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Discussion Starter #1
We're planning a summer cruise east on our Cape Dory Intrepid 9M. We've done a number of 2 day cruises to Sandy Hook, Peekskill & Bannerman's Island, Stamford, and Northport, but this will be our longest cruise by far. We're leaving July 10th and coming back the weekend of the 25th/26th.

Here is the plan so far, feedback would be great:
July 10-11: City Island or Port Washington to Coecles Harbor, Shelter Island - 80 NM, will do a modified Swedish Watch with Dog Leg, 6 crew on board total.

July 12-17: Move boat to Sag Harbor and stay the week until Friday. Anchor if possible with help of a local.

July 17: Sag Harbor to Montauk 23NM. Take a mooring at Montauk YC (pricey, unfortunately, but with shuttle into town and little other options, seems like best option). Meet more crew joining us via L.I.R.R. in Montauk town. Re-provision. Shuttles from MYC to-and-from Montauk town are hourly until 11pm.

July 18-20: Block Island, 20 NM, leave early Saturday morning to get a mooring or anchorage in Great Salt Pond before noon.

July 20, Monday: Block to MV, 60 NM, leave ~5AM or earlier. Shooting to get a mooring in Edgartown, but may gunkhole in Cuttyhunk if need-be.

July 20-24: MV, with possible overnight trip to Nantucket. Stay on mooring in Edgartown and explore island.

July 24, Friday: MV to Newport, leaving possibly from Vineyard Haven, 50 NM. Join with additional crew member/s in Newport Friday night.

July 25-26+: Newport to NYC, via Mystic, and possibly City Island or Port Washington
 

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I guess no one is paying attention to this forum these days as your post has been up a week and I, an infrequent visitor, am the first response.

First, I assume you have checked the tides and Eldridge.

I have never stayed in Port Washington, but it appears to be a nice place. Morris Yacht Club is right off the tip of City Island, has guest moorings, and is barely out of your way when heading up the Sound.

Coecles harbor is a beautiful spot. Very nice anchorage and nature preserve just inside the entrance. A good boatyard with a swimming pool at the far end of the harbor and not much else at all.

We stayed at Montauk YC for a night a couple of years ago. Can't say I recommend it. Not the best place for a good night rest as there were lots of big powerboats partying late into the night loud music and all. If it must be Montauk I would anchor and dingy or I believe there maybe a water taxi. Greenport is a really nice town and has a reasonably priced town marina with transient slips and plenty of dining and shopping options right there. Assuming there is train service I might have your friends meet you there. Other options that are a good meeting point, fairly easy to train from NYC, and an easy hop out to block are Mystic or Stonington, CT. Watch Hill, RI is a favorite stop of mine with a nice protected anchorage on one side of a mile long sand spit that has an ocean beach on the outside and a cute little town for dining, ice cream, etc. It has a long, somewhat dicey channel but is worth the effort.

Heading back to NYC, Old Saybrook at the mouth of the CT River is a possible stop with a couple of marina and the town of Essex, 6 miles up river has a lot of charm. The cruise up river is beautiful and there is a very nice anchorage called Hamburg Cove about a mile past Essex.

I have not been out to MV or Nantucket in a very long time. Perhaps someone else will chime in to help with you planning. Cuttyhunk is an excellent stopover if you need it. Sounds like it's going to be a great cruise!
 

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Discussion Starter #3
I guess no one is paying attention to this forum these days as your post has been up a week and I, an infrequent visitor, am the first response.

First, I assume you have checked the tides and Eldridge.

I have never stayed in Port Washington, but it appears to be a nice place. Morris Yacht Club is right off the tip of City Island, has guest moorings, and is barely out of your way when heading up the Sound.

Coecles harbor is a beautiful spot. Very nice anchorage and nature preserve just inside the entrance. A good boatyard with a swimming pool at the far end of the harbor and not much else at all.

We stayed at Montauk YC for a night a couple of years ago. Can't say I recommend it. Not the best place for a good night rest as there were lots of big powerboats partying late into the night loud music and all. If it must be Montauk I would anchor and dingy or I believe there maybe a water taxi. Greenport is a really nice town and has a reasonable town marina with plenty of dining and shopping options right there. and assuming there is train service I might have your friends meet you there. Other options that are a good meeting point, fairly easy to train from NYC, and an easy hop out to block are Mystic or Stonington, CT. Watch Hill RI is a favorite stop of mine with a nice protected anchorage on one side of a mile long sand spit that has an ocean beach on the outside and a cute little town for dining, ice cream, etc. It has a long, somewhat dicey channel but is worth the effort.

