Norwalk and its Islands are nice
Its probably a 3 hour sail from Port Jeff. You could anchor amongst the islands and have lunch and explore. Have good charts and keep an eye on where you are going - local knowledge helps in this place as I have seen boats go in places I am not sure the charts would encorage me to go . If you like a little bit of partying and nice restaurants the town dock is right over the bridge from Washington Ave. later in the week & weekends the most is going on (Martini Bars, Bands, nightlife, all sorts of restaurants -- cool shops to browse through). Also if you have kids there is a good Aquarium right down the street -- all worth while. But I would stay in the town dock as its not easy to find anchoring in the small mooring field they have next to the town. Its probably ~ $0.50 a foot to tie up for part of the day and maybe $1 (or a ($1.50???) to stay over night, -- sorry no electricity, though they do have a pumpout and running water, but the town dockmaster is very nice and accommodating. Note: Weekends during the day are very busy and tougher to find/get a spot until maybe later in the evening, but its doable.Annapolis is very nice and I think Mystic, Newport and Norwalk are probably the only places that hold any resemblance to Annapolis though (as you know) there are very many nices to stop all over the LI Sound