for DME. It's free, but it's NOT automatic -- you must make reservations. About 2-3 weeks before your trip, you'll receive a DME packet. Included in this packet will be luggage tags, 2 per person. These luggage tags are sticky yellow paper and have your name, the "main" name on the reservation, the reservation number, a barcode, and some other codes. In other words, these are personalized, and are also sticky yellow paper -- there's been some confusion when people received the decorative plastic WDW tags wrongly thinking they were the DME tags. You put a DME tag on each suitcase you will check and will want delivered to your resort room.
OK, it's departure day! Your DME tags are on your suitcases. You check your luggage in for your flight just like any other flight. The airline and airport people at your home airport don't know anything about DME and they don't have to -- DME is accomplished at MCO and NOTHING special is done about DME before then.
You land at MCO. Skip baggage claim! Walk directly to the DME Welcome Center, which is a fancy term for a counter. You check in there, and they tell you which queue to get in for your bus to your resort. Each bus will hold guests staying at up to four different WDW resorts. There is no pre-set grouping of resorts, it's all done on-the-fly on an as-needed basis. You get onto your bus when it's ready (most people only wait in the line a few minutes). You can have your carry-ons stored in the bus cargo bay or take it on with you if it'll fit under your seat or on the overhead shelf. And by the way, don't feel obliged to RUN for your bus. The buses run continually, and it's not like you have a reservation for an exact bus -- in other words, a bus won't be held to wait for you and you won't have to face a bus-full of angry people who've been waiting for you.
The general rule for the drivers is that the reosrt closest to MCO gets dropped off first, etc. When you get off the bus, the driver will get your carry-ons for you if they're under the bus. If the driver handles your bags, he/she deserves a tip. GO check in at the front desk. [It took me 53 minutes from the time I got into the DME line until I arrived at Caribbean Beach Resort. About 30 of those 53 minutes was spent DRIVING; CBR was the first stop. That leaves 23 minutes, and I can't imagine a town car service would be a lot quicker, since you'd have to wait at baggage claim, then wait for the driver to get the car, etc.]
Your bags: At any airport in America, at some point BEFORE baggage claim, the airlines "release" the luggage to the custody of the airport. It's AFTER this point that DME comes into play for lugagge. Employees from a company called, appropriately enough, BAGS Inc. scope out the DME-tagged luggage when it's on its way to baggage claim. They pull all of the DME-tagged bags out of the luggage stream BEFORE the luggage goes out to the public on the baggage claim carousels. This DME-tagged luggage then gets scanned (so that Disney knows its whereabouts) and loaded onto trucks, which then taks the bags to the resorts. The barcodes on the DME tags are reportedly scanned at every step along the way so that Disney knows where they are at all times.
Plan for your bags to arrive in a few hours. You don't have to be present in room resort room to get your bags. They will "magically appear" inside your room if you're not there. It's best to have essential items in your carry-ons to adjust for this delay. It's always a good idea to do this no matter where you fly just in case the AIRLINE delays your luggage. [After we returned from our resort's pool with our kids, we found that our luggage had magically appeared. We packed swimsuits and a whole lotta other stuff in our carry-ons.] If you happen to be in your room when Bell Services delivers your checked luggage, THEY DON'T NEED A TIP. Disney has already "pre-tipped" them.
The day before the end of your vacation, an evil Disney CM will leave DME departure info on your doorknob. You'll have been assigned a bus departure time. It will typically be 2 hours 45 minutes to 3 hours prior to your flight time. This may seem like a lot, but keep in mind that airlines recommend you ARRIVE at the airport 2 hours before your flight. Anyway, you should get to the front of your resort about 15 minutes prior to your bus time. IF YOU ARE FLYING A "PARTICIPATING AIRLINE," you can check your luggage in with the Resort Airline CHeck-In desk at your resort, and you're luggage will be forwarded to your airline for you, and you won't see it again until it's on your home airport's baggage claim carousel. IF YOU ARE
NOT FLYING A "PARTICIPATING AIRLINE," take your luggage to the bus yourself. You can also have Bell Services get it to the lobby for you, but be aware that they are often very busy and you may need to make an appointment or request the service way in advance (an hour? 45 minutes?) of when you'll need it, just to be safe. That doesn't mean YOU have to go an hour in advance, they can store it for you. The driver will load your luggage under the bus.
Anyway, you should catch the bus you're assigned to. Just like on your arrival trip, the bus MAY stop at UP TO a total of 4 resorts, including yours. When you arrive at MCO, the driver will get off first and ask everyone to stay seated. He's unloading all of the luggage. After you get off the bus, get your luggage (and tip the driver if you have luggage) and proceed to your airline's check-in counter just liek you would at any airport in the world. You're now done with DME. You can try to get a skycap or a rental cart to help you with your luggage.
Other notes: If you want to slow yourself down or if you're exceptionally nervous, you have the option of claiming your luggage at baggage claim yourself upon arrival at MCO, and taking it to your DME bus yourself. IF YOU DO THIS, DO NOT PUT THE DME TAGS ON YOUR LUGGAGE.
Also, if for some reason you never receive your tags, don't worry. You can still use the full scope of DME services. When you check in at the DME Welcome Center, just tell them you never received the tags. They'll ask your baggage claim numbers, as well as show you a chart of photos and ask you to identify your luggage. A CM will get your bags at baggage claim for you, they'll be tagged for DME, and then they'll be sent on their merry way without you having to lift a finger.
I hope this all makes sense. If anyone has any further questions I highly recommend you post on the Transportation Forum, as there are many of us who've used and enjoyed DME and we can share our experiences and info with you.
