While the Chessy does not need a hard sell I've got to say that Dave's sailing area (back yard) is nothing like the LI Sound. It is a lot bigger with great anchorages all over. It is also a lot shallower (in terms of water depths) and much more unspoiled then a lot of LI Sound's bays and harbors, especially the eastern shore. Anchoring out is usually easy and there are marinas for when you want accommodations and a restaurant instead of home cooking.
The light airs of summer (July/August) would also be a good time for using a spinnaker or asym. There is much less current in the Chessy then the LI Sound and if you are going to run aground somewhere it would be in the Chessy where the bottom is shallow but mostly sand or soft mud. Recent charts and common sense will help keep you from grounding though.
If you like seeing Ospreys and Bald Eagles among the throng of other shore birds you will enjoy the Chessy. I've seen sting rays mating and dolphins are sometimes seen in the southern Bay near the mouth of the ocean; I have not seen this yet though.
For the past 3 or 4 years I've had the privilege of being able to get down to a friends 32' sailboat for 2 long weekends each year. I always enjoy it and get to see new anchorages and places nearly every visit. I grew up sailing on the LI Sound and still love it but the Chessy is a special place.
Hope you like crabs (the kind you can eat that is).
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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