Heading back to NYC, Old Saybrook at the mouth of teh CT River is a possible stop with a couple of marina and the town of Essex, 6 miles up rove has a lot of charm. The cruise up the rive is beautiful and there is a very nice anchorage called Hamburg Cove about a mile up river from Essex.

I have not been out to MV or Nantucket in a very long time. Perhaps someone else will chime in to help with you planning. Cuttyhunk is a great stopover if you need it. Sounds like it's going to be a great cruise!

Thanks Cranki. We've stayed on a mooring in Port Washington before, the yellow ones are free for 24-hours. I race on a City Island-based boat that races in Manhasset Bay there, so I know it fairly well.

We are good on our current timing with current. We were going to try and stage the boat to the sound, either City Island or Port Washington, but the timing works out so we will leave around 12:30pm on Friday, making one brief stop at 2pm at a public access pier in Greenpoint, Brooklyn at the end of Manhattan Ave to pick up someone who doesn't get off work until 1pm.

Greenport may be a good alternative to Montauk, but I'd like to spend Friday night on the town in Montauk and I think most of the crew we are meeting there would prefer Montauk. I've been to Greenport a few times by land and I like it and the Long Island Railroad does go there, but not as frequently as the Montauk line, I believe. I added Montauk in there, instead of leaving straight from Sag Harbor, so we are closer to Block so we can arrive earlier on Saturday and make sure we get a mooring or good anchorage. The mooring at MYC is a bit expensive, but apparently the facilities are very nice and the shuttle into town is key for us. We'll have 6, possibly 7 on the boat for the Montauk to Block Island leg. We do have a perfectly functioning dinghy, so if anyone has a better idea, please chime in. From the reviews I have read on ActiveCaptain, there is not easy public dinghy access on the east side of Lake Montauk.

I've only heard good things about Old Saybrook, thank you for the recommendation!
 

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Crew of six on a 27 foot boat sounds a little crowded to me especially if the weather gets nasty. You do know that the weather may not be your friend. Don't be afraid to change plans rather than stick to your schedule. Also recommend having a Eldridge book on board and use the currents as much as possible.
That's a long slog from Port Washington to Coecles harbor especially when the current is against you. Personally, I'd do Port Washington to Port Jefferson to Mattituck to Coecles, Montauk or Sag Harbor. Taking advantage of a favoring current on all the legs.
 

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Your chances of getting a mooring at Block Island on a weekend in July are pretty slim. Most are taken early by those that arrived the night before and circled the mooring field in the AM looking for departing boats.

Overall your schedule is pretty aggressive and not something I would consider with just me and my wife. May be OK with a bunch of guys however
 

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Thank you everyone for the advice. The cruise went extremely smoothly. For the two-weeks-and-two-days we were gone, we only managed to have cumulatively a 3-4 hours total of rain. Here is what we ended up doing:

Day 1, July 10th. Left NYC at 2PM on Friday after picking people up in Greenpoint, Brooklyn and arrived Coecles Harbor, Shelter Island at around 12pm the next day, ~110 miles. No wind almost the whole way

Day 2. NYC-> Shelter Island Mooring at Coecles Harbor Marina

Day 3-7. Shelter Island -> Sag Harbor: Anchored outside of breakwater in Sag Harbor

Day 8. Sag -> Montauk: Picked up additional crew in Sag Harbor and sailed to Montauk. anchoring in Fort Pond Bay around 10pm.

Day 9-10. Montauk -> Block: Sat out storm that passed by (but almost no rain overhead) and left at noon for Block Island (Saturday). Harbormaster put us on a private mooring far away from the Boat Basin marina. Second day they put us on an open mooring closer in.

Day 11. Block -> Cuttyhunk: Monday, pick up additional crew who took ferry to Block from Montauk, leave for Cuttyhunk, anchor in the outer harbor area.

Day 12. Cuttyhunk -> Edgartown: Sail to Edgardtown through Quick's Hole, it's fairly full up and we're put on a yellow mooring in Edgartown off of Chappy. far from town.

Day 13. Edgartown -> Nantucket, beautiful day, sail most of the way.

Day 14. Nantucket -> Vineyard Haven. -- anchor just outside the mooring field, between the VHYC and the drawbridge/tank farm

Day 15. Vineyard Haven -> Newport -- we're put on a mooring in Brenton Cove. First time there by boat, crowded weekend--it's Newport Folk Festival weekend. Thunderstorm quickly passes while we are ashore. We take an Uber to-and-from the West Marine in Middletown, Uber was very cheap in Newport for both rides.

