As a guy who was in your shoes a few years back on board a Disney ship I may be able to help offer an idea. My wife and I started dating back in 1996. In 2000 we started to think about going on a
Disney cruise, which is when we decided to book a cruise in Dec. of 2001.
My plan started to take place when we started to think about getting married. We started to look for rings around Feb of 2001. We went to a few different places and would point out what she wanted and I started to get ideas. My whole plan was to get the ring before we went on our cruise and propose to her on the Disney cruise ship.
The most nerve-racking time I had was actually traveling with the ring. The day before the cruise a co-worker of mind talked me into getting insurance put on the ring in case it was lost or stolen during the trip. God forbid if that ever happened, I would not of been able to afford replacing a 6000+ ring. So a tip to you, Call and insure the ring before you go!!
I decided to place the ring inside of my suit packing during all the traveling. That was the hardest part having to check my suit bag at the airport, the hotel, and then finally the cruise. We went on vacation to Orlando of 10 days prior to the cruise. So every few days I would just check to make sure it was there.
Finally on board I had to come up with a plan to actually do the proposal. Let me tell you how nervous I was! After the first night, we were both puking or guts out. First time being on a cruise ship sort of got to us. We had waves between 30 and 40 foot so that boat was rocking and rolling. My wife went back to the room and fell asleep for the night around 9:00 PM. I felt that since I paid so much money for this trip I was going to make it worth it.
I decided to go down and talk to the head person over our dining room (wife remembers his name, I can't). I asked him if there was anything special that could be done. He said ABSOLUTLY!! So we planned on doing something the 2nd night during dinner at Triton's.
The next day came and I wasn't having the greatest vacation up till this point because I am nervous as heck. As the hours kept ticking by I was thinking about what was going to happen.
Once we got back on the ship from doing that day's activities my wife jumped into the shower. By this time it was about 6:00 PM. I grabbed the ring from the suit jacket and ran to Tritons. I found the head person and gave him the ring. He told me not to worry about a thing that he would take care of everything at dinner while they are doing desserts. The only request I had for him was to have a ship photographer their to capture the moment for us.
To say the least I went back up to my room (she was still in shower) and couldn't believe what I am getting my self into. I am usually a very shy person and I was about to have everyone in that dining rooms eyes on me.
Once we headed down to dinner and found our table, we started talking to the people we were assigned to eat with. We didn't see them the first night because they ate at Palo's. In getting conversations rolling they asked how long we were married and I quickly got really nervous about the question for some reason (as I think you understand). As the dinner progressed they asked everyone at the table what they wanted for dessert. When they were bringing it out they brought the dessert for myself and my tablemates. The head person came over and told my wife that they had a "special" dessert for her.
She started to get really freaked out about them clearing all the glasses of the table and she seen a photographer standing about 20 feet away. She never caught on thinking it was just part of the "show" they put on for their guests.
Then we saw a big people tram coming from the kitchen with the head person in the front holding this silver platter up high. They headed all the way to our table and put this platter in front of her. He reached over and took the lid of the platter to reveal this model of the Disney ship made out of chocolate. She is starting to think, Ok, this is cheesy. Then the waiter guy said open it up. She had to look at it harder and she noticed that it had a lid on it. She opened it up and they had it full of M&M's and the diamond ring sitting in the middle. She immediately got teary eyed and I grabbed the ring from the Chocolate Wonder and got down on my knee and proposed to her. All this time the photographer is snapping pictures. Can you believe it that she said yes? Everyone in the entire Triton's started to clap and I felt that I had 100 ton of bricks lifted off of my shoulders.
The other couple we sat with both were crying and said that "we had made their vacation" even though they didn't even know us.
The rest of the cruise we were known as the couple that just got engaged. We had VIP status. Anytime a CM seen us standing in line for a picture of a character they would come over and rush us to the front of the line. Everyone who recognized us would say congratulations. It really made the trip that much special.
To make an extremely long story short listen up. Propose to her early on in the cruise and propose to her on the ship. The CM's really went above and beyond my expectation.
Terry