[QUOTE=jmcelwee;21861]Hi all,

I'm plotting out a 16 day cruise from RI (East Greenwich) to NYC via Long Island Sound. Hoped to get some advice from the boards:

1. Would the winds/weather likely be better in June (beginning) or July (middle)? Those are my two vacation windows, so trying to pick one.

2. Do you think 16 days is sufficient to cruise there and back? I'm happy doing 1 or 2 long overnight sails to put some miles under the keel, but want to make sure I'm not biting off more than I should.

3. Any particularly lovely/fun ports to visit on the way?

Thanks!
-Josh[/QUOTE]

We've transited the LIS half a dozen times, and never had much sailing - either no or contrary wind. The caveat is that these trips were generally at the beginning or end of the season (i.e., bringing the boat to or from winter layup), so can't really vouch on the winds in June or July. Always done it in 2 legs/days; from East Greenwich you could do it very comfortably in 3.

Favorite stopping places for us on the LIS, thus far: On Long Island: Mattituck (tricky depths, but we've managed with our fin keel), Mt. Sinai, Port Washington.
In Ct: Milford

There's also, along the way for you, various nice stops in Fishers' Sound (Watch Hill RI, Stonington and Mystic CT); or, in Gardiner's Bay between the forks of LI, you could duck into Coecle's Harbor on Shelter Island or Three Mile Harbor and then enter the LIS via Plum Gut at Orient Pt.

Eldridge's Tide and Pilot book is very handy for this trip in terms of planning out how to make good use of (or not be stymied by) the currents, particularly at either end (the Race and Hell Gate/East River).

I lived in Connecticut for 54 years and sailed Long Island Sound for forty years. In June and July the winds are usually a pleasant S/W breeze. When it rains the wind moves to N/W and is gusty 10/20. Remember the Sound is primarily east and west not north and south.

One thing you have to be careful of is going from L.I. Sound into the East River via Hell Gate. The currant is as much as 6 knts and sometimes stronger. If you motor with the currant you will be going around ten knots. If you are trying to go against the currant you will be practically standing still. So consult a tide and currant chart to plan your trip through Hell Gate. You will find a similar problem entering the other end of the Sound, but not as bad. Again check a tide and currant chart.

Keep in mind that the tide changes are over six feet so if you tie up to a fixed dock at high tide and come back a low tide your sailboat will be six feet lower. Check you paper charts for sand bars, rocks and breakwaters that are only visible at low tide. Don't depend on a chart plotter because some of them do not show these hazards.

Aside from the two ends of the Sound you will find a pleasant sail with some nice anchorages and a few nice marinas listed in a cruising guide.

You might add Oyster Bay Marine on your stops. It is a well protected harbor with loads of places to anchor, or moorings available. Launch service runs early to late, with good size boats. In town there are family restaurants to upscale, and a carvel. Teddy Roosevelt park is across from OBMC with swings and a picnic area. A cab ride to Teddy Roosevelts summer home, just check, they were closed for renevations.
Also I do quick overnights or rest during tide changes (you do want to ride the tide for East or West bound headings) with a quick drop the hook inside Port Jefferson Harbor, or Lloyds neck on the West side just before the lighthouse entering Huntinton Harbor.

Been there done that at night, alone or with crew. Will do it again. Sometimes to catch the tide you just gotta get up at a strange time and power out. Usually winds are dead at night, if your lucky you get a following wind. Remember wind against current is a bad combo. You must watch for lobster pots. Hadn't caught one in 10 years, and hit two in one day. Most boat traffic is gone at night, but barges will sneak up.

  So keep your eyes open, your radio available to hail, and glance at the radar. I saw a huge reflection off a bouy, which in fact turned out to be a barge. No speed cylinders while on watch, and you should be safe, no reason not to travel. Most traffic is well lit, but may blend into the shoreline, especially on the western Connecticut side. Cant say your better on the Northern or Southern shore, I play the center or sides to get the most favorable current. Look at Eldridge maps, they are good.

Sailed out of Milford, CT for 15 years, now in Wickford, RI.  16 days is plenty of time. Suggest Block Island, then outside Fisher's Island to Mystic, then Milford, then Norwalk or Oyster Bay.  From there, Hells Gate at slack, down the East River with the Manhattan skyline to starboard, round the The Battery, and take a slip at Liberty Landing. There's a ferry right there that will take you across the Hudson River to the World Trade Center to explore Manhattan, USS Intrepid, museums, etc. Passing under the Verrazano, you can return on the Atlantic side of Long Island just staying a few miles off, which is a wonderful and safe night run, ending up at Montauk. From there if you have time you can explore the Whale's Tail (the east end of LI) and then make your way north back to Narragansett Bay, just a day sail from Plum Gut.

The further south you go, generally the less wind. Most big traffic in LI sound keeps on the south edge (NY). Use Eldridge tide book (yellow).

I grew up sailing on LI Sound and way back when was on the water every day for 3 summers worked as a sailing instructor in Greenwich, CT). A given weekend in early June is slightly more likely to give you better wind than mid-July, but both are much better than August. If you really want *hot*, July is better; early June will be quite warm but unlikely (always possible though) to be above 80-85 degrees.

I can tell you that statistically, wind is equally likely to be E or NW in June; by July prevailing winds are more frequently northwest.

If you haven't seen it yet, Windfinder Wind/Weather statistics are awesome for this. Make sure you click the "wind statistics" tab on the link below:
http://www.windfinder.com/windstatistics/western_long_island_sound

Sounds like I'm the reverse of you -- started many years ago on LI sound, and now am in the PNW!