Day 16-17, July 25-26. Newport -> NYC. Leave Newport around 7am with a crew of 5. After light winds in the morning, sail entire way from Block Island Sound to Throggs Neck. Winds consistent in direction and strength. 10-15 knots S, SSE. Close reach turning into close hauled past Matinicock Point. We hit both Race Rock and the East River perfectly at max current. Use 4-on-4-off shift schedule. About 30 hours total, Newport to NYC.
 

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Sounds like a great trip. We sail that area, but I was off Sailnet for a while. Sounds like you certainly didn't need my advice.
 

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Discussion Starter #8
Thanks for the kind words. We did have a great time, and we do value any advice we get, especially from experienced cruisers in the area such as yourself. Our previous longest trip was just 2-days up the Hudson to Peekskill and Bannerman's Island/Castle and back. We've also done other overnight trips to Sandy Hook, Port Washington, and Northport, but this one took a lot of planning and guessing. It was our first time in most of these locations.
 

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Sounds like a great trip. If I had seen your thread earlier, I would have been happy to help, but I was out cruising then too.

Great to hear that Uber is a good deal in Newport. Taxis have always been extremely expensive. Newport to NYC is a long haul!
 
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Crew of six on a 27 foot boat sounds a little crowded to me especially if the weather gets nasty... Don't be afraid to change plans rather than stick to your schedule.
We actually has 7 for the first leg! But that was the overnight and we were sailing in shifts, so it was not too crowded for us. Once we got to Shelter Island, we had one crew leave so we were 6 on the mooring and that was the only time we were 6. I doubled-up in the quarter-berth with my girlfriend, which was fine. The next day we went to Sag Harbor and it was Sunday and 3 left so we dropped down to 3 for that evening. From Monday to Friday it was just me at anchor.

We were definitely ready to change plans. We waited out a storm before we left Montauk. My friend missed his ferry to Block Island on a Sunday and we had to meet him the next morning, delaying out departure to the early afternoon on Monday, so we anchored in Cuttyhunk on the way to MV. After we got to MV, we went to Nantucket the next day and that was not necessarily on the itinerary. Also, my original plan was to have a stop between Newport and NYC, but we did not stop, and I am glad we did not. It was 24-hours of great sailing.
 

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Newport to NYC is a long haul!
It was, but we had excellent consistent wind and it was a beautiful sail. We caught a Blue Fish near Race Rock and cooked it once we got home.

We are planning on going to Block again this week and we know it's going to be madness. The plan is to leave NYC Wednesday night and get to Block as early as possible on Friday morning.
 

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....We are planning on going to Block again this week and we know it's going to be madness....
You can say that again. Sounds like you were there in August, which would be just as mad. However, your notes suggest there was a bad storm, which may have kept the masses away (especially the stinkpotters). From this far out, the weekend looks pretty nice. Good luck.
 

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You can say that again. Sounds like you were there in August, which would be just as mad. However, your notes suggest there was a bad storm, which may have kept the masses away (especially the stinkpotters). From this far out, the weekend looks pretty nice. Good luck.
We were there on Saturday, July 18th through Monday July 20th. We probably did no arrive on Saturday until 4pm, and the storm was light but may have scarred off a number of weekenders.

We are going to move the boat up the East River to Port Washington tomorrow night, take a mooring, and then go straight from Port Washington through Thursday night to Block Island, about 100 NM. Hopefully we will beat all the other boaters who are leaving Friday morning from Narragansett Bay and other closer ports... we'll see.
 

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TyTy,
Congrats on your successful cruise. Hope your next Block experience is just as rewarding.

Your profile says you have an O'day 25', is this correct? Someone intimated you had a 27' foot boat. Am I confused? 6 or 7 for an overnight on an Oday 25' sounds "intimate" to me.

You can put your current boat make/model in your signature so it is easy for folks to figure out what boat you sail.
 

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Discussion Starter #17
We keep it in Morris Canal (Jersey City) at Liberty Harbor. The O'Day 25 was actually better for 6 people since the settee expanded to a double. We only had 7 on board on the Cape Dory when we were shift sailing overnight, so it was never crowded.
 

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And yes! It is a nice boat, we are very happy with it so far, much more robust and better for longer cruises than the O'Day
 
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