Consider going on a Disney Cruise.
I've been blessed to have been twice.
The first time for my honeymoon and then 2 years later with my in-laws (we got a great deal).
My first Cruise
The first time I went I was still pretty new to the gluten free diet. I didn't do any planning ahead of time, but it didn't matter. The Disney Crew (what they call the staff on the ship) was very accommodating. The second time I went I let them know ahead of time that I was on a special diet and then I mentioned it again to my waiter the first night.
Everything was wonderful!
Not only was everyone extremely helpful in showing me what did and did not contain gluten at the buffet (they recommend not doing the buffet because of contamination issues from other passengers, but I insisted), but they also made food specially gluten free just for me! They made special sauces and pancakes that were delicious and there was a plate full of hot gluten free rolls for me at each dinner!
Second cruise. See how happy I am at dinner?
And when my husband ordered a sandwich for me (through the free room service) he asked that it have no bread because I can't have gluten (the way we usually order my food). They brought me a sandwich made from gluten free bread!!!
I should have asked them what products and/or recipes they were using because everything was so good (and we all know that not all gluten free products are even worth putting in our mouth)!
I could go on and on about it, but I'll just let you read this article about another couples experience on a Disney Cruise (found in the Celiac Central Newsletter). They even met with the executive chef of their cruise and learned some interesting facts:
P.S. Everything else about the cruise was fun too ;).