As title indicates, taking son out to LI, New York before college drop off. Plan is Montauk but open to feedback for eateries, landmarks and other noteworthy stop offs. Would love any suggestions.
I assume he’s going to SUNY Stony Brook?
Montauk is just gorgeous, though I haven’t been there in a million years. It tends to attract a lot of families; light years from the busier Hamptons.
But either way, the south shore beaches are amazingly gorgeous.
Block Island is a great destination. Take the ferry from Montauk.
Montauk is beautiful but overrun with partiers in their 20’s on weekends (a real problem for this formerly kind of sleepy small town and its police force). Aim for a weekday visit.
@bjkmom
No he’s at Yale. Just a fun detour and visiting my grandparents neighborhood in Queens. 
@jrpar we are aiming for a Monday.
It’s been a long time since I’ve been to Montauk but we always enjoyed eating at Gosman’s Dock. Montauk is not sleepy and quiet like it used to be… we used to stay at a simple motel, the Royal Atlantic… not sure if still there. There is Gurney’s Inn and Spa which has become very upscale.
The shortest trip would be to Port Jefferson, then take the ferry to Bridgeport to get to New Haven. Montauk has changed dramatically and many would say for the worse in the last few years, as noted above, overcrowded and lots of young partiers. If you do go out to Montauk you could return via ferry at Sag Harbor Shelter Island then another ferry to Greenport then go east to Orient Point, take a ferry to New London and drive west to New Haven or go west from Greenport to the Port Jeff ferry. I don’t remember a ferry from Montauk to Block Island (there is one from New London, CT to Block Island). Montauk is a long drive from Queens.
@lefthandofdog thanks!
I’m contemplating the ferry from port Jeff to Bridgeport but not committed yet.
I remember taking the drive from East Rockaway to Montauk when, as a kiddo, we would visit east coast relatives. I thought the drive was ENDLESS but mom would reward us with Carvel ice cream (we didn’t have it in Ca) It all seemed well worth the trip back then. Hope it isn’t too millennial 
The North Fork is very nice and not as crowded as Montauk or the Hamptons. Southold, Greenport, etc. and you can take the ferry from Orient Point that I think goes to New London.
My son-in-law grew up in the North Fork area and he always brings pies us from Briermere Farms, which is in Riverhead. These are amazing pies. In season you can also buy farm produce. If you like pie, try this.
Absolutely recommend the ferry so you aren’t sitting in city bridge traffic on a weekday.
What do you like? Here are some options based on different interests:
Whale watching, historic lighthouse, trinkets, beach walk: Montauk. (Use one of the ferries)
Vineyards/ wineries: north fork (use Orient Point ferry).
South shore ocean beaches: Fire Island beaches (e.g., Ocean Beach) , Robert Moses, Smith Point, Jones Beach or Long Beach (the latter two have nice long boardwalks to walk). Ocean Beach is the most remote- requires an approach by walk-on ferry, no cars on island, people shop in the town with red wagons; Long Beach is the most urban, with apartment buildings. Ocean Beach and Long Beach have a choice of restaurants in their very different feeling towns (small remote village vs. small city), whereas Jones Beach, Smith Point and Robet Moses are pretty much just fun in the sun. (Drive in from city if going to Jones Beach or Long Beach.).
North shore charms: Port Jefferson is a cute tourist town right off the car ferry, adjacent to Setauket with its West Meadow Beach (beautiful, with rocks/shells in sand- great for beachcombing, and calm Long Island Sound waters) and Stony Brook with its historic mechanical eagle at the post office that flaps its wings on the hour, is historic grist mill, the Long Island Museum of American Art, History and Carriages (historic carriages, art of Williams Sidney Mount, etc.), etc. Charming restaurants in Stony Brook include the Three Village Inn (near the post office) and The Country House Restaurant (near the museums). (Use Port Jefferson-Bridgeport Ferry.)
Historic Gold Coast Houses: There are tons on the north shore. One good option is the Vanderbilt Museum and Planetarium in Centerport, which is good if you like to combine a tour of a historic mansion with a planetarium show and displays of wildlife (from mollusk shells to fish to taxidermied birds and animals), all in different buildings on the pretty grounds with a view of the Long Island Sound. Nearby town of Northport has a waterfront park and dock on the harbor, and a lot of charming restaurants on its main street. (Use Port Jefferson-Bridgeport Ferry).
The south shore beaches, whether by going to Montauk or the other ones I named, may be one of Long Island’s most distinctive features. If you are going to visit relatives in Queens, you might try approaching from the city and check out Long Beach or another ocean beach on the west end of the island (I am sure your relatives can recommend a favorite), or visit the New York Aquarium in Brooklyn.
Enjoy!
@TheGreyKing wow! Thank you! Much appreciated. Will run by DS and see what sticks. It all sounds wonderful
We just arrived home from a week’s vacation in Montauk with our two kids, one of whom is leaving for college next week. They both loved it and asked to go back next year (this was our second vacation there). We are from Long Island and have family on Shelter Island, so have spent a lot of time on the north fork and Shelter Island Given the choice, I would pick Montauk hands-down over anywhere else on the island, especially with kids. There is so much to do out there, and the beaches are beautiful. I was amazed at how crystal clear the ocean water was. Montauk has a reputation for partying, but in two trips there, we didn’t notice any bad behavior. The biking there is fantastic, as the hiking and fishing. You can rent little sailboats on Fort Pond, and take surf lessons at Ditch Plains. You can also do a day trip to Block Island from there. There are some really nice restaurants too - we had some great meals at Harvest, Navy Beach, Flagship and the Lobster Roll. The only negative to our trip was the price - Montauk is very expensive.
ps If you are out on the North Fork, I second the recommendation for Briermere Farms - I picked up two pies on my way out to Montauk via Shelter Island, and they were gone in a minute. Their raisin bread and peanut butter cookies are hit as well. Claudio’s Clam Bar in Greenport is a fun spot for lunch.
Most of the time the ferry actually doesn’t save time over driving. We took it yesterday thinking the Friday traffic would be a nightmare… but bc you have to get to the ferry at least 30 minutes early (with a car) and then it takes time to get off, most of the time it’s either a wash or even slightly better to drive. Yesterday, in fact, driving would have been slightly faster. BUT… the trip feels much shorter on the ferry, and it’s more pleasant, and sometimes driving through metro NY is a nightmare. With the ferry, you can predict your maximum travel time much more easily.
The ferry isn’t faster, and it’s definitely a lot more money, but it is far more relaxing and fun.
Please look up their schedules online and reserve a spot lest you find yourself waiting for hours and not getting on. Monday will be easier but it’s no guarantee.
BTW, just outside of New Haven are the Thimble Islands. You can take a short boat tour around them. Most of them are tiny and have houses on them. The largest one belongs to Yale so, who knows, he may end up doing research there.