We are going to Montauk this summer. Where else should we go?

Greenport looks interesting. I am going to explore that a little further. I am curious, Why Mitchel park or Townsend Manor Inn over Greenport yacht yard or Stirling Harbor Marinas? Is it because they are the same side of the bay as town, better facilities?

If you have a dinghy, it’s a 5 minute ride across the Harbor basin from Stirling Harbor Marina to a public floating dock in Greenport. The dock is directly across from the small sandy peninsula at the entrance to Stirling Basin. Town is a then short walk down the street from there.

Although Mitchell Park is quite nice & at the center of town there is no pool. Townsend, Yacht Yard and Stirling Harbor all have swimming pools and are quite close to that small sandy beach. This might be a big plus with kids!

Our home port is Stirling Harbor. The facility is very well kept, clean and in addition to the pool and van shuttle to town it has a terrific Italian restaurant, Portobello’s (one of our favorites). There is also a big new clubhouse and a valvtech fuel dock at stirling but fuel can be $$$. There is a vineyard contacosta ( might be spelled incorrectly) which has a beautiful view of the LI Sound that’s a 10 minute walk from Stirling Harbor too.

PM me if You need any help or local advice. Greenport is a great spot to go.
 
We have been going every year to Greenport for the last 3 to 4 years.... We love it... I would def say at Mitchell park, Thats where we always stay... Then we usually go to shelter island to a restaurant called Salt... Its on the back side of the island... If they don't have any spots for dock and dine then we head over to sag... You can get a morning for a day and the guy on the tender will pick u up and drop u off... A lot cheaper then getting a slip... Its like 6 bucks a person or 20bucks unlimited... And the morning is free... Its a great deal.... And the guy is super nice with a really nice tender...
 
We shoot across to Greenport from CT a couple times each year. I've stayed at Sterling, Townsend and Mitchell's.
Now, this is just my personal opinion...

Sterling was really clean, great pool, restaurant, and amazing bathrooms. Staff friendly and accommodating. Taking the shuttle into town was a little annoying having to depend on their driver's availability.

Townsend has a more family feel, the pool is large with plenty of room to spread out. Cool little bar/snack shack too. The restaurant was like going back in time. Laundry and bathrooms are in need of updating. Price was right. Walk into town wasn't too bad.

Mitchell's Park is definitely right in the middle of the action. Great view of the green and Claudio's right from your boat. No pool here which was ok for me, however, I felt that the bathrooms had a "prison" type feel with all the stainless and concrete.
(when brother and sister come along I point them to the marina facilities)
 
We are heading down to Montauk this summer for our week long trip. We have our 11 and 8 year old girls with us. Looking for other places/marinas we should see in that area when we are down that way from MA. We were thinking Mystic for a few days and then head out to Montauk for 4 days and then hit Block On the way back but we are open to seeing new places.

One of my favorite places is Cuttyhunk Island at the end of the Elizabeth Island chain. If you haven't already been there it is a stunning anchorage and a very cool island to explore.
 
One of my favorite places is Cuttyhunk Island at the end of the Elizabeth Island chain. If you haven't already been there it is a stunning anchorage and a very cool island to explore.
We like Cutty too. It is like going back in time. We won’t make it on this trip but we will be there a couple times this season.
 
Jeremy

I think you've got all the ports identified by others on this thread. When my kids were the age of yours they could tolerate about 4 hours underway before they got antsy. If you don't need to stop at BI to break the trip up I would definitely do MYC for 4 nights, you can really get the feel and relaxation of the resort over that duration. Your best choices after that are Greenport or Shelter Island. They are very different ports. In Greenport you can stay at the town marina (Mitchell Park) which is right in the middle of everything or you can stay at Townsend Manor marina, which has a pool, bar and restaurant and bbq area and is about a 10 minute walk to downtown. On Shelter Island there's two marinas, Island Boatyard and Marina and Coecles Harbor Marina. Although both have a pool, Island Boatyard is more suited to kids. Shelter Island is a VERY quiet destination. Great restaurants, interesting scenery but it's no more than a 2 night port, unless you're just looking to unwind. I wouldn't bother with Sag Harbor or East Hampton, not much for kids there. On the south shore of Long Island, further west of Montauk is the Westhampton Bath and Tennis Club, but it requires you to enter either Shinnecock or Moriches inlets and transit the ICW. Further west is the Federal park Watch Hill. Great transient marina, with an Ocean beach, but they do have a mosquito issue. Further west of that are a number of great marinas on Fire Island with honky tonk little towns and great Ocean beaches. Accessing any of those through Moriches is about a 2 1/2-3 hour trip from MYC and 4-4 1/2 hours if entering through Fire Island inlet. To remove any speculation by checking my bill from last season, MYC is $9/ft. + $45/night electric (single 50/250) + $15/night resort fee. Feel free to pm me if you have any detailed questions on any of those alternatives.

