Drive VS. Fly from MD... with a Twist

I drove down with my 17yo and 10yo last December and it was the best vacation I have ever taken hands down. We got to stop places and see things that we have never seen before. We didn't limit ourselves to Disney either. Having our own vehicle and no constraints on flight times felt so freeing! We always fly and this was our first time driving. If your 2yo is a good traveler I vote for the drive. You can always fly later! This sounds like the perfect time to take advantage of driving
 
We started driving when my daughter was 5 weeks old and have driven probably 20 times since then (she is now 16). An earlier poster mentioned taking things to distract the kids, and I found that crayons (triangular shaped ones that don't roll off the tray), color wonder markers and paper, those mats they draw on with a pen that you refill with water, movies, etc., can keep them distracted for a couple of hours at a time so you can eat up some miles. Good luck, be safe and have fun! Disney is magical anytime, but especially with a younger child!
Boy this took me back! Our first two were born in '89 and '91 and we made lots of long road trips, also starting when the first was just a baby. I remember stocking up on a bunch of toys and books from the Dollar Tree. If they each kept a kid distracted for 20 mins on the way down and 20 mins again on the way home, they were well worth $1 and I didn't mind chucking them when we got home. When hand-held video games and portable DVD players became affordable it was a life-saver!!
 
Boy this took me back! Our first two were born in '89 and '91 and we made lots of long road trips, also starting when the first was just a baby. I remember stocking up on a bunch of toys and books from the Dollar Tree. If they each kept a kid distracted for 20 mins on the way down and 20 mins again on the way home, they were well worth $1 and I didn't mind chucking them when we got home. When hand-held video games and portable DVD players became affordable it was a life-saver!!
mine were a little older than yours as 79 and 83 but we did same. worst trip anywhere was a red eye flight when oldest was a toddler and decided not to sleep. mine always did better driving and still do as we are on the grandkids now
 
If your son won't wear a mask for the flight, you really aren't going to have much option but to drive. But you will still have a larger issue when you arrive at Disney...if he's not going to wear a mask, how are you going to enter rides and shows?
 
When are you going? I fly out of BWI, too and the 2 hour flight vs. 14 hours in the car....... We did the drive once when we just had one toddler and it was ok - we arrived exhausted though (stopped for the night in SC) and our toddler cried/fussed most of the 2nd day in the car. We now have 3 kids and always fly- I can handle 2 hours but now way would I do the drive, everyone would arrive miserable. We went last Dec and my 2 year old wore her mask just fine - we told her she had to wear it to go see mickey.
 

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