A person I know asked me for suggestions about how to cruise around
Long Island, just east of New York City, NY, USA.

My wife and I have done that trip 5 times now because it allows us to
leave the boat and get back home (to work) easily.

Here are my favorite cruising destinations near NYC and Long Island.
I hope you approve of my ranting on this subject.

Obviously you use this information at your own risk, as the cruising
guidebooks say

The trips which include the NYC East River and The Race at Orient
Point need to be based on the tide tables of those specific transit
days. Get an up to date Eldridge Tide Tables book and read it
carefully for those two transits.

Notable destinations you may want to consider (you can't do all of
these in 1 or 2 weeks, so they become alternatives if you don't have
more time)

Greenport (3 out of 3 stars) if you stay at the Town Dock (expensive),
Claudio's (expensive), or S.T. Preston's (best deal if you can get it
- no reservations). Nice moorings (inexpensive and the Harbor Master
doesn't come all the time so you might get a free night) in Stirling
Harbor, but you need a dinghy and a walk to get to town.

3 Mile Harbor (2 stars)

Sag Harbor (3) has moorings, anchorage (less protected) and dock
slips. 3+ stars if you stay at the Waterfront Marina and are across
the dock from the mega yachts

Block Island (3+) anchorage or mooring in New Harbor, maybe 4 stars if
you stay at Champlain's Marina where you will be rafted up to other
sailboats

Montauk Harbor (2)

Shinnecock Bay (2)

Sore Thumb anchorage in Fire Island Inlet (2) from here you could
stay inside the State Channel to the East Rockaway Inlet, but it's a
longer trip that way and you have to wait for draw bridges along the
way
if you do want to consider an 'inside' trip, let me know because there
are numerous anchorages and marinas along the way

Sheepshead Bay mooring in Brooklyn (2)

City Island mooring (2)

Manhasset Bay mooring (3) there are a small number of free moorings
if you get there early enough; check the cruising guide

Oyster Bay mooring or anchor in the sheltered northeast corner all the
way on the inside of West Harbor (2)

Cold Spring Harbor mooring or anchor (2)

Llyod Harbor anchor (1)
or Northport Bay anchor (1) or Northport Yacht Club mooring which
includes use of pool (2) or free tie-up all day at the Northport Town
Dock (3)
or Huntington Bay mooring (2)

Port Jefferson mooring or anchor (3)

Mattituck Inlet anchorage near south end (3)

If you get the urge to spend some time near Manhattan

79th Street Marina (a NYC Parks Department property) would be 3 stars
but there are so many boat waves during the day that it gets 2 stars

Liberty Landing Marina in NJ is 2-3 stars because it is well protected
from boat waves but you're not in Manhattan

for people with very deep pockets financially there are other NYC
marinas that can get you easy access to Manhattan with varying degree
of success in avoiding the daytime boat waves

You can anchor in New York Harbor for an excellent view of the 4th of
July fireworks there.

3 stars means that you can easily get from your boat to the downtown.
Keep in mind that I have a motorized dinghy onboard, so being anchored
means I don't need a mooring launch boat to get me to/from the
downtown area.

2 stars means not as easy to get from you boat to a nice downtown
area. For example, 3 Mile Harbor is a lovely destination if you're
willing to stay onboard. But if you have a dinghy you can get a taxi
ride to town. I like to give my wife something else to do when we go
boating, so a visit to a downtown area is a nice change from sitting
on the boat.

1 star I don't even consider a destination

Of course you will want to make reservations well in advance during
the peak season around the 4th of July and August.

And all this rambling doesn't even touch the south shore of CT or the
north end of NJ or the south shore or RI or MA.... Or the multiple
harbors available at Shelter Island.

If you haven't done it yet, someday you have to do 4th of July in Oak
Bluffs, Martha Vineyard and make sure you see the lighted houses of
the 'campground' neighborhood along with the fireworks at their Ocean
Park. Easily one of the all-time best destinations for 4th of July
fans. Their Ocean Park has a lovely old-fashioned gazebo in which the
band plays and the locals dance around the gazebo in a big dance line,
almost like you would expect them to be roller skating. Try to stay
at the Oak Bluffs Harbor Marina if you want to have immediate access
to their wonderful downtown which includes an authentic old fashioned
merry-go-round. This one gets 4 stars out of 3!

My all-time favorite nearby destinations are Greenport and Sag Harbor.
Further away I would add Oak Bluffs and Nantucket.

We are so blessed to be able to be boating with such wonderful
destinations near NYC!

I encourage you to consider taking the time to enjoy the destinations
along the way. Try to find places to leave your sailboat so you can do
a 'progressive vacation', in which you go as far as you can with your
boat until your vacation time runs out. Then find someplace nearby
where you can leave your sailboat on a mooring, go back to work for
the week, then return to the sailboat the next weekend and move a
little further along the way via other week-day moorings. The Long
Island north shore is best for that, so you could consider starting
your trip by running along the Long Island south shore first (assuming
good weather). You can get moorings starting at Sheepshead Bay and
almost all the other north shore destinations I've listed including
City Island - but the 4th of July timeframe is popular so make
reservations early.

=== more ranting ===
As long as I'm ranting about my favorite destinations in the area,
here are some additional wonderful nearby destinations:

Thimble Islands, south shore of CT, in Branford Town. 3 stars out of 3
for scenery, but no downtown. Large rocks like you would expect to
see in Maine and they have a house or two on them. It is possible to
anchor in here, and people make this a vacation destination.

Mystic Seaport, 4 stars out of 3 if you stay overnight in the Mystic
Seaport Museum. A wonderful town, too.

Newport Harbor 4 stars out of 3 as long as you have easy access to the
wonderful downtown.

Red Bank NJ and the Navesink River 4 stars out of 3 if you spend some
time in the wonderful downtown area and browse some of the (too many)
antique shops. Be careful getting in and out - it's not for deep draft
boats. We need 4'9" and got grounded at mid-tide. Keep your Tow Boat
US insurance up to full coverage.

Essex CT and the Connecticut River are 4 stars out of 3, since the
River is easily one of the most beautiful places to go boating in the
area. The Mattituck River in Long Island is a close 2nd place. If
you go, make a side trip to visit Gillette Castle and Hamburg Cove.
Hamburg Cove is beautiful and has moorings.

Watch Hill Cove is lovely for a short stay, 3 stars.

On Sat, 10 Jan 2009 18:27:40 -0800 (PST), wrote:

A person I know asked me for suggestions about how to cruise around
Long Island, just east of New York City, NY, USA.

You left out some pretty interesting towns and harbors on the north
side of LIS such as Greenwich, Stamford, Norwalk and the islands,
Stratford, Milford, Branford, Noank, New Rochelle, Larchmont,
Mamaroneck, etc.

Block Island, Newport and Pt Jefferson deserve more information.