Are you far from Milford? I would suggest just starting with a range charge at your home.
Newark, DE
Glen Allen, VA
Rocky Mount, NC (our usual stop using ICE cars at the end of Day 1)
I've done a bunch of long trips (overnight) and the temptation is to stop at/near a supercharger overnight. This presents two problems. Unless the SC is near the hotel, you need to go SC either when you arrive (and you're tired, it's late, you want to get dinner), or you have to charge in the morning, which will delay you getting back on the road. You might be able to charge during dinner or breakfast, but then you're stuck with what's within walking distance of the SC. Now at Rocky Mount, you're lucky because there is one restaurant (Texas Steakhouse) and a one or two hotels. But that means leaving your car at the SC plugged in, and you have to schedule/time when to start charging to be full when leaving in the AM. I had this problem at Cranberry Twp, PA -- I booked a hotel which I thought was close, but it wasn't nearly as close as I thought. So even though the SC was at a hotel, that hotel was twice as expensive as the one I booked. So I had to sit and charge and wait.
What I've done a few times now heading south is stop overnight between two SCs (for instance, Lumberton, NC between Santee and Rocky Mount) -- there's a hotel and food right off the highway.
Lumberton, NC
Santee, SC
Savannah, GA
Lake City, FL or Saint Augustine, FL
Looks good to me.
Also, A while back I ran into a spreadsheet that could be used to estimate your time at a supercharger, based
upon arrival SOC, ending desired SOC, Model S type I think it was called Tesla Supercharge Time Calculator and a member on TMC crafted it under the username MATTEO.... Ok I just found the link to the Google Spreadsheet.... you can import it into your Mac, PC or iPad... Here is the link ---->
Tesla Supercharge Time Calculator - Google Sheets
I got my car in March '14, and my first road trip was from Greenwich to Dayton, OH (before there was a SC there, BTW). Anyway, I spent hours and hours and hours creating such a detailed spreadsheet tracking driving energy usage, SC arrival time, SOC, recharge time, SC departure time, etc.. down to the minute. It was a really great plan taking everything into account (using EVTripplanner mostly for the estimates of each leg). Well, my plan flew out the window about 6 hours into the trip. I'm sure you'll find the same thing. I've done several long trips since then, and it's just a seat of the pants thing now.. I look at how far I have to go to the next SC, multiply that by about 1.25 to get my base SOC needed. Charge to that amount (or likely more) and then get on my way. No planning needed. No fretting about range anxiety. If energy was getting a little low, I'd slow down to bring it back into the "drive as fast as I want" range.
Here's a pic of my first (and only) "planning spreadsheet". I laugh now going back and looking at it! I'm sure you'll do something like this on your first long road trip.. but I'm sure you'll realize that it's not really needed! Just get in the car and go!!!
And side note: It was a spreadsheet just like this I created to track the "actual" which was the inspiration to create
SuperCharger Trip Logger so I could just key in a few values at each stop, and let the computer figure out the rest.