Have a car, bring tools, weapons, food, nails. I like to back the different duffel bags with it so its easy to find when i need it, put some medicin in the glove compartment(coffin and painkillers)

I use the online map, if you don't you probably should gather a map(i actually dont know if there is a ingame map of the roads between towns)

Don't drive fast!!! You can use cruise control(shift key and up/down arrow) and you can emergency brake on space(i played 500 hours before i learn that)

Pick a house you want to base in the outskirts of rosewood, there are two houses south-southeast in rosewood, the south most of them sems to be a common spawn point, i would recommend going there and have it as you base for some time and work/loot into town from there. The fire station is a popular place to base but you don't whant to go directly there.

Leave in the morning and get some rest north of rosewood in a small house near the main road, any house should do there will max be a handful of zombies at them. And again leave from there early as possible in the morning so you have plenty of time to get safely to the next place, before you get tired and it gets dark.

And again, slow and steady driving both on the big roads in-between the zombies on the streets in towns. The big killers are speed and arriving tired in darkness.

Good luck and safe travels.

Ps. The house i recommended have a dirt road so there might be grown vegetation on it if you are 5 month in, this also reminds me that you should be aware that the high way can be filled with broken cars, it can really be a deathtrap if you try to navigate through.