On the major highways there are enough Supercharging stations to make any trip worry free and you can plan an A to B trip easily. It gets more complicated when there are no Superchargers like in the Maritime Provinces and States. We made a trip to the East Coast when we first got our 2015 85D and to be safe I booked hotels with charging stations. It was no problem to ask for the charging station to be available for the night of our stay. Admittedly this did slow our travel but we explored many places that would have been a blur if we focused solely on making the fastest time. As contingency I bought a CHAdeMo adapter and used it once at a Nissan dealership where they provided coffee while we charged. High winds reduced our range below a minimum level that I like to have. I now lend my adapter to neighbours with a Tesla making their road trips. It is shareable. Our trip to the East Coast included a few days in Bouctouche NB visiting elderly family in a nursing home. When I called a B&B to make a reservation I promoted the Tesla plan offering a free HPWC for Destination Charging. By the time we made the trip they had installed the HPWC. A road trip with a Model S is not much different than planning a sailboat cruise or small plane trip and I find that enjoyable.