I live in Colorado and recently traveled to Washington, DC for a wedding. This trip took place over land rather than by air. One reason for this was that TSA would have confiscated my present, a locally crafted bottle of liquor, unless checked, which comes with its own risks.
The fastest route there was a straight shot along I-70 passing through eight states until picking up I-270 south in Maryland. For the first few states there was no issue - Kansas was fine with driving through the state transporting the bottle and Missouri's restrictions don't kick in until you have five gallons, over ten times what was in the vehicle. But past St. Louis problems start to come up.
None of the routes suggested by Google Maps would have gotten me there without requiring the commission of multiple crimes and at least one felony along the way. The fastest, most direct route suggested from St. Louis to the hotel would have been by far the most dangerous.
Illinois only allows you to drive through the state with liquor without a license if it is exclusively for personal use. A bottle packaged such that its clearly intended for distribution (which includes gift giving) doesn't qualify.
Indiana is even worse, with the offense ranging from a Class B misdemeanor for bringing it into the state to a Class 6 felony for transporting an alcoholic beverage on a public highway, without the right paperwork, which I didn't have. Even though it was a small amount and it was a gift.
And Ohio assesses a $1k fine for transporting any alcohol in the state that wasn't purchased in the state. Unless you're licensed.
The closest legal route adds about 2.5 hours to the fastest drive, making it about 22% farther.
In order to continue legally a detour south through Kentucky, which does not restrict small imports of alcohol except through dry counties, was required. West Virginia also allows unrestricted transport of under 10 gallons of alcohol so long as it is not for resale, so this was a more viable route given my cargo.
Things get tricky again in Maryland, which very well might have seized the vehicle and slapped me with a $10,000 fine or even jail time if I was found to be hauling this bottle without a license. I could have argued that I was exempt as a "consumer", but that would been a job for a lawyer in a court room some time later, after missing the wedding.
Thankfully, Virginia looks more kindly upon those in my situation. Anyone bringing less than a gallon into the state not for resale is exempt from the crime of illegal importation. No reason to drive a gauntlet just to save a few minutes.
Seems like a small price to pay to not risk having my car seized and being arrested for any number of misdemeanors or even felonies, but not knowing how strict some state's alcohol transport laws are completely removes the choice altogether. It doesn't even come up for consideration. Thankfully there were legal routes available but there might not have been had the trip started elsewhere.
An ounce of prevention is worth a pound of cure. Knowing the law and acting accordingly can prevent a lot of unnecessary pain down the line.