You have a couple of issues here.

The first is weather. In January you can have snow the entire way on some of the obvious routes, and, if your luck is bad, ice, which is even worse. The I-84/I-81/I-40/I-30 route, which is shortest, takes you near and across mountains for much of the way. There are no scary cliffs on any of these mountains, but it snows at higher elevations when it only rains down below. And that is your worry.

The second is driving time. By the shortest route, this is 2 1/2 days of driving EACH WAY. That gives you one day in Dallas and one day in three other places if you take the whole nine days off. If you bag the mountains for I-95/I-85/I-20 to avoid snow, you still have the possibility of ice and it is 3 full days of driving each way. If you really want to avoid snow by taking I-95/I-10, it adds another half day of driving each way -- 7 days of driving on a 9 day trip, then back to work the next morning.

If you really want to do this and are sure of your weather, take I-81/I-40/I-30 out and I-20/I-85/I-95 back, which will take you through Richmond on the way back to NE.

A little snow? What, me worry? The problem is that once you get below New Jersey, they have no clue what to do about snow (I live in New England but have lived in VA, NC, TN, and MS). I could tell tales that would chill your bones, but I will spare you.

Think really hard before taking this trip at this time.

Some general thoughts. Under the best of circumstances, driving 9-10 hours/day or more - this trip takes 6 days of pure driving, without sightseeing on those days in January the northern half of this trip could find you in bad weather, slowing the trip. Not sure your 7-9 days allows for much sightseeing.

There really is not an efficient alternative to I81 thru Pennsylvania and south - for about 500 miles. I have driven that road thru most of VA. I share a fear of highway precipices and unguarded switchbacks, but did not exerience that on this road. Mind-numbing boredom and lots of big scary trucks and a lack of highway services of any kind - but not cliffs. In January, you have short hours of daylight, and considering your driving fears, this will further limit hours/day on road and lengthen the days of this trip.

I can speak more specifically about the northern portion of the trip. Mapquest says it is about 10 hours Richmond to Boston - that is almot always impossible, except in the middle of the night or if you are extremely lucky. Most mapping programs take you over the George Washington Bridge for some reason. Do not take these routes. Following your past practice of entering cities into GPS and going from there, you want to set Danbury, CT as your first city - this will get you away from GW Bridge (Mass Pike to I84 to Tappan Zee Bridge, ending at NYThruway to I81 - a map will make sense of this).

From Richmond north, timing is important. You have to try to avoid rush hours in Balt/DC, NY metro area, and then Boston area. Best way to do this is to leave really early - like 4 AM. Or if you are OK driving at night, around 9/10 AM. I drive several times/year Boston-DC area and have never made the trip in less than 9 hours, sometimes as long as 14 - there is always some issue in NJ.

You may have to choose between taking more time off from work - or skipping the sightseeing.

Ackislander and I were posting at the same time - combine that response and mine and you get the picture. Summarized - you are being unrealistic.

Agree that you are being unrealistic in terms of time it will take you to do this trip in Jan given short days and lots of potential for bad weather and consequent slow speeds and extra days on the ground.

Separately, I kno wyou are in love with your GPS - but you really need to get a set of decent maps for a trip like this. That way you can plan a whole trip in advance - and reroute if necessary based on weather - without being hostage to a machine operating with very limited information.

We do many road trips- although mostly in europe - and always map out the trip in advance and have good detailed maps that are helpful if we encounter 1) construction detours, 2) accident, 3) bad weather or 4) for some other reason want to make a route change. We tried a GPS that came with the rental car once and it was terminally stupid and essentially useless.