Over time, you will feel more comfortable with travel. In the end, it is good to feel like you can handle disaster and be ok. Last summer, I went on two weeks of travel overseas and had all my insulin frozen. It turned out ok. I don't trust hotel fridges, they can freeze too easily. I just use a frio as discussed by others.
It is always good to test before driving and test every hour or two if you don't have confidence in your blood sugar control.
If there is a sudden alien attack on the drive up and take all your diabetes supples, you can still go right to Walmart and replace everything. There is a Walmart in Quincy and one in Lynn.
I am driving to Boston over Labor day and back. I like to stop at Cracker Barrel for a meal on the way.