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Discussion Starter #1
I am a member of a sailing club in Massachusetts and as part of my membership I get a sailboat for one straight week in the summer. I will be taking the club's Pearson 36 out of Westport MA. Thinking of sailing to Newport and the Vineyard. I know luck plays a big part of it, but what week would you take from May to September?
 

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The water is very cold still in May. Avoid the week of July 4th. Last week of July and first week of August are the most crowded. We go the last 3 weeks of August. Sept is great. No crowds but have to watch for tropical storms.
Jim
 

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Hello,

IMHO the week AFTER labor day would be great. The water will still be warm, the wind should be decent, and the marina's will not be crowded.

If you want to swim or want more daylight, then going the week after July 4 would be good.

Barry
 

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Jim is right about the last week of July. That's when we (and a LOT of other clubs) hold their cruises. We're planning to get Nantucket this year, and all the spots you've mentioned are on our way there or back. Second or third week of July would avoid some of the crowd and have a chance at good weather, though the breeze may be lighter than in September.
 

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Discussion Starter #5
I was thinking the week after Labor Day would be ideal, I just don't think I can wait that long. Definately would like to avoid heavy crowds. What about the last week of June?
 

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Newport Jazz and Folk fest are always fun. At Fort Adams, you can hang out on the water and hear just fine. Good anchoring just to just north of the fort and lots of night happenings in town. Prime time. Jazz 8/1 thru 8/3 Newport Jazz Festival and Folk 7/24 thru 7/27 http://www.newportfolk.org/
 

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Hey Slayer,

I thought that you did this same trip in 2013. Did you not?

I am planning a week long trip, to the same destinations, that will co-incide with the Perseid Meteor Shower in August. The current plan is to sail from August 9 or 10, to August 16 or 17.

I did the trip at the same time last year with my sailing club, and we all had a great time. There was no problem with crowds. Many of us met at Third Beach in Newport, then all went to Cuttyhunk (there were few enough people there that I was able to anchor in the inner harbor!), then we planned to go to Lake Tashmoo (several boats did not make this stop), then everyone met at Edgartown. From there some went to Nantucket, some went to Chatham, and my boat went to Dutch Harbor. Boats came and left our fleet, so everyone had a slightly different experience.

One boat, a Gemini 30 Catamaran, was based out of Westport. I expect that he will be joining us again.

PM me if you would like detail.
 
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I was thinking the week after Labor Day would be ideal, I just don't think I can wait that long. Definately would like to avoid heavy crowds. What about the last week of June?
Last week of June may be crowded, as everyone will have their boats in the water by then, and al of the ports will be opening to accommodate them. I made a jaunt to Cuttyhunk during the second week of June, and none of the harbor businesses were open...
 

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Discussion Starter #9
Thanks for the info Eherlihy!! I did a short version in September of this year, just three days. Sailed over to Cuttyhunk, but nowhere else. I did fall in love with Westport and the area. Will PM you with more questions.
 

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You are getting good advice.

Late August through September is best. The water stays warm, and the crowds lessen, even as early as the second half of August…seems like a lot of schools start their sessions earlier and people leave. Even some of the local restaurants, etc., complain that it's hard for them to keep help through labor day due to various schools starting earlier, and families leaving.

Your hurricane risk increases with this strategy, but otherwise, that's what I'd do.
 

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The crowds in the Cape area are driven by the school summer vacation, when the schools get out the population in the Cape areas triples over night. So if you can pick and chose your time, I'd say go before the 4th week of June or after Labor Day.

As with other posters, I'd recommend the after Labor Day choice as the weather and water temperature are still summer, and places like Cuttyhunk, VH, or gasp! Nantucket, which would be elbow-to-elbow the week before, are pretty much empty.
 

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I was thinking the week after Labor Day would be ideal, I just don't think I can wait that long. Definately would like to avoid heavy crowds. What about the last week of June?

I will third or fourth the week after Labor Day. June is "iffy" lots of years with rain and sometimes a lot colder than you would think.
 

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The club cruises can fill up harbors, particularly if it's the New York Yacht Club. We've run into them a number of times at Nantucket, Edgartown, and Cuttyhunk. It seems these guys favor late July thru early August.
Later in August is probably safer. Water temps hit their peak as kids return to school and family boats are laid up for the winter. After labor day, amenities, like launch service at Block Island's Salt Pond, begin to dry up fast. By mid September, there is quite a scene in Newport during the boat show.
 

