Boston Sailing Center has great cruising guides for that area. If you want to look at other areas, try their regional overview

I used their guides when sailing from Chatham to Boston. They were really useful and informative.

One other note: call well ahead for mooring. Some places *cough*Vineyard Haven*cough* fill up quickly and may not respond with any sort of empathy or kindness if you tell them you're headed their way. Oak Bluffs was much friendlier.

 

One other note: call well ahead for mooring. Some places *cough*Vineyard Haven*cough* fill up quickly and may not respond with any sort of empathy or kindness if you tell them you're headed their way. Oak Bluffs was much friendlier.

A you are saying that Vinyard Haven takes reservations?

I heard the Block does not take reservations, is that true. If so when do you have to get there to get a slot. And what is the deal with the colors of the moorings?

 

Personally I liked Oak Bluffs on my Vineyard trips. Not a touristy commercial. Same with Edgartown

 

Dave,

Cuttyhunk does not take reservations. I have always managed to find a mooring ball, and have even been able to anchor in the inner harbor on occasion. Just get there before 4:00 pm if you want a mooring. If you go, plan to have breakfast at the Cuttyhunk Fishing Club - it is spectacular!

Block Island is a nice place, but I have never been there in August. I understand that many people get a mooring in Great Salt Pond, and keep the boat there while they take the ferry back and forth to the island. I've only been there in October, partly because I don't know if I can find a mooring in season. You really can't anchor in Great Salt Pond. For a short stay, I'd go to Newport or Dutch Harbor instead. There is plenty of anchoring space to the north of the mooring field of Dutch. . Dutch Harbor has a small shack that sells the best fish taco in Rhode Island. There is also a good restauraunt about half a mile up the road from the dinghy dock. Newport needs no further description. I have stayed at Point Judith's harbor of refuge, and it is nothing to write home about. However, I understand that Point Judith Pond is really nice.

On the west coast of Martha's Vineyard, you can probably find a spot to drop the hook in Lake Tashmoo. Even if you cannot, it is worth poking your nose in to have a look around. Vineyard Haven is too rolly for my taste, although I've never been into Lagoon Pond. I always grab a mooring if I stop there. I have always been able to find a mooring in Edgartown on the eastern side of the island. You can anchor out at Edgartown too, but it is very exposed to any wind out of the north.

Have fun!

 

There is anchoring in the Great salt pond in BI. On the North side. Just as you get in the channel through the jetties, turn to starboard..
Pretty far from the town and dingy docks, but you can find a few spots, but someone will no doubt anchor over your anchor...no biggie unless you want to leave early in the morning. it gets crowed in the anchorage, interesting when the wind turns..Nice to have someone stay with the boat and have a couple of fenders at hand.
If you have a shallow draft there is a second anchorage farther in, still on the north side...tons of Stinkpots there...
45 footer, you should have all chain, it can get iffy when the wind blows from the south. Many boat drag their anchors..
There are a couple of moorings that are right as you enter the pond, by the coast guard station, I can't remember the color, I think Yellow... these are usually left empty and can be used if you get in at night, they will move you in the morning.
You might be able to score a slip at Paynes, it is a "reverse in" type of slip with bare pilings for your bow, can be tricky when the wind blows, actually can be tricky anytime unless you are familiar with backing up in to a slip. Have your bowlines at the stern and lasso the pilings, walk to the bow as the boat backs in

Point Judith is also good for anchoring, the stay can get rough with the ferries' wakes, the north east corner is the best as far as avoiding the ferries' wakes. Those can clear the galley and table in a NY Second!

Cutty Hunk has Mooring balls outside the harbor, most always you can find some empty. They have a tube that stick out of the top, you need to thread your own bowline in there and cleat to the deck, I like redundancy, so I thread two lines in the eye, especially knowing that it gets rough with a north to east wind. Call the Harbor master if you want a slip, dock or mooring inside, might be full if you get there in the afternoon. Food stops serving on the dock pretty early, I think 5:30 or 6...
From there, early in the morning, like 7:00 AM, you can call the Menemsha harbormaster on the phone...(Stillmark Harbormaster I think is the correct town) and see if there is space on the moorings in the harbor. They have 2 mooring balls and raft up to 5 sailboats on those. Also have moorings outside of the harbor, same exposure as Cutty Hunk. Not good anchoring in either place.. Not much to do in Cutty, but Menemsha is the bomb. Active little harbor, very quaint, the buses run all over Martha's Vineyard. Check out Larsen's fishmarket for fresh catch all day.
A couple of restaurants and shops with in walking distance. you can take the dingy in the pond...my personal favorite place to go.
That's as far as I have explored...

This July we make sail for Nantucket Via Cutty, WoodsHole, and Edgartown ...Blue water sail back to Stonington or Pt Judith depending on the weather and wind.
Sounds like a fun trip. Enjoy!

 

The public moorings in New Harbor at Block Island are lime green and are first come/first served. Generally in July and August you have to grab one in the morning as it is vacated to get one. Forget about finding one empty if you arrive in the afternoon. The harbormaster does keep track of private moorings that will be empty and can be contacted to see if any are available.

 

David, You'll want to turn to port as you come into Great Salt Pond for the anchorage area, get there early, hard bottom, crowded, watch the PM wind. At Marthas Vineyard, Menemsha harbor is part of Chilmark, 2 mooring inside, a couple outside as well, watch the wind direction on the outside, lots of room to anchor. Cheapest deisel in the islands at the Texaco, and Larson's is not to be missed. I perfer Vineyard Haven, and Lagoon Pond is my favorite anchorage (3 days limit, then need to move), the drawbridge was being worked on last time I was there 6/1/16, hopefully complete now, only opens certain times of the day, mid-day and late afternoon as I recall. Tashmoo is very nice but watch your depth through the breakwater, best at high slack, think it's around 6'. Go up inside to 10 ' depths, dingy to shore at the south end, short walk to Vinyard Haven. Lots of anchorages in the Elizabeths depending on wind direction. Have fun.

 

At Cuttyhunk and Hadley Harbor there are places to anchor in about 8 to 10 feet low tide. DON'T! All weed bottom. You may think you are set but when the wind blows, you will be long gone. I woke up a couple just in time, they were dragging toward rocks at night after dropping in weeds and not setting HARD. Anchor in 15' low tide for good holding.

And watch the current at Woods Hole. You must turn 90 degrees heading eastbound...but the current doesn't turn and it will carry you into rocks. Fun times!

 

Thank you all.