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I had a separate suitcase filled with wedding only stuff and just packed my OOT bags in there. My destination wedding was in Hawaii and I figured the extra bag charge of $25 is cheaper than shipping it out there ahead of time. I also didn't want to fill up my wedding planner's house with my wedding stuff.
we're putting our OOT bags when we arrive at the destination. we figured it would be easier to do it that way...then again we only have to put together 20 bags.
Random question, but what are you putting in the bags? I'm doing OOT bags as well, and I was thinking
1. A map of the area with points of interest
2. Bottles of water
3. Candy
I need some ideas!
Here's what I put in my canvas totes:
Macadamia nuts
Beach Towel or Beach mat
Maps
Welcome Letter with Schedule of Events and Invitation to the Day after Brunch
Trail mix
Water
Luggage Tag that acted as name tag to differentiate the bags
Travel size sunscreen
Check out http://wiki.weddingbee.com/Out-of-Town_bag for more ideas as well.
For some reason, I love hearing about what you ladies are including in your OOT bags!! 
I think regardless of where/when your wedding is, bottles of water and a travel sunscreen are two universal items to have! Maybe also mini bottles of scentless lotion and liquid hand soap would be nice, too. (I hate those little bars of soap that hotels provide!) I will definitely be including these items in my OOT bags along with other local goodies that I come across in the next few months. (Sorry, LittleBear, I'm a bit off topic...)
No prob Carly! I love where this is going! This was a topic of conversation last night and everytime I read about it, I add more things to my list, like the soap idea (I too am not a "bar" soap kinda girl!)
Here's what we have on the list thus far:
Water, map of island, island magazine with ideas of things to do, sunscreen, lip balm, gum, salt water taffy, salt & vinegar chips, gold fish, swedish fish (catch the beach theme..?), welcome note including itinerary and important numbers, cd (nothing elaborate), post card, ferry schedule, and a hangover kit including Advil, bloody mary mix and saltines.
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I am making OOT bags for everyone who comes to our destination wedding (we live in Chicago, wedding is on an island in North Carolina). I'm just not sure how to get them there! I've thought about shipping them but I think it would be very expensive! How are you planning on getting your OOT bags to your wedding location?