I would suggest that you spend two weeks instead of two nights. We have more places to sail and anchor than you have time for. I have been sailing the Maine coast for over thirty years and there are still places I have not been to.
Seriously though, you must plan for things to go more slowly than you think they will. Southwest Harbor is a fine place to charter and sailing up Somes Sound with an incoming tide is great. Note: watch out for strong winds that are possible coming down off the mountains in the area of Valley Cove. The head
of Somes Sound is a fine place for the night, either in the cove by the town landing at Somesville or in the northeast corner by the boatyard and the lobster resturant. They have rental morings. Valley cove is ok if you get a mooring but is really deep for anchoring
The Cranberry islands are good for the night unless there is a northern component to the wind
. Little Cranberry has a nice resturant on the pier but in the summer you need reservations at least a day ahead.
Seal Harbor is rolly for a night and it is full of private moorings so anchoring
is difficult. You need to be a member
or guest to get a yacht club mooring.
Northeast Harbor is the best yacht harbor in the area. Call the Northeast Harbor mooring agent on channel 9 for a mooring reservation. Great harbor, shops and resturants, acess to the Island Explorer bus system, showers, fuel
, everything that folks on a boat might need.
My advice is to skip Bar Harbor. It is a long sail up Frenchman's Bay and overnighting in Bar Harbor is rolly.
Good luck and give a holler if you need more info.