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Miami to Boston

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I've done Miami to NC without a problem. If you haven't done a SC trip yet, my only advice is to try to figure out how much range you will need to get to the next SC and try to get to the next SC with only 20 miles of range left (of less if you're really adventurous). You will spend less time charging this way. Of course if you are at a stop and want to spend more time there eating or shopping, by all means let the car keep charging. The longest leg will be between St. Augustine and Savannah so you will have to charge for a while at St. Augustine. Don't know what to expect once you get past Rocky Mount, NC because I haven't made the trip personally, but I've looked at the route before to go visit NY and you should have no problem getting to Boston.
 
Think about route options with a focus on traffic around DC and NYC. If traffic is backed up between Fredericksburg and Woodbridge, consider 301 after hitting the Glen Allen SC. You have an 85 so can make the jump to Newark without stopping.

Over 4th of July it was fastest for me to go into Manhattan via the Lincoln Tunnel then up the West Side Hwy to HH Pkwy to Cross County Pkwy to Hutch/Merritt rather than fight the GW Bridge traffic. Then you can choose to use the Greenwich chargers and cut over to 95 later or, as mentioned above, take the inland route via 84/90. Good luck with the long drive.
 
You shouldn't have any problem. I drove up to norther Vermont and back in a weekend from NC and one of my co-workers did the same thing to Miami and back from NC over a few days. From NC up to VT you can see my trip report here: http://imgur.com/a/2Ac28

The only advice I can give is just to be aware that Newark, DE is a very busy supercharger and only has 4 stalls so there is a very slight possibility you will have to wait a short time to get a spot. I didn't either way on my trip, but it did hit max capacity (4 of 4 stalls taken) both ways. Also, you may already be aware that superchargers are paired so 1A and 1B share the same 120kw unit, 2A and 2B are paired, and so on. When possible, choose a stall that has both A and B unused to get a dedicated 120kw unit and the fastest charging rate.
 
@Pgiralt thanks for the info. I have done a couple of SC trips, but Saint Augustine is the furthest I have gotten yet. I do try to leave a bit more extra milage so I can drive a bit faster. Not so much a matter of getting there sooner, but driving at 60 MPH on a never ending straight line can be really boring, even on a Tesla.

@LMB (spouse), thanks for the confirmation. Yes, I was originally planning to go straight from Milford inland, but only if I can get a hotel in Boston that allows me to charge overnight, otherwise I guess we'll have to take the scenery route to East Greenwich.

@JohnQ, thanks for the heads up on traffic around DC and NYC. Will keep an eye on that. What you do you normally use for that? Just the Google Maps traffic projection on the screen or do you fire up Waze on your smartphone?

@Zarwin, very interesting, thanks for taking the effort to document it. Will try to do something similar. You hit many of the SC I am planning to visit, so it is great to already have an idea of what they look like, number of places and so on. Good to know about Newark, will try to plan with that in mind.

Thanks again everyone, really helpful.
 
I just use the Google Maps traffic on the big screen rather than Waze and it works fine for me. But I can be a Luddite on occasion.

Regarding Boston hotel, you have an enormous number of charging options. It's amazing how many available chargers there are. Either public parking within easy walking distance of hotels or a few hotels that have on-site charging. I usually stay in the Seaport area for work and park in the LAZ lot bordered by Congress and Boston Wharf Rd, they have 4 slots (free charging, $17 per half day parking). The Seaport Hotel has one night free parking for EVs and at least one charger.
 
JohnQ, good to know that Boston is plentiful with charging options. I will finally be staying at the Lenox, which supposedly also has charging available.

Wow, the Lenox has free charging, news to me (my wife's office was across the street).
Ample EV charging in the Prudential Center garage (perhaps the Lenox uses this)
and the Boston Common garage among others.
The Natick, MA Tesla store has 70A chargers as well, it is about 20 minutes west of Boston.

Have a great ride...