Be sure to consult Eldridges for the tide charts when planning your trip. Never try to fight the tide near the race, unless you want to spend hours observing Plum Island. Also note that the current inside and outside of Long Sand Shoal can be moving in opposite directions, less than 2 miles apart!
Moving to the east on the Long Island side is Port Jefferson (18nm away). As you enter the harbor, to the right is an unnamed bay which is highly popular with sailors.
My father called it Conscience Bay, and we probably anchored there 1,000 times (or so it seems) in my youth. Given the prevailing SW breezes, it’s usually a nice reach to and from Norwalk. Takes 3-4 hours in a 36 footer, 4-5 hours in an under 30 boat generally. You can also go into the town at the head of the harbor and pick up a mooring or dock. Danforth’s Restraint is popular. The sand pit, to your port as you pull in, has some shallow spots (I spent one afternoon on one after the boat swung around). The winds are shifty. Best left to the motorboats that crowd in, but it is fun for kids to climb and play on the cliff’s. Anchor just outside the sand pit.
After Port Jeff, the next harbor is Mattatuck (38 nm away), a narrow creek with only about 5 feet of water on low tide. There is a little room to anchor at the head of the harbor. Well protected, but nothing great.
The Connecticut side has many great harbors. From Norwalk, the first harbor is beautiful Southport (6nm away). No room to anchor, and only about 6′ in the outer channel at low tide. Call the yacht club for a mooring.
Next is Bridgeport (12 nm away). There is plenty of room behind the breakwater, and Pleasure Beach really is nice, but few boats stop here except for Tugs. I have spent a few nights in Bridgeport, and if nothing else, it sure is easy to enter in the dark due to all the lights. Bridgeport is getting better, with the baseball stadium and new marina planned, and it will become a better destination in time.
Black Rock, just to the east of Bridgeport Harbor, there are lots of little shops in Captain Cove Marina. Sort of a mini Mystic Seaport. Great yard, nice people. Stay away if the breeze does not have a westerly component, due to the treatment plant to the east.
After Bridgeport is Milford Harbor (no room to anchor, not too much to do), and little Charles Island (18 nm away), which you can anchor behind. Often crowded with day trippers, not many overnighters.
After the New Haven breakwater (not as good a stop as Bridgeport, but ok), comes my favorite spot on the Sound, the Thimble Islands (30 nm away). The Thimbles are huge hunks of Granite, and look like a chunk of Maine dropped in the Sound.
There is good holding ground in the mud between the islands. Stay away from the marked power cables. Enter in the daytime. There are numerous confusing buoys marking the many reefs. Once your in, it’s beautiful, if you like Maine. Unfortunately, the islands