Wow, let me get this straight. If I were to bring my 400 Sundancer from little old Lake St. Clair through the St. Lawrence Seaway out to the Atlantic and visit Montauk YC, I would pay 40 x $9 + $45 + $15 = $420 per night???? I did youtube the place and it looks nice, but I guess I'm not seeing the $420 per night worth. I wonder what it would cost to keep my boat there as my permanent dock for the summer?
 
Wow, let me get this straight. If I were to bring my 400 Sundancer from little old Lake St. Clair through the St. Lawrence Seaway out to the Atlantic and visit Montauk YC, I would pay 40 x $9 + $45 + $15 = $420 per night???? I did youtube the place and it looks nice, but I guess I'm not seeing the $420 per night worth. I wonder what it would cost to keep my boat there as my permanent dock for the summer?

Well....no, for 2019 MYC has increased the resort fee to $20/night so you’d be $425/night. Seasonal dockage is $300/ft. plus metered electric. They estimate for my boat electric would be approximately $1500 for the season. Better hurry, they only have a few slips left.
 
Probably a bit more. They charge by actual LOA, and they want a 3 night minimum this summer.
I’ve got a wedding to attend out there in July and considered taking the boat out there and staying on it rather than having to rent a dump for almost a grand a night. Most of the VRBO’s and Air BNB’s want a week minimum stay.
Honestly, spent lots of weekends in Montauk years ago before it got trendy.
Nice place, but not worth what they want these days.
 
We just got back from out first trip down to the LI area. We had a really great time. Thank you all for the info you provided as it was helpful in Planning the trip.
Per recommendations we wanted to stay at Mitchell park but they couldn’t accommodate us (I sent in the request back in the winter sometime) so we went on the waiting list there. Our second choice was Stirling and then the Yacht yard. Both of those didn’t have an availability so we went on the waitlist there as well. Just before the 4th we got a call from Stirling that they had a slip so we took it. We set out for Greenport on Saturday morning July 6th in dense fog leaving Falmouth MA. Thankfully for HD radar and AIS it made the 3.5hrs of sense fog bearable. The dog didn’t lift till we got to Gardiner’s Bay just last Montauk. It was nice to see some of the scenery on our way in.
The folks at Stirling were great and the facility was great as well. The kids enjoyed the pool and we used the dingy to go to town during the day and Uber at night. We had a great meal at Lucharitos’s and watched the scenery at Claudio’s on Sunday.
Monday we left for Gurney’s Montauk. Montauk was much quieter than I expected. It picked up on Thursday as the marina started to get busy again.
Monday afternoon we checked out the lighthouse and walked around town. We spent a day at Gurney’s beach resort which was really nice. Another morning we did a horse back ride on the beach.
We had a great Meal at Harvest and Scarpetos At Gurneys. I took the kids tubing in Lake Montauk and other than that we utilized the pools and took dingy rides around looking at all the hardware there.
On Friday we left and heading for Block for the weekend. We planned on grabbing a mooring or anchoring there but when we got there I hailed Champlins and asked if they had a spot for us where we wouldn’t get rafted and they did so we took it. We hit town that night and got dinner there was well. Saturday the kids hit the pool and we took the dingy to the beach. We went to the oar for dinner and then back to Champlins for cocktails.
Over all a great trip with perfect weather. Thanks again for the help with stops, we are looking forward to another trip down to LI in the future.
 
We were at Champlins too this weekend. We saw your boat, it’s a beauty. In fact, I gave you a wave when you were getting ready to leave. I was in the 8’ dinghy with my wife, three kids and all our beach gear heading out of the horseshoe. What a weekend it was!
 

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