Richard,

It is considerably longer to go to Annapolis than Newport from New York Harbor. You will have to traverse the open coast of NJ and then the Delaware Bay, which can be nasty in the wrong conditions. The Chesapeake can be wonderful, but we enjoyed Long Island Sound very much, as well. Newport is a great place to visit by water, too.

Another thing - you really don't want to be in the Chesapeake in Aug if you can help it - way too hot and humid. For that time of year, Long Island and Newport will be crowded, but comfortable.

Just my 2 cents.

I grew up sailing on the Connecticut coast of Long Island Sound (Greenwich and Stamford) and taught in dinghies there for three summers in high school and college. It can be beautiful all summer long, but there are two things I would say about August:

1) It can be quite humid! I can't compare it to the Chesapeake, but August is my least favorite time of year to spend near New York

2) August can equal no wind. The boat I grew up sailing didn't have an engine (22 ft. daysailor), and the whole month can be calm to the point of disappointing. One year we had an intro sailing class where the school refunded all of the participants because for two weeks in mid-August there wasn't enough wind to learn. Again, don't know if heading south can be much better. And you CAN have days with great wind, it just isn't the norm.

If you do decide to take the Connecticut route, let me know -- I have a bunch of places I a can recommend stopping as you head up the coast.

I like Sandy Hook a lot and it's just a quick and scenic trip south of NYC. Then cutting east (if the wind is decent) would take you outside Long Island to Block Island (a must see). Then you could return through the sound for a memorable trip through Hells Gate and the East River. There are many beautiful places to see and they are relatively close compared to the long haul to the Chesapeake.

My feeling is that Newport, Oregon and points North would be the best possible choice. However, it sounds like your schedule wouldn't permit a Panama Canal transit at this time. Maybe someday.

In reference to Kevin's comment, we live on Sandy Hook Bay and sail out of the local harbor.

If you do decide to take the route Kevin suggests, be aware that there are not a lot of places to duck into on the eastern shore of Long Island. It's generally considered to be about a 26 hour sail from Sandy Hook to Block Is. and you can get a wind against the current rounding the tip of LI.

People here do it all the time but many (us included) prefer the "inside" trip up the East River and thru LI Sound. Lots of places to stop and, if you want to go straight through to Block, it doesn't take much longer but you have the safety of a lot of safe harbors should you need one. Plus, if your not used to sailing up the East River, the view never fails to impress so one trip thru it isn't enough anyway.

I should add that you don't "sail" up the East River,... it's a power WITH the current... two hours after low at the Battery going up and two hours after high water coming south.

Chuck's excellent comments reminds me that you really need to have the Eldridge Tide and Pilot book for the year you go. Maybe there are alternative references out there, but you do not want to attempt passage through certain areas (East River through Hell Gate is one) unless you are going with the current. Eldridge does a great job of giving you the info you need.

Another comment is when approaching Roosevelt Island from the south, you need to be on the left (W) side of the island to avoid a 34 foot bridge that only opens with many hours of advanced notice and you just don't want to do that. If you got to that bridge with 3 knots of fair current, and realized late it was a short bridge, it would be a difficult time turning around and retracing your steps.

This is all a fantastic place to visit while cruising, but get the right resources and plan your passages carefully.

Eldridge is great, but the NOAA tide and current web pages are even more detailed!

Joe...

web pages are great, but being a luddite, I like a book I can keep looking back at.