My DH (just celebrated 2 years this week at WDW!) proposed to me on one of the beaches at the Caribbean Beach Resort where we were staying. We laugh about it all the time, because it is the ONLY time he has ever been romantic! J/K! He trys! He proposed as we were walking back to our room the night that we checked into the resort for our stay. It was very beautiful and romantic!
While we were at Epcot this week, We were walking from Test Track into the gift shop (back entrance), and there were some very secluded, quiet benches without anyone around. DH said "There is a good proposing place! I am sure the magic happens there all the time."
We visited DH's sister (who is a castmember) who told us the most romantic proposal at Disney story. Proposer and his proposee (and some friends) were eating a lovely dinner at the Cali. grill when at the end of the meal, proposer went to "use the bathroom". Well, everyone was waiting around for a bit and wondering where he had gone. They finally decided that they would go downstairs to wait for him. There a castmember said "are you so and so, please come with me" They followed the cm to Cinderella's Horse Drawn Carriage, which took them into the MK. There proposer was waiting for proposee in the Prince Charming costume at the front of Cindy's Castle. I may not have told the story completely correct, but when my SIL told me the story, it brought tears to my eyes!
Good luck to your DS and his future fiancee!
Korey