I flew with the engagement ring in a small box and it worked out fine...I could always feel the box in my pocket so I knew it was there. I even had a moment of panic in the security line at DCA thinking that it would go off so I slipped it into my shoes that were going through the X-Ray machine and slipped it back into my pocket...probably needlessly but I wasn't taking any chances! The "I need to use the men's room, why don't you go through security" would probably have been easier but didn't occur to me at the time.

I also had to lock the ring up in the hotel safe since I was waiting a day to propose and Mrs. East Coast Wing likes to use the safe in the room for her wallet and jewelry...I wasn’t comfortable just having it hidden in my suitcase so you may want to consider doing that. Ironically, during dinner the night I proposed she asked me how I got the ring to Key West without her seeing...I thought for sure she had seen me take it out of my shoe at the airport or scampering down to the front desk but apparently not!

Good luck and congratulations!