Maine Island Trail in sections…
I would also like to start paddling sections of the MIT. With our 2 year old I can no longer get away for more than 4-5 days at a time, and even that's pushing it, but hopefully enough to start getting a bay or two in every season. I'm not a big fan of point to point paddling, instead prefer paddling closer to shore and checking out scenery as I go, although might just have to island hop given the layout of the bays and points. MITA isn't true wilderness paddling, lots of commercial and boat traffic and private residents out on the islands, but it is serious exposed ocean paddling. The points also make things trickier as points tend to do. But it's convenient for me as a flatlander without the luxury of being able to travel days to get really out there.
I've paddled out of the Stonington area a bit, great place to start getting a feel for Maine paddling, while having the resources of Old Quarry Campgrounds to steer you in the right direction. Lots of options out of Old Quarry, from close in and protected to a circumnavigation of the exposed Isle Au Haut, although can get a little busy on the islands mid summer. I also get the impression Old Quarry has the ability to pick you up off an island if things don't go well, which is always a nice option to have in your back pocket. Don't mind paying a bit more to park my car there knowing I'm supporting a choice group of folks, also nice to be able to take a shower before driving back to the flatlands. Would be a great spot to base camp and day paddle as well. http://www.oldquarry.com/
The online app I'd use for at home planning, wouldn't want to rely on it out on the islands where reception can be spotty, always opt to get a copy of the MITA handbook and drag it out along with charts of the area. Good to do a bit of homework and mark off the available island campsites and major compass bearings so you don't have to deal with those things on the water in case a campsite is being used or the fog rolls in.