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Thanks, I grew up in NYC and sailed LIS with my dad out of Branford CT for many, many years. We sailed from Branford to MDI, Halifax NS. and Bermuda, so I have been to Fisher's Island, Block Island, Shelter Island, Gardner's island, Cuttyhunk, Nantucket, Martha's Vinyard, Provincetown, Montauk even up the CT river etc. multiple times. I then spent 20 years exploring the coast of Maine in my own boats. My comparison is not based on ignorance of LIS.
Never implied ignorance of LIS, but chose to comment about the hyperbole regarding “an order of magnitude more interesting”. Comparing Maine to other areas is a lot like apples and oranges. Each area has its own characteristics that include positives as well as negatives.

I’ve made a couple of cruises to Maine and appreciate what Maine has to offer, but it isn’t an order of magnitude more interesting IMHO. One of my more memorable experiences was rescuing a fellow cruiser who got knocked down several miles off York and couldn’t reestablish the raw water prime for his engine. With no SeaTow or TowBoat US to help, I took him under tow unit he could work on the problem and motor under his own power through a serpentine, rockbound narrow channel into York Harbor. That experience was certainly was “interesting” and it was a reminder of how you need to be prepared for a more rural experience when you sail to Maine. Of course, that is also part of the charm—less crowded waters, at least in some places.
 

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Discussion Starter #42
There is little comparison between cruising Maine and Southern New England... so the apples and oranges comment applies.

As I live in NY - LI - CT area it is more a treat for me to sail down East... but it is also fabulous to cruise from the East end of LI out to Nantucket. Places like Newport are very special for all sorts of reasons related and not related to sailing. I think there is more variety in Southern New England. Unfortunately Southern New England is more crowded than ME and this is a down side to populous areas... more boats.

I love to sail both regions... but Maine is a special treat because for one thing it is not as accessible to me. Fortunately I can get up there in a few days. How cool is that!
 

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It most certainly is, for about 8 weeks per year. :wink
May June July August Septober. Nothing like brisk sail on Penobscot Bay in Septober! I've never hit anything, but always KNOW where you're "returning" to. Some pretty confusing nuns up home. Oh, and never tie off to a stationary dock and leave the boat for any length of time. I've seen my share of boats hanging by their docklines.
 

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?...Nothing like brisk sail on Penobscot Bay in Septober! .
Maybe, but it’s no order of magnitude more interesting than a typical Southern NE September sail. Kids all back in school, generally good breeze, all anchorages are available any time of day. All the joints are still open. It’s arguably the best sailing month of the year (assuming no canes brush the coast).
 

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Maine has something like 3,000 coastal islands, and a like amount of coastline in miles. Coastal mountains, tons of hidey holes. That's all. Somehow, I've always preferred being either out of sight of land or far enough so seeing anything doesn't matter. But I do like the coast from around Casco Bay to Winter Harbor best. I grew up there. Brings back memories. We were hang gliding on Megunticook Mountain many years ago while Bob Hope was playing golf at the local golf course. Used to punch holes in clouds down there. Then kids came along and that tends to divert your attention, reconsider immortality. Love to sail past Camden Harbor . . . where's those photos . . . I took a picture this past January and you could've skated on the ice across the Harbor (not advisable). The south side of the Lincolnville Ferry Dock (to Isleboro) was frozen solid as well. Even with a 14' tide. And I'm doin' the winter boatyard troll just for something to do.
 
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