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Since no one has mentioned this, I'll chime in. Late Spring can be very foggy, especially around Chatham and Nantucket. Oftentimes it will not burn off until 11:00 AM.

Also be aware of the shoals at that end of the Cape, no matter when you decide to go.
 

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June is beautiful, but a bit of a crap shoot. Shore temps are great, but ocean water is still cool, so it will be chilly while sailing offshore. Whether places like CuttyHunk are open and in full swing will depend a bit on how stormy and warm the spring has been. Even then, only on weekends.

The week after Jul 4th will be the easiest to get moorings and slips or find an anchorage in the height of the summer. Once you get to Aug, you do start to risk hurricanes. We had to quick haul the weekend before Labor Day a couple of years back. Even if they don't threaten land, they can kick up some nasty coastal seas. Not every year.

The week after Labor Day is also great. Crowds die down dramatically but everything remains open.

Keep an eye peeled for regattas and/or festivals, where all bets are off. Newport is nuts year round. I've suggested to many to go to Connanicut, across East Passage, and take their ferry back and forth to Newport. However, some like being in the action. Countless places to go of all kinds from quiet to mobbed.
 
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I've sailed Buzzards and Mass Bay for around thirty years now. I might surprise you but think Oct. is the best month. Peak hurricane for the eastern seaboard is Sept. Winter gales don't set in until Nov. Everyone is gone. There is rarely launch services and most boats are on the hard. Water is still warm and winds even in Mass Bay or L.I. sound are usually good every day. Those areas are usually very light air July to Sept.. Stripers and blues have started their southern migration and fishing is excellent. You can cruise and have anchorages or mooring fields to your self. It's almost like exploring but still can go to all the interesting spots on land and restaurants without putting up with crowds. These past two seasons did fall cruises. Wife says she'll really miss those when we head south. The quiet and beauty of fall is so soothing.
 

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I envy you the decision. Just moved away from MA but had some of our best fun down among the islands. Your first choice is likely to be whether you swing East or West. Unlikely you can do Nantucket AND Newport (agree that Connanicut is a really good alternative to the latter) in a week unless you want to be sailing really hard core all the time.

The week after Labor Day is great but, depending on whether you prefer having the place to yourself or a bit more "atmosphere", you may not want to rule out either of the last two weeks of August. You may have to book a couple of moorings but you have plenty of advance notice as long as you are not too ambitious about how big a hop to make in any one day so that if the wind totally dies, you can motor.
 

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I've suggested to many to go to Connanicut, across East Passage, and take their ferry back and forth to Newport. However, some like being in the action. Countless places to go of all kinds from quiet to mobbed.
+1 for Conanicut. That's what my family has done for many years. We go in late July and early August and trailer our Catalina 22 and rent a house there. Its scenic. Of course everything is busy, but is usually good wind and the water is warm. We deal with the crowds - Jamestown is quiet enough and the ferry to Newport rocks..
 

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We sailed a Cal 33 "Cheap Sunglasses" out of Westport the week after Labor Day this year. The launch service at Tripp's had started closing at 3 pm on weekdays after Labor day, so call them to make sure you can get to the boat!

Otherwise I agree that it very pleasant to sail around New England after the Summer is over. The Newport Boat Show was also the second week of September. If you wanted to either engage with crowds you could go to Newport then, or miss them by going the week before or after.

We went to Manemsha and Cuttyhunk. The weather was OK for New England (some rain) and the water was warm enough for swimming.

We got a ride on the C.W. Hood 32 at the Boat Show (very nice!) but had to rush back to Westport because of the launch hours. The people at Tripps were very nice though. Just beware of possible reduced launch hours after Labor Day, so plan on a slip or using a dinghy more in the Fall perhaps.

There are far fewer crowds and generally as nice weather as anytime in the Summer in September (and October).
 

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The weekend after any holiday is usually the best time to go anywhere (sailing, skiing, etc) if you don't like crowds. The holiday weekends are the best if you do like crowds and to be part of all the action. It seems like most people here don't like crowds.

So it depends on what you want. If you don't like crowded anchorages, mooring fields and restaurants then the Sept and Oct advice is good. However, I also find that the week before labor day is usually pretty good as most of the kids are back at school or home getting ready for school and the week is fairly mellow in comparison to the rest of July and Aug. You get all the summer weather benefits and if you can extend your cruise to include Labor Day, you get an extra day.

If you are looking for some action, go 4th of July. If you can't go on the 4th and still want action, skip the week following the fourth and go anytime after up until the week before labor day.
 
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