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Eastern Long Island

4K views 22 replies 12 participants last post by  RobGallagher 
#1 ·
Thinking of exploring around Shelter Island, Sag Harbor, Greenport, etc. I've spent a lot of time, many years ago, in Montauk and have been to Sag, but have never gone ashore on Shelter or others.

Any tips or recommendations appreciated. We like everything from secluded quiet to a nice restaurant and some activity.
 
#2 ·
The Shelter Island area is great. We've circled it a couple of times, stopping off a different spots for the night. Greenport is a nice town with good restaurants and a classic marine store (Preston's) that is fun to explore. The new town marina is a good place to spend the night. You can also get a mooring in Deering Harbor across the way and take the ferry to Greenport. Coecle's Harbor on the east side of the Island is a popular spot to drop the hook (with good reason). A narrow channel in so watch the charts carefully. Haven't been to Sag Harbor in quite a number of years, so can't comment on the current situation there.
 
#3 ·
Its tough to get a big boat in most of the nice places without mucho planing

FWIW when we also has the 20' powerboat it was tough to even drop into Sag Harbor for lunch without spending more docking than a high end lunch cost :)

Up at Port of Egypt there are some slips while you dine but again your boat is to big

I like to anchor out in the federal area by Rams Head on the east side of the Island

The southside by the south ferry is my favorite just have to be careful with the draft and i used go all the way up into West Neck Bay BUT that was and draft event even with the J24
 
#4 ·
Hey,

There is a very good cruising guide for Peconic bay here:
The Boater's Cruising Guide for Eastern Long Island, NY

I have personally been to Orient, Greenport, Shelter Island, and a few others. Do Not go to Orient By The Sea. The people are very nice but the place is tiny and I could barely turn my 35' around. In Greeport I like the Townsend Manor Inn. The marina is small but walking distance to town. The harbor (stirling basin) is quiet, unlike the town marina (which is nice, but exposed and affected by the ferry).

Good luck,
Barry

Good luck,
Barry
 
#5 ·
We did Shelter Island a few years ago. 6 foot draft, no issues. But then we stayed at the more remote places, not the harbor up by Greenport.

We picked up a mooring in Sag Harbor for $150 for the night, on that same trip. Watch the chart carefully at Sag and getting into Coecles harbor (really more of a beautiful lake than a harbor). Coecles had a dredged channel that's narrow, but no issues. (I think there's also a rock east of the approach to the channel that locals marked with floating plastic bottles -- at least that's what I guessed it was as I stayed away from it.)

Regards,
Brad
 
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#6 ·
Thanks for the feedback. Keep it coming, if any other advice.

Just for clarification, we favor being at a mooring rather than a slip. Anchoring is standard for us too, as long as holding is sound and it isn't too crowded. I always want to have an anchorage in my hip pocket, as I dislike making reservations and having deadlines.
 
#10 ·
We are based in Three Mile Harbor, also an excellent stop with some good restaurants. East Hampton Point has a dinghy dock. There is a new restaurant at the former Boat House at Harbor Marina. Coecles is beautiful. The only restaurant that is convenient is Rams Head Inn, but that was very nice a couple of years ago, and I believe it has a beach for dinghies. Sag Harbor is expensive, but has a wonderful town right near the main pier, and a great assortment of interesting boats and super yachts.
 
#11 ·
A suggestion from James Kidd, another local sailor:

"This past weekend I came across a secret (I guess, not anymore) gem…

In West Neck Harbor, located on the Southern tip of Shelter Island (just west of the south ferry) there is a small marina that has restored an old wooden sailboat and converted it into an outside bar, complete with raw bar (great oysters) and appetizers.

The best bet is to anchor in the shallow harbor and take your dinghy in for a cold one, and a dozen oysters…."
 
#13 ·
Probably thinking this is unusual coming from a Cheasapeake guy, but we travel to the LI Sound every year as well as points north up to Marthas Vineyard.

Making a circumnavigation of Shelter Island or visiting some of the beautiful anchorages/ towns there was one of our suprise discoveries a few years ago, and no trip now is without a visit to at least two places there

As mentioned Deering harbor is a great anchorage for Greenport a neat little town with good basic seafood restaurants. Also the town marinia is redone and a good stop for a slip

We have found anchorages in Hogneck Bay as well as Cuthogoue Harbor ( Little Peconic Bay) beautifuyl as well as serene, biut can be hot on stifing summer days

West Neck Haebor near Dickerson Creek is a noice wooded anchorage with good protection and then their is Sag Harbor. A very expensive place to say, but worth spending a few days. tremendous restaurants.. One of the best provisioning stores ( Schivones) . We have takinen a slip (4 a foot) and anchored outside the harbor ( tons of traffic) I would recommend anchoring in Smith Cove ( about a 20 minute dinghy ride ride for a great experience.

PM me if you want the names of some of the restyarants should you choose one or all of these places.

dave

Dave
 
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#14 ·
We anchor most of the time. Three mile has lots of room. Cockels is too crowded most of the time w/ too many generators. West neck is nice but small anchorage. Nice quiet spot up from Orient just past the light on the way to Greenport. Smith cove can be nice but sometimes crowded.
Beware going ashore on Shelter. The dear ticks are numerous.
Jim
 
#19 ·
Hey,

I stayed there for a night in the summer of 2010. The place is nice, but very small and required some very tight turns to get into and out of. It was difficult to maneuver my 35' O'day. If your boat is smaller and / or very maneuverable it might be OK. Personally, I would not go back. Nothing against the people, they were nice. It was just too difficult to try to turn around, etc.

Barry
 
#17 ·
Cruise recap

Thanks to all for the help. We got home last night after two weeks out. Here's what we did.

Day 1 - provisioning in RI, helping friend ready his boat to join us around week 2.

Day 2 - RI to Dering Harbor on Shelter Island. Longest cruise up front to get things going. Head current for much of it, so it took nearly 10 hours of beating into the wind/current. Moorings were $95 per night!! It was worth a visit, but I doubt we'll go back. People were nice and friendly. Well protected cove, except for northerlies.

Day 3 - Stayed on mooring in Dering, but took the dinghy over to Greenport and toured around Sterling Harbor. Greenport is a nice little town worth visiting. The famous Prestons chandlery is a bit over rated, but still worth browsing. I can occupy myself in just about any chandlery or hardware store.

Day 4 - Shelter Island to Three Mile Harbor. Circumnavigated Shelter Island in 20 kt winds with gusts near 30. Current runs pretty strong on the south side near the ferry. We skipped Sag, as the winds were staying up all night and wanted more protection in the harbor and we've been to Sag before.

The harbor is huge, but you need to cruise to the western side to get any protection from prevailing wind.

Day 5 - stayed in the harbor for a night, just to relax. We walked to East Hampton for exercise (3 miles away, that's where the harbor got its name). We were not impressed. Its just showy, with little to be showy about.

Day 6 - Three Mile Harbor to Fisher's Island West Harbor. Expected light winds, but got 15 kts on the beam and rocketed to FI in two and a half hours. Anchored in West Harbor, which has plenty of room and great holding. Took dinghy to Yacht Club, which has a bad reputation for guests, but couldn't have been nicer to us. We asked if they had a transient slip available for the following two nights and they did. Fixed dock, but water and power were welcome at $3 per foot.

Day 7 and 8 - Stayed in slip at Fishers Island. Family took the ferry to meet us there, as we used to vacation on the island as kids. Ran around to see the old sights, BBQ, lobster, all the old traditions. Picked up my daughter and her friend to come with us for week two.

Day 9 - Fisher's Island to Cuttyhunk. Cutty is a very familiar place for us. Great stop over or day trip. We used it to rendezvous with a friend to flotilla for the next week.

Day 10 - Cuttyhunk to Edgartown (Martha's Vineyard). Great weather, but made a big mistake. Slept in at Cutty, went back in to town with kids, then decided to look up the current through Vineyard Sound. Right on the nose all afternoon and it can be a brutal 3 knots. No wind and we had to motor the whole way. It took over 5 hours. Again, met more friends on the Island and had dinner. Edgartown is a great harbor and the town has plenty to do. Wish we had stayed longer.

Day 11 - Edgartown to Nantucket - Another long day with little wind. Planned to get out in time for favorable current, but getting everyone going was slow and we hit it again. Not as bad as prior day and we have a three day mooring reservation, so we know we'll just kick back once we get there.

Day 12 and 13. Very relaxing time, saw July 4th fireworks from boat in mooring field. We thought they might be too far away, but they were great. The best place to watch is about a mile from the dinghy dock. The thought of walking back at 10 pm with all the crowds was unappealing.

I have to say that Nantucket offers a lot, if you can get there. Moorings were $75 per night, but seemed to be in very good condition, with adjustable anti-chafing. A skiff meets you in the channel and escorts you to your mooring. Then another comes along with literature on the island and everything you need to know. Pump-out boat is very responsive. Everyone was very friendly. The launch is the only thing that will really get your attention, it is $5 per person each way. Not owned by same people. We took the dinghy.

Day 14 - Nantucket to Cuttyhunk. Again, our standard layover. Better current this way. It took less time than getting to Nantucket from the Vineyard and it was nearly twice as far.

Day 15 - Cuttyhunk to RI. This was the first day in two weeks that we saw seas over 2 feet. Some of those calm seas came with calm winds, but this day's were only 3 to 4 feet and occasional 5 feet. Reasonable seas with good wind to sail home on last leg.

All in all, we liked the Cutty, Vineyard, Nantucket tour much better than Eastern Long Island. We probably won't return to Gardiner Bay on Long Island anytime soon, but it was worth poking around.
 
#23 ·
Re: Cruise recap

Thanks to all for the help. We got home last night after two weeks out. Here's what we did.

Day 1 - provisioning in RI, helping friend ready his boat to join us around week 2.

Day 2 - RI to Dering Harbor on Shelter Island. Longest cruise up front to get things going. Head current for much of it, so it took nearly 10 hours of beating into the wind/current. Moorings were $95 per night!! It was worth a visit, but I doubt we'll go back. People were nice and friendly. Well protected cove, except for northerlies.

Day 3 - Stayed on mooring in Dering, but took the dinghy over to Greenport and toured around Sterling Harbor. Greenport is a nice little town worth visiting. The famous Prestons chandlery is a bit over rated, but still worth browsing. I can occupy myself in just about any chandlery or hardware store.

Day 4 - Shelter Island to Three Mile Harbor. Circumnavigated Shelter Island in 20 kt winds with gusts near 30. Current runs pretty strong on the south side near the ferry. We skipped Sag, as the winds were staying up all night and wanted more protection in the harbor and we've been to Sag before.

The harbor is huge, but you need to cruise to the western side to get any protection from prevailing wind.

Day 5 - stayed in the harbor for a night, just to relax. We walked to East Hampton for exercise (3 miles away, that's where the harbor got its name). We were not impressed. Its just showy, with little to be showy about.

Day 6 - Three Mile Harbor to Fisher's Island West Harbor. Expected light winds, but got 15 kts on the beam and rocketed to FI in two and a half hours. Anchored in West Harbor, which has plenty of room and great holding. Took dinghy to Yacht Club, which has a bad reputation for guests, but couldn't have been nicer to us. We asked if they had a transient slip available for the following two nights and they did. Fixed dock, but water and power were welcome at $3 per foot.

Day 7 and 8 - Stayed in slip at Fishers Island. Family took the ferry to meet us there, as we used to vacation on the island as kids. Ran around to see the old sights, BBQ, lobster, all the old traditions. Picked up my daughter and her friend to come with us for week two.

Day 9 - Fisher's Island to Cuttyhunk. Cutty is a very familiar place for us. Great stop over or day trip. We used it to rendezvous with a friend to flotilla for the next week.

Day 10 - Cuttyhunk to Edgartown (Martha's Vineyard). Great weather, but made a big mistake. Slept in at Cutty, went back in to town with kids, then decided to look up the current through Vineyard Sound. Right on the nose all afternoon and it can be a brutal 3 knots. No wind and we had to motor the whole way. It took over 5 hours. Again, met more friends on the Island and had dinner. Edgartown is a great harbor and the town has plenty to do. Wish we had stayed longer.

Day 11 - Edgartown to Nantucket - Another long day with little wind. Planned to get out in time for favorable current, but getting everyone going was slow and we hit it again. Not as bad as prior day and we have a three day mooring reservation, so we know we'll just kick back once we get there.

Day 12 and 13. Very relaxing time, saw July 4th fireworks from boat in mooring field. We thought they might be too far away, but they were great. The best place to watch is about a mile from the dinghy dock. The thought of walking back at 10 pm with all the crowds was unappealing.

I have to say that Nantucket offers a lot, if you can get there. Moorings were $75 per night, but seemed to be in very good condition, with adjustable anti-chafing. A skiff meets you in the channel and escorts you to your mooring. Then another comes along with literature on the island and everything you need to know. Pump-out boat is very responsive. Everyone was very friendly. The launch is the only thing that will really get your attention, it is $5 per person each way. Not owned by same people. We took the dinghy.

Day 14 - Nantucket to Cuttyhunk. Again, our standard layover. Better current this way. It took less time than getting to Nantucket from the Vineyard and it was nearly twice as far.

Day 15 - Cuttyhunk to RI. This was the first day in two weeks that we saw seas over 2 feet. Some of those calm seas came with calm winds, but this day's were only 3 to 4 feet and occasional 5 feet. Reasonable seas with good wind to sail home on last leg.

All in all, we liked the Cutty, Vineyard, Nantucket tour much better than Eastern Long Island. We probably won't return to Gardiner Bay on Long Island anytime soon, but it was worth poking around.
Excellent report, looks like you had a blast. Glad to hear that you had a good experience on Fisher's Island (I recently gave them a bad review but it was based on old information.) I'm just a stones throw away so maybe I need to get back out there...
 
#20 ·
Just spend 3 days at Coecles Harbor Marina (mooring rental $48/night for my Catalina 320 - $1.50/ft). Nice place! Beautiful, quiet. They have a nice pool, rent bikes and will shuttle you to town/ferry. They even rent electric cars!
Channel is shallow, but they provide navigiation tips on their website. We draw 4'10" and had no issues - Sounds like you it could be a challenge with a draft of 6'5", but you could give them a call.
Years back we spent time in Dering Harbor, on the other side of Coecles. Deeper water, but much more crowded mooring field - and services aren't as good, unless you are reciprical with SIYC. Same trip spent two days at Three Mile Harbor - Nice spot, but long walk into East Hampton.
Oh, and Rams Head Inn is no longer in business.
If you head this way, enjoy! It's a beautiful area to sail - just pay attention to tides/currents in and out of Gardiners Bay!
 
#21 ·
Backbeat said that Rams Head Inn is no longer in business. I was disappointed to hear that, so I called them today and they said they are certainly in business and have moorings on a first come first serve basis. I plan to sail over there early next week, and will report on how they are.
 
#22 ·
A report on Rams Head Inn: we sailed there yesterday, got one of their first come, first served moorings, dinghied to their dock and had a very nice lunch in a gorgeous setting overlooking Coecles Harbor. It was definitely open and excellent. Oddly, though, it was almost empty in peak season, albeit on a Monday.
I have also heard good things about Salt on Shelter Island, at Island Boat Yard. No lunch Monday, we will have to try that soon.
 
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