Oh Goodness, I am sort of obsessed with coupons, lol (and that extreme couponing show). It's always best to print them just before you go as some don't last long and new one's may come up just before you leave.
Just before you go, register at all of the outlet websites, they often have a coupon that you can redeem for a coupon book at the guest services desk at the different outlet centers.
Whenever you first go to a Macy's store, get a Macy's international shoppers card, it gives you 10% off storewide (other than cosmetics and perfumes). You used to get it at the gift wrap area/counter, but you can ask instore where to get it. It last's 30 days and you can use it at all Macy's in the US.
Different stores also have different specials. Register with different websites, like Earl of Sandwich, when you sign up you get a voucher for something free (it was a brownie for us and mmmmm, they have the best brownies).
The website Coupon Cabin has lots of printable coupons. I've had coupons for sunglass hut, gap, banana republic and many more before.
Check different restaurants in the area where you want to go and sign up for their mailing list just before you go, they will often send you coupons for discounts. Denny's is one that will send you a welcome coupon, IHOP usually has coupons. They are often only valid for a couple of weeks (14 days) so join just before you go so that you have long enough to use them.
Also look at the different stores you want to shop at. Like Target, I printed off a heap of coupons for my toothpaste (sensodine), which is $10 here and it was on sale over there and with a coupon I got it for just over $2! So bought heaps of it.
I have joined Landry's club (rainforest cafe, bubba gumps, claim jumper, trex to name a few, they have lots of restaurants). The card is $25 but they add a $25 credit to the card straight away for you to use the next time you dine there (so pays for the card). For every $1 you spend you get a point, when you reach 250 points you get another $25 off your next bill. The card also gives you priority seating.
http://orlandocoupons.com/print-coupons/1509#.UwsMAyiZOg0
http://www.iloveorlando.com/documents/ILoveOrlando_FW13-14_CouponBook-ForWeb-lowres.pdf
There are some good vegas and anaheim coupon websites too.