I would say drive vs fly. I have not flown with my boys and my reasoning is because flying you have to stay on a very specific schedule. So if he has any issues with it and your flights are only 30mins apart you don't have time to stop and do whatever he needs you too. Flying for me can even be stressful when our flights are close because of that rushed are we going to make it feeling and also if we wait in the airport for a long time that can get old too. Flying a lot of lil ones have troubles with their ears not popping and if he cries you will all be stressed. If you drive and he cries you can pull over or not feel so guilty about letting him cry when you know he just needs to go to sleep because there won't be anyone else to hear him.
We start out early and plan for delays. A quick 10min stop for you 2 will now take minimum 30mins! We've gone to Washington DC and Colorado both were long trips. DC we didn't allow enough free no drive time and we didn't allow the extra time for driving either. CO was much more relaxing because if the drive is 13hrs plan on it taking 18. If you make it there early GREAT! Also
don't make any big plans arrival day because you will be tired and he will be very tired but also anxious. Use that day to get settled in your room and let him get familiar with it, I'm not saying spend the whole day in your room but do spend some time in there before you expect him to go to sleep. I would suggest any place you could go on nature walks and stuff. You 2 can get some peaceful time together and Rylan will love being outside looking at all the stuff around him. I don't really know exactly where though.
I make a list of things I need to pack for the kids a week or so before we need to pack that way I can go over it and have plenty of time to add and remove things. Also, pack snacks if he is eating cheerios or something like that and some books and fav toys. Pack the used sheets and blankets from his bed that way when you put him to bed at the hotel or whatever it will still smell like home. If he falls asleep to music or something don't forget to bring it. All of this is just ideas, it's stuff that's made it easier for us but every family is different so I am of course just offering it as a could use tip. Also, we have 2 playpens/travel beds whatever you want to call them so if you don’t have one you are more than welcome to borrow ours.
Whatever you do don’t over plan and just have fun spending quality time together as a family! No mater what you do you will remember it because it will be your first family trip 