Lot's of good
advice already, I'll throw in my $.02. We
haul out in Boston and summer at a marina in
Portland so this year we did an overnight from Boston to Portland. We timed it so that by the time we got to southern Maine it would start to get light and we'd be able to see the lobster trap buoys. Well, the winds were better than expected so got there an hour or so early and had to use the searchlight to keep track of the (very few) buoys we saw. Now there are lots of buoys even well past the 3 mi. line in hundreds of feet of
water.
I would advise that you start your Maine
cruise in Portland and make your way 'Downeast'. Reason is the prevailing winds are from the S to SW so it's usually an easy sail heading up the coast. When you're done you could then just shoot straight down to Gloucester or Provincetown (tacking all the way
)
If you can get your hands on a copy of the Cruising Guide to the Maine Coast do it. It shows up as
sold out at their website and Amazon unfortunately.
I'll give you a few of my favorite stops along the way from Portland.
North of Sebasco Harbor is The Basin. Tricky to get into and can be crowded on weekend but beautiful.
Anchored just north of Malaga Is. near the northern tip of Bear Is. You can walk around Malaga. Has a sad
history.
Seguin Island about 20 mi. east. Only if the
wind is < 10kn and from the S to WNW. NW to SE winds will make it uncomfortable. There are 5 moorings available (plus a USCG mooring). The two inner moorings are best for 30' or less IMHO but I just moored on one of them (35', 5' draft) and with a -1.2' low tide I made sure to pull in the mooring line as it slacked up with the low tide.
You can land on the beach about 2 hrs either side of high tide through low tide. Take a tour of the lighthouse (if keepers are there).
Easy trip up to Five Islands where there are 3 or 4 rental moorings from FIYC. They are marked with FIYC and have a stick with a jar for a donation. Lobster and rolls from the shack at the
dock.
Motor through Townsend Gut and the swing bridge to get to Boothbay Harbor.
Boothbay Harbor has lots of moorings for around $40-$50/night.
Round Pond on Muscongus Bay. Several guest moorings for around $35/night. If full then anchor north side of Ram Island. Also northwest side of Hog Island there are Audubon moorings (donation requested). On the way east from here check out Eastern Egg Rock for puffins.
Anchor on the north side of Hupper Is. by Blubber Is. Short
dinghy ride to Port Clyde. Small general store. They have
fuel as well at their float.
Rockland, lots of places to anchor but I've stayed at Safe harbor marina there.
Hurricane Is. on west side of Vinalhaven. Moorings and great hike around the quarry. Didn't stay overnight so not sure if it's rolly.
Anchored off NE side of McGlathery Is. Lobster
boats at 4:30AM(it's Maine).
Nice hike through the island.
Anchored between Devil Is. and Bold Is.
Stayed in Southwest Harbor at a marina but also anchored in Somes Sound by USCG mooring to hike a bit.
If you decide to sail from Bar Harbor back down the Maine coast I'd advise starting early because the afternoon sun is right in your eyes and it's a bitch to see the lobster trap buoys.
Oh, and one other thing. As you get toward Port Clyde and Penobscot Bay the lobster pot buoys are doubled up. There is one buoy that goes down the trap and another buoy about 15' away that attaches to the first buoy with a line that's about 6" below the surface. Don't go between those buoys (Unless you have a
full keel I guess).
Bill