In the past I always came back from Florida with no weight gain or something loss, except one year I had the dining plan: dessert every meal! That is the main reason I don't like the dining plan.
When we last went with free DDP (in 2012), we made a conscious effort not to overeat, as we had done on our previous free DDP visit in 2010!!
DW and myself did have quite a few shared CS lunches rather than one each, plus we tended to ask for fruit instead of fries and a fruit cup or bottle of water for dessert - most places were happy to oblige. We also cut down on the buffet meals as the temptation is always to overeat there - I think we only visited Boma and Crystal Palace, and managed to restrain ourselves.
TBH, we aren't big on exercising at home, so perhaps it was the 7-10 miles a day walking in the parks that meant DW lost 3 lbs, and I didn't gain (or lose!!) any weight.
The free DDP was a great part of our holiday. I lost weight before I went to WDW and gained about 5lbs over the two weeks. I didn't want to diet or feel deprived when we were on holiday, so I ate what I fancied.
I bought a fitbit one at best buy for my last trip (landed back Saturday). Highest day was 9 miles at Seaworld. We walked from Rosen Plaza through convention centre. Most days were around 5.5 - 6 miles. Started to get obsessive checking steps and making sure I hit target competing against DH. Complaining well you did more as you got to walk around Walmart. Haha.
Always put on weight. There's that moment at MCO when I put back on my travel clothes. Whoops one or 100 too many cookies. Life's for living which is what I won't be doing when Jillian Michaels starts screaming at me again through the TV next week!!!
Now the strange thing is, I always lose weight when I go on a cruise! I think the sight of all that food just puts me off eating, and there is always so much to do that I am more active than I think I will be!
I haven't been to WDW yet but I have always lost weight on our trips to DLP. When there we tend to eat a lot more than we do at home including desserts with most meals but we also do a lot of walking which we just don't do at home.