J.C.
Awww . . . what a sweet tradition to carry on!
We have done quite a bit of travel with our kids. Family is in Michigan, and so is the family summer place. I found that driving trips with a newborn (we took our first trip with my first son for a wedding when he was just a few weeks old) took forever because we had to stop and nurse so often. If you have a hand pump or power adapter for the car, bring that so that you don't have to stop quite so many times. I always sat in the back of the car when the babies were really young to keep the baby company, read books, sing songs, etc.
Once you arrive, make sure you bring all the things baby likes at home. I always took a nursing pillow and my own bed pillows - much easier to get comfortable on strange furniture. If you can bring whatever the baby sleeps in now, that seemed to work best (my second son slept in an Amby baby hammock, which was the best for travel - he slept just like at home.)
Also, especially if you have lots of family there or the walls are thin, you might consider a white noise machine that you can take along when you travel, just to block out the noises of an unfamiliar place.
Last thing - my kids seem to always get sick when we travel, so make sure to pack baby tylenol and bring your pediatrician's phone number just in case.