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We haven't been on a trip with Frankie get. We are going to the beach for a week in Aug. It will be about a 4 hour drive, I'm a little nervous about the drive, it will be the longest car ride he's been on.
We've taken M on 2 vacations to florida, and one weekend trip that was a 7 hour drive... She did wonderful on the first trip to florida where it was just DH, myself, and her... Slept the entire plane ride, and even slept through just about all of our dinners in her stroller at Disney-lol.... The 2nd trip wasn't as good, but it was with a ton of family and her schedule was all mixed up, and there were older kids who kept her up... The weekend getaway was just this past weekend and she also did great... The key is to drive( or try and fly) during their normal sleeping hours.... We left at 7 on a Friday night, and got in late night and she slept the entire time.....
We went to Va at the beginning of June (6 hr drive). Christie slept most of the drive since we scheduled it during a time I knew she would nap. While there she charmed everyone at the wedding and behaved like a perfect angel.
Traveling is getting harder as he's older and more aware of his surroundings. He does great when awake, but doesn't want to sleep unless it's with me. Also, he doesn't like long car rides. My MIL lives far enough away that he'll only sleep half the ride so we have to plan a break for him to play if we're not both in the car.
We took our daughter to the Virgin Islands (5 hour plane ride from Chicago) in March when she was a little over 4 months old, and she did great. She didn't mind the plane ride at all and loved the resort, pool, etc.