Calling NY/Long Island (or Newport RI) experts!

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I'm going round in circles - anyone knowledgeable about trips from NYC? I want to add a few days onto our 5 night NY trip in August.
Plan is hire a car (Manhattan or JFK) then either:
A) 2 days on LI eg Greenport/Sag Harbour/Montauk, with possibly Riverhead as a cheaper base, (or earlier tip on here🙏Southampton). Then return car to JFK for 11pm flight home. (Did think of train, but fare for 5 people is $$ and then limited when we get there, unless we found one great base?) Or
B) 2 days on LI, ferry to CT, day and overnight in Newport, day in Newport or nearby, then v late flight home from Boston. Or
C) skip LI, go to Newport for 2 or 3 days and back to JFK or on to BOS.
But will the notorious LI traffic scupper these plans? I'm trying to make the drive out of NY not Fri or Sat, nor back on Sun eve.
We'd love things like: a little bit of beach time (with limited kit!), coastal stroll, shopping, cafe stops, seafood, drinks by the sea, maybe a kayak, vineyard visit, gilded age mansion, cliff walk in newport, a short whalespotting boat trip from Newport would be amazing!
If you've done something similar in peak season, was it doable, worth it? LI feels closer but maybe busier? Which version would be best overall experience?

Don't know about Long Island but Newport I would do for the day, then a few days in Boston with a whale watch, then fly out of Logan airport. The New Bedford museum is interesting and in a cute town with mansions and good seafood restaurants too.

Thank you. I think Newport does look interesting and I suppose it would make sense to look at Boston a bit more. There seems to be lots of cute towns all along the coast. I wonder if it would be less crowded and easier "to do" than Long Island?

I don't think it will be less crowded but it might be easier as in more tourist infrastructure instead of just summer homes.

Really it depends on if you want to experience more of a New England feel, I think it's a nice contrast to NY.

That seems like sooo much to try to pack into 2 days. If you just want beach, NYC has some great ones. Coney Island is great for the amusement park but Jacob Riis is just a lovely huge beach, great fun.

Honestly, you are trying to pack too much in for such a short amount of time. All of those areas that time of the year are $$$$, very crowded but admittedly very beautiful. Personally, I wouldn't bother with Montauk, but Sag Harbor is stunning. It will be very crowded, however.

Newport is also fantastically beautiful, and you have shopping, the mansion walk and nice beaches. But the streets are very narrow and parking is terrible.

If I were you, I'd have a few more days and spend them on Nantucket.. sigh...

I’d do Cape Cod and Boston over Long Island and New York any day.

I vote North Fork of LI (Southhold, Greenport, Oreint Point, Shelter Island)!

Drive out of JFK or take the Hampton Jitney.

Greeport has everything you want - beach, vineyards, coffee shops, ice cream, book shop, all walkable and major cuteness! Rent bikes and take ferry over to Shelter Island - cycle around. Or leave the bikes and take ferry to Sag Harbour.

Orient Point has wonderful beach, kayaks, those boards you stand on etc. It is low key, fun, easy going and not busy like Mass.

Jitney back to JFK or car.

I love it there too but it is MAD busy in the summer.

Newport has too many drunk students in the summer! At least that is what I remember.

Off season it is truly lovely.

@yesmen how long ago were you there...? This has not been my experience in the last few years! Too expensive now...

Greenport - last summer.

Rhode Island - last summer

Cape Cod and Boston - last summer

Thanks all, some v good info and advice here. I'd love more time for a decent road trip but we are stuck with limited days and as a family it may be the only time we'll do the USA together. Only my husband has been before. Our "kids" are between 16 and 21 -I know they will love NYC but we'd love to see another side of the country, albeit briefly. We don't NEED to do a long beach day as we'll do that on a short holiday in Spain. I do love a coastline on holiday, but I'm thinking we might not have enough time to do justice to the CT/RI coastline.

Do you think LI north fork would be less busy if we avoid going at the weekend? And my other question is would Riverhead be a decent, if dull, base for a couple of days?

I would advise against Riverhead. It is not great.

Greenport I has fun bars and a vibrant (but early closing - think 10.30/11pm.

yes - less busy during the week.

finding a place to stay may be your issue.

thanks again for all this advice.... currently having a rethink about it all. Too many lovely places to see and not enough time!