Join Date: Feb 2009
Location: Old Greenwich, CT
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Some of my favorite kids' spots
I have to agree with some of the others that you don't need to go all the way to Boston to have a terrific cruise. Among the many fine choices pointed out by others (and maybe a couple of add-ons), I think some of the following locations would be kid friendly.
Branford, Essex (but you have to deal with a lot of traffic on the CT river), Mystic (aquarium and maritime museum). In fact you might make a reservation to stay at the maritime museum - would be a lot of fun for the kids. Port Jefferson, Dering Harbor and Cochles Harbor on Shelter Island, Sag Harbor (try to reserve a mooring, slips are expensive). Sag is a really neat town, you can see if the whaling museum is open. Eat at the back of Concha D'oro - good peasant italian food at reasonable price or you can buy food at the IGA and Barbeque at marine Park right off the water.
Three Mile Harbor has very good anchoring for swimming. A couple of restaurants along the shore, otherwise not much else there - though very scenic. They do fireworks for Bastille Day (July 14) if that works for you.
I am a big fan of Montauk. There are a number of choices of how to stay there. Check out guides and pick your poison. Duryea's is a little known treat for having shellfish (Lobster, steamers, clams, etc) on a deck with picnic tables facing a beautiful sunset. A little distance from where you will keep your boat, but worth arranging.
Stonington is another nice choice which would be a very short sail from Mystic (maybe trade a very short sail for a longer sail another day????). Take a walk to the point and go up on the lighthouse.
Newport is a great location, but where to dock the boat is the problem. Newport Yachting Center would be one choice. Avoid Christies like the plague, unless you want wall to wall bar crowd for your kids! You can rent bikes, go to the kite section of (I believe it is Brenton Reef park), take a tour of one of the mansions (the Breakers is the most common choice for first mansion tour). Lots of choices to eat, check guides for what you want. I was there pre-kids and loved Scales, but may not be in your budget and I'm not sure how kid-friendly.
Agree with SailingDog about Cuttyhunk. Great for kids. There is swimming in the channel that you enter in. Nice walks to the top of the hill for great sunset viewing. Really nice small fishing town -- very New Englandy!
Tourists or not, I think Oak Bluffs is very kid-friendly. Beaches available, rollerblades and bikes to rent, check out the candyland style houses (I forget the correct nomenclature). Any guide book will describe it for you. There is also a carousel there. Plenty of places to eat, and among the better equipped for things like showers, etc.
My top three of the above for kids would be Mystic, Newport and Oak Bluffs. Simple reason is lots of things to do with the kids. With 8 year old twins, I know how important that is.
Most of all, have a great time!