Some insider tips:
Seal Bay - Vinalhaven - One of the most beautiful spots on the coast.
Long Cove Vinal Haven - Beautiful spot if you go up in.
The Basin Vinalhaven - DO NOT take your boat in there. I've been in multiple times, mostly by dinghy, but now that I am older I won't do that again in the big boat. I suggest anchoring in Long Cove, next door, and taking the dink over for a lobster bake on one of the many small islands that dot the Basin. One of the most beautiful spots on the coast.
YouTube - The Basin - Vinalhaven Island, ME
Winter Harbor Vinalhaven - Simply amazing you can go way in past the big rock and no one else will follow you
Carvers Cove (Not Carvers Harbor) Best sunrises on the coast and no one stops here...

Sand Beach - Marshall Island (great day stop) Marshal Island is a must do. Excellent hiking trails and an amazing beach. In settled weather you can stay overnight.
Frenchboro / Long Island - This island has best lobster on the planet due to the cold waters around it.. This is is second best hike on the coast and you shaould plan to spend a day hiking the perimeter of the island. Bring a back pack and pack lunch. Also bring a camera and you may wear out the shutter button.. I have ALWAYS had excellent holding just outside the moorings beyond the ferry dock but Lunt's always has moorings if you get there early enough in the day. This and isle Au Haut fill up fast so get there by 10:00 or 11:00am....
Wreck Island - Merchant Row - You will likely be the only boat.
McGlathery Island (West Side) - Great beach for a lobster bake and a really cool island to hike. You can anchor on either the East Side or the West. Easy side has some granite ledge that extends out so be sure to back down to assure your anchor is not skating on solid Maine pink granite...
Hells Half Acre (North Side) - Great spot -

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Isle Au Haut Thorofare - Moorings only, put money in coke bottle, best hiking ANYWHERE on the coast. A few of the moorings are tight but I have seen 60+ footers in there. Plan to spend at least a full day hiking the trails of Acadia. Duck Harbor is a nice spot too but has lots of granite and can be poor holding. I have seen more than one boat on the rocks there. If you want to go to Duck Harbor take the dingy from the Thorofare and gunk hole it...
Duck Harbor view from Duck Harbor Mtn.
Burnt Coat Harbor Swans Island - Go in and pass the rental moorings near the big building. Go past all the fishing boats and anchor up in the cove roughly across from the church. No morning lobster boat traffic and a nice peaceful spot.
Over Rated Spots IMHO (as a local YMMV):
Camden
Pulpit Harbor
Perry Creek (is still beautiful but gets crowded and is now chock full of moorings)
SW Harbor
Rockport
Tennants Harbor - Cod End is now closed :cussing: so this makes Tennants even less of a draw.
Rockland - Rockland has everything you'll need so is great for that but not for the "real Maine" feel...
MDI / Bar Harbor - Stay at Northeast Harbor instead and take the free Island Explorer bus system to anywhere you want to go on MDI including Bar Harbor. The Island Explorer bus system is tremendous & free. If you go to NE Harbor there is a laundray service that will pick up your laundry, wash, dry, fold and return it. A great hike from NE Harbor is up through Thuya Gardens then onto Jordan Pond for their unbelievable popovers. You can also take the bus to Bar Harbor and then on the way back have it drop you at Jordan Pond and you can then hike back to NE Harbor. This hike takes a few hours.. So much to do and see on MDI and NE Harbor is a great spot to do this from..
Under Rated Spots IMHO:
Castine
Belfast - Great eclectic fun little Maine town.
Northeast Harbor -
JO Browns North Haven - Fox Isle Thorofare
Stonington - Anchor off town and can provision at the store which is right off the town docks where you can tie your dinghy
Provisions, within walking distance, are sparse along the Maine Coast these days. Rockland, Camden, Belfast, Castine, Isle Au Haut, NE Harbor and Stonington are about your best bets in Pen Bay..
PS Never, ever pass up wind or up current of a pot buoy!!!
