Too many places to name...
It's hard to say without knowing how far you want to go...Here are some thoughts, I could write a book.You can't beat SoNo (South Norwalk) for the best restaurant/bistro strip in the state that's withing walking distance of marinas. There's an IMax theater, an aquarium. Nice place, short sail from Huntington.Captain's Cove in Bridgeport (yes, Bridgeport) is very cool, a fun happenin place. Mix of boating families, 20-somethings on the lookout for Mr/Ms right, and adults coming by after work.New Haven: I lived there for years, and there are good--no, superb--restaurants and one decent marina, but visitors trying to walk around can stumble into some mean streets way too easily. The taxi is 777-7777 if you decide to stop there, call a cab. I don't really recommend it for newbies.Madison and Guilford are very cool towns to visit, but don't have much of a waterfront. Duh. That's the story of Connecticut's life.Good anchorage: Duck Island (my home harbor). Good overnight stop with plenty of room, good holding and reasonable shelter. It's a looooong dinghy ride to shore, however. If you decide to brave the dink ride, try the Boom restaurant at Pilot's point. Come by for a visit, I am South Yard L6.Old Saybrook. Every week the CT TV stations run a Sunday night news story of two boats with drunk operators colliding and bursting into flames in the mouth of the CT river. I'd stay out of there.New London: A cool town with tons of potential, in about 10 more years it'll be safe for anyone to walk around there at night. Cheap moorings by Shaw's cove that nobody knows about. Giant Ferries.Mystic: The second-best boating destination on the east coast (Newport is #1) IMHO. Call ahead for a slip, though. Gets crowded.I'd recommend buying the Maptech or similar guide. Good exploring.Paul