I'm a big fan of road trips. Soon after I got married in 2008 I drove from Monsey, NY to several points in Maine, New Brunswick (Canada), Halifax Nova Scotia, around Cape Breton NS, onward to Prince Edward Island and back to Monsey in about 2 weeks (yes, I drove to an island.... there's an 8 mile long bridge to New Brunswick and a ferry to Nova Scotia). My tripmeter hit 3,000 miles as I crossed the Tappan Zee bridge on my way home.
We booked our hotels for the first week before we left, but once we got to Halifax (where we stayed for Shabbos) we winged every day from then on. We just had travel guides and AAA books in the car and while I drove each morning my wife would call 5 or 10 hotels near where we wanted to stop for the night and get the cheapest deal she could over the phone. Some places cost as little as $39-$59 a night (in July/August) and we got a little local flavor by meeting all these small inn owners. We had no miles or points at the time
We packed 6 frozen chines meals from a local Monsey restaurant (Gan Chai... BDH, you are missed) courtesy of our friend the manager (somebody ordered the food and cancelled after it was already made). We brought a large cooler and a crock pot and so we had chinese food every night for the first week. The rest of the food was mostly brought with us - deli, peanut butter, and other sandwich type foods. We bought a little bit along the way also, though we didnt know much about Canadian hechshers so we were very careful to stick to what we knew.
The most important thing to do before a road trip, in my opinion, is have a trusted mechanic check out every inch of your car and TELL HIM YOU'RE GOING ON A ROAD TRIP so he realizes how much strain you will be putting on the vehicle. I went so far as to buy a liter of oil somewhere in Canada to top off my Corolla mid-trip (I don't recall if it was really needed or not but I know I did it).
