For those that drive from Massachusetts...

We used to make it a three day/two night drive as I don't like driving after dark. Bout 10 hours the first day and stay around or just south of Richmond, VA. 8 hours the second day and stay at Pooler, GA. Bout 5 or 6 hours the third day to WDW.
 
IF I were to do it, that would be my plan too. 10 hours in a car is way more than enough!
 
We drive down once year from SE MA. We used to stop in NC overnight. Now we drive straight thru. My DH drives thru the night and I take over in the morning.
It’s hard to tell exactly how long it takes we’ve done it in as little as 18- 21 hours overnight. The 2 day trip takes a little more time bc of traffic.
There’s a great thread on the transportation board called for 2,000 mile round drivers. There are lots of helpful people with great driving tips.
Good luck!!

Edit to add: when we do 2 days we left by 3-4am
Straight thru leave by 7 pm
 

We did it once, straight through. Not in any rush to do it again, unless there comes a time where we’re retired and not on a schedule, etc. Then we might try it again but take our time and break it up. I agree it is nice to have your own car. We even took our dog on that trip!

Issues we had were hitting a lot of construction delays, even in the middle of the night (not sure if those are as big an issue today), and massive 18 wheelers that were literally inches from our car in the pouring rain on a lot of the busier sections of the highway. Pretty intimidating, even for us Boston drivers, lol.

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I also had good intentions about driving but had trouble staying awake enough to drive safely during the night. And I couldn’t sleep when anyone else was driving, either, too worried they’d doze off. So not a great experience. I don’t really like to fly, either, so I’m kind of stuck either way, but flying overall is a lot easier and more peaceful for me.
 
I am not sure where in MA you are. I am in CT near Hartford. We drove once. We left around 2 am to get through NYC and northern NJ before rush hour. We also hoped the kids would sleep, spoiler they didn’t. We stopped for breakfast in mid NJ then really tried to push through (one more bathroom and gas stop planned but due to delays we had to stop 3 times) to SC where we spent the night. We opted to go around DC to avoid traffic. We hit a ton of construction and didn’t get to our hotel until 9pm. We had hoped to be there by dinner.

We slept for a few hours and got back on the road at 6am. It should have taken us about 6 hours getting us there around lunchtime. We again hit a lot of construction and didn’t get there until 4.

We were all so exhausted and the kids were hating each other by then. We did nothing that day or the next because everyone needed to rest.

I would not do it again. We lost the first two days of the trip and the last two days everyone started getting anxious for the trip back and kid fighting started up again.
 
I am not sure where in MA you are. I am in CT near Hartford. We drove once. We left around 2 am to get through NYC and northern NJ before rush hour.

I also live in CT and have driven to the southeast many times, and I'll give a tip: it doesn't matter where in MA you are, you cannot transit the NYC-DC corridor without running into rush hour at some point unless you avoid the area entirely (which I often do). Driving from the I-91, I-84, or I-95 entry from Massachusetts into Connecticut all the way to anywhere on WDW property is approximately 21-23 hours behind the wheel, and you'll need at least four 15 minute stops for fuel (just a gas and go by the time you've decelerated, fueled, and re-accelerated onto the highway adds 12 minutes). It's 24 hours of driving.

If OP wants their car there with their stuff, which isn't unreasonable, they should drive to Lorton, VA. Leave at 3:30-ish AM, get into Lorton, they load your car and drive the rest of the way for you, so the next morning you arrive, actually refreshed. https://www.amtrak.com/auto-train
 
I also live in CT and have driven to the southeast many times, and I'll give a tip: it doesn't matter where in MA you are, you cannot transit the NYC-DC corridor without running into rush hour at some point unless you avoid the area entirely (which I often do). Driving from the I-91, I-84, or I-95 entry from Massachusetts into Connecticut all the way to anywhere on WDW property is approximately 21-23 hours behind the wheel, and you'll need at least four 15 minute stops for fuel (just a gas and go by the time you've decelerated, fueled, and re-accelerated onto the highway adds 12 minutes). It's 24 hours of driving.

If OP wants their car there with their stuff, which isn't unreasonable, they should drive to Lorton, VA. Leave at 3:30-ish AM, get into Lorton, they load your car and drive the rest of the way for you, so the next morning you arrive, actually refreshed. https://www.amtrak.com/auto-train
We have friends who do this regularly. It works for them. I would like to do it, but if we want to take our dog, it’s a no go, as no dogs allowed on the auto train (or so I’ve read). Just one other thing for us to consider. Dog aside, when I’ve priced it up before, often flying is cheaper.
 
We have friends who do this regularly. It works for them. I would like to do it, but if we want to take our dog, it’s a no go, as no dogs allowed on the auto train (or so I’ve read). Just one other thing for us to consider. Dog aside, when I’ve priced it up before, often flying is cheaper.
If all you care about is money, it's about a wash - once I calculate in my entire cost in vehicle wear and tear (I calculate that as my purchase price divided by my expected 200,000 mile vehicle service life, $0.30/mile or so), tires, fuel, and oil changes, and a hotel stop, it's about $1,000 each way. That comes down to about $250 to get to Lorton for me, so $750 difference - coincidentally about the cost for two people in an Amtrak roomette on most dates, plus I save an entire vacation day each way, and my sanity.

Though either way, bringing your car only really makes sense when you need your car down there for an extended period, or need a ton of luggage (I'm an AA ExPlat and Amtrak has huge baggage allowances, so this is a very high bar). For a typical family of 4, it's almost always the same price or cheaper to fly and then rent or taxi when required.

For taking a dog, driving over 3 days is about the only way, and that's assuming the dog can handle 3 days with limited breaks - ours top out at 2 with 30-ish minute park visits twice a day to let them get some energy out, but that's a Labrador and a Newfoundland (previously two Labs). This puts the range limit at about Jacksonville for us, though we just hire a pet sitter or have friends or family stay with the dogs instead 95% of the time: pro tip, Newfoundlands don't like Florida at all, the only one I've heard of happy with the weather there is in Peter Pan's Flight (though he'd love visiting Fairbanks in January...)
 
We have driven from NH a few times, driving allowed us to pack anything we wanted, it saved our family so much money, no flights, no rental car, etc. We drive straight thru, 2 drivers alternating shifts. Takes us about 25 hours, we leave around 3pm, and arrive about 4pm at resort check in time. The hubby takes first 6 hour shift, then I take over and back and forth with bathroom and food breaks. In Connecticut we continue on 84 to Scranton Pennsylvania then down to DC, completely avoiding NJ and NYC traffic, its very smooth and easy. Now its just the two of us so we fly...
 












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