I think it's Onset to PTown, PTown to Marblehead, Marblehead to New Castle, New Castle to Boothbay, and BoothBay to Camden/Rockport/Rockland. That's 4 days up and 4 days back. If you're going to SW Harbor from Camden, it's two days there and two days back.

If you're going to enjoy Maine, I'd do what others have suggested: I'd make on the hops a longish one to MDI from either PTown or Jamestown.

There's a group that I've used to source sailors to join me on the passage portion - OPO. The usual situation is you have them as guests on the passages (you take care of the food and consumables as you would for most guests); and, they pay their transportation from the start and finish ports.

With your boat, I'd have you plus three and go from Onset to MDI in two days. Then I'd have your bride meet you in MDI with your kids. Spend a day together using the one-way rental car and see that GREAT ISLAND, provision the boat, etc. Then I'd spend a week or two touring Penobscot Bay and environs. Then you can head to Boothsbay from the Rockland-Rockport-Camden area. From there, without WEATHER, you make the hops down the coast. It's one long day to New Castle. After that, it's shorter hops.

A total of three weeks would be good first trip.

Provisioning at MDI (with a loaner or rental car) is great. You can pick-up a bit here and there along the way. Camden, if you stay at Wayfarer is easy with their loaner cars to provision with. Wentworth at New Castle has a similar marina with loaner cars and great places to provision if you stay. Those places are not inexpensive.

In between, you can either take moorings, anchor, or take slips. With the kids, spouse, and pet. I wouldn't underestimate the value of allowing some decompression that being able to "step ashore" and "wander around".

If it's just you and your spouse, then that still is important -- but depending on your frame of mind, not as essential.

EXCEPT for the fog, cold water, lobster pots, and rocks -- there is no nicer cruising location than Maine on the eastcoast. You really want to enjoy those areas and be flexible with the weather and your crews' emotional needs. If you push it in the fog and rain -- you'll completely change the experience.