The summer season in Connecticut is revered, so make sure to book a trip between the high months of June and August to see the Sound come alive with boaters, bathers and paddle boarders.
The tide will gently shift the access to the water, but water fun is generally available whatever the weather. A fun day may include an early morning class tucked in close to the marsh where the water is slow and easy, then a BEC (Bacon, Egg and Cheese) and a good book in the sand.
Another option would be to board to troll along the coast, just watch out for rocks, boaters and the oyster beds. On your way out of Weed Beach try Bodega for tasty tacos and guacamole or 1020 Post for a few of those oysters you just paddled over.