Ideas for a 4 week itinerary norwalk to boston

Lewie,
I doubt that you will 'always be able t find a mooring or slip in late July to August' as this is the peak season for cruising. It is also in hurricane season so you might luck out.
That said, I bet that you can find places to stop along the way but it really is peak season at Block I. Others will chime in here I am sure.
Do you belong to a yacht club that has reciprocity with other clubs (some are better then others at this)?
If you want to keep your sails of shorter duration I would suggest staying in the Sound and visiting places like Faulkner Island and maybe some of the harbors on LI to avoid the MV/Nantucket/Block I. crowds. Even crossing the Sound from where you are in the usually light SW winds of summer could take 3 hours or more.
If you are 'done' with the Sound then just hop up the coast of CT to RI and make your way to Boston. Just be sure that any leg of your trip could be longer then 3 hours due to 'misunderestimation' of some kind.
I hope that others can give more hands on advice as we have no kids.
Sounds like fun anyway. Enjoy.

The other point is a Hunter 26 may a bit on the small side and designed for more protected waters than the trip from LIS to Block Island, or from Block Island to Buzzards Bay. Is this the Hunter 26.5 or the 260.

While the boat would probably be fine for the trip in good weather, if the weather goes south, it'd be a bit dicey. We often have SCA type weather in Buzzards Bay, and while I go out in it in my boat, my boat would dwarf a Hunter 26 in many ways.

If you're going to go anyway... I'd highly recommend getting and reading The Coast of Summer-by Anthony Bailey about cruising New England in a Tartan 27, since it will be a good book to read and is about these waters. I'd also recommend getting The Cruising Guide to the New England Coast.

A few places that would be worth stopping:

Cuttyhunk Island, but get there early in the day to get a spot inside.

Menemsha, Martha's Vineyard, but you'll want to anchor in the pond, since the main harbor only has two or three moorings for private boats. Draft can be an issue for some people getting into the pond at anything but high tide. Don't try making the harbor if the wind is out of the north, it can be less than fun... in that case go to Tarpaulin Cove instead.

Tarpaulin Cove, on Nashuon Island, is a great stopping place and decent anchorage if the wind is out of the North-Northwest-West. The island is privately owned by the Forbes Family Trust, but they allow the beach to be used by boaters anchored there.

Hadley Harbor, on the eastern end of Nashuon Island, is a very protected anchorage that is nice to stay at. However, Woods Hole has fairly fierce currents, so check your Eldridge's. Also, the traffic through the Hole can make things interesting for a small sailboat. I'd only recommend this if you're going up into Buzzards Bay, rather than along Vineyard Sound, since you have to go through the worst part of the Hole to get there from Vineyard Sound, but not from Buzzards Bay.

Vineyard Haven, Martha's Vineyard, is a lot more commercialized in the tourist sense, and you do have to be wary of the ferries. Anchoring on the west side isn't bad and protected from anything but a North-Northeast wind. Lots to do there if you're into touristy stuff. I'm not.

Edgartown, Martha's Vineyard, is also a very commercialized tourist trap area. Not well protected if the wind is from the north, but you can always hide in Cape Poge Bay or Katama Bay.

Nantucket is almost impossible to get a mooring or slip in during that time period, unless you get there very early. However, if you have a shallow enough draft, you can always anchor in the Head of the Harbor, where the water gets pretty skinny. If the wind is from the south, you can also anchor outside the harbor, off the beaches. The eastern side north of the harbor's barrier beach is better IIRC, than the west, which is rockier and less good holding.

If you're planning on going north, through the Cape Cod Canal to Boston, I'd recommend the following additional places to stop:

Padanaram (Dartmouth). The harbor is very shallow, so be aware of that. Also, there's a swing bridge that you have to pass to get into the main harbor. Well protected from all but South-Southeast winds.

Fairhaven and New Bedford, which have a lot of maritime related sightseeing exhibits. The Whaling Museum in New Bedford is a particularly good one. If you do stop in NB/FH, let me know, and if I'm around I'll take you to a few good spots.

Sippican Harbor (Marion). Good spot to stop on the way to the canal, but not a whole lot to do there. Not protected from South-Southeast winds.

Phinneys Harbor is a good spot to stop before making the canal entrance, as it is right there at the mouth of the canal. Again, not much to do there... but well protected from most directions except West winds, unless you hide behind Toby's Island. The other alternative is Onset Harbor, but Phinneys is easier to get into IMHO and larger.

Cape Cod Canal passage should not be attempted if the wind is from the southwest... If the wind is north or east, you'll have a much easier time of it...but with the wind from the southwest, there will be standing 6-9' waves there...and it won't be much fun or very safe. Check your Eldridge's for the currents, since the current is quite swift through the canal. Just before the Cape Cod Bay side exit, there is a small harbor (Harbor of Refuge) on the southern side. This is often a good spot to wait if the wind is out of the Northeast, since the same problem can happen on this side, but less so. They will not allow you to sail the canal, it must be done under power. IF your engine is not reliable-DO NOT ATTEMPT IT.

Provincetown or Wellfleet are the only two harbors I'd try to stay at on the inside of the Cape. Both are fairly well protected, but Provincetown has a lot more to do than Wellfleet does. Be aware that it's a pretty long sail for a smaller boat to go from the canal to either.

On the mainland side, you've got more options, these are two I'd recommend on your way up to Boston.

Plymouth Harbor or Duxbury Bay are good choices if you're planning on going up to Boston. Plymouth of course has Plimouth Plantation, and the original Plimouth Rock... the rock would probably fit under my dining room table, so don't be surprised at its size.

Cohasset Harbor is a good stopping point before entering Boston Harbor proper, if the wind is out of the south. It bites if the wind is out of the north.

The Boston Harbor Islands are a state park and have specific requirements. From their website:

Moorings: Limited docking space is available for private boats at Georges Island on a first-come, first-served basis. On all other islands, docks are available for off-loading only. Small prams are available for anchoring off-shore. For information on moorings for private boats at Bumpkin, Georges, Peddocks and other Boston Harbor Islands, Call 617-223-8666. For reservations and technical information, call 617-241-9640.

Click to expand...

Boston, itself, you'd want to make a reservation for a slip at a marina more likely than not.

I hope this helps.

Lewie,
Here's a few short hops through my area -
Watch Hill - has a very large and wave protected (but not so much wind protection) anchorage. The town has a famous old Carousel and a few ice cream shops for the kids.
Point Judith - There is the 'Harbor of Refuge' but that can be very uncomfortable with wind and more waves than you would expect. We ususally (with a 5' draft) go way up into the Pt. Judith Pond. You MUST stay in the marked channel up to Plato Island, take a right turn (edit) after Plato or after Gardiner, and there is an anchorage to the east of the area between Plato and Gardiner Islands. Nothing to do and no place to go but a nice fairly quiet place.
Third Beach - After you pass by Newport and NGBay you can enter the Sakonnet River and there is fairly large anchorage that is somewhat protected and you could dingy in to the beach for the kids.

Your 26 will be fine for the trip as most of it is in sheltered waters. Your hop to block and to buzzards through the canal will be your challenge but very doable.

I appreciate the need for short hops do to the kids. Forget Faulkner island in Guilford. It a restricted and no landing allowed. Consider stops on the CT river like Essex You then from there you can shoot across the sound to Greenport. (has a carousel for the kids) You can pick up a mooring at Jacks on shelter Island and take the ferry over to greenport. Spend the day swimming at Orient point harbor too. Leave greenport and swing over to sag harbor (bring your wallet). Plenty of anchoring and fairly well protected. Other choice would be three mile harbor. From there you can hit BI and from BI to Buzzards and on to the canal. Save Narragansett for the and Mystic for the trip back

I'll be heading up to Boston myself in July. My son lives there.

You might want to re-think this voyage, or at least, the itinerary. If you sail only 2~3 hours per day after day one you will be just east of Bridgeport, perhaps Stratford. At the end of day 2 you will be between Madison and Clinton. Day three gets you to Niantic Bay, short of New London. This means you will make Mystic toward the end of your first week.

I too heartily recommend Bailey's book "The Coast of Summer". It will make you want to get under way and let the wind take you where it will. But he and his wife wandered about in three month increments. Every spot the others have mentioned are worth the voyage. But as Marshall Dodge said "You can't get there from here". At least not in the time frame you have laid out AND limited transit times.

Perhaps planning longer days or less optimistic distances may be in order.

From my sailing on the LI sound you would really have to be moving to go from Northport harbor to Oyster Bay in 2 to 3 hours unless the current was perfect and that has to be the shortest trip you could make

Being compleatly serious most of the harbors on the LI side take 1 hour to leave or enter which will use up 2 hours a day before you even start sailing

Trust me on this as MY wife is a 3 hour sailor which pretty much means the boat does NOT leave the Northport area with her onboard


Northport to (Port Jefferson / Rocky Point / Mount Sinai Area) is 16 miles once your outside the harbor which would be again real hard to make happen in under 3 hours


And your really going to have to watch the WEATHER trends as 2008 set and all time thunder storm record it was a summer of once in a lifetime events about once a week

I am going to try to work up the Sound in short increments on the CT side

Norwalk to Southport, or Black Rock.
Milford CT
Branford or Thimble islands
Guilford
Clinton
Saybrook
Niantic
New London
Noank, Mystic, Stonington, Fishers Island, or Watch Hill
After that, there is a long stretch to either Block Island or Pt Judith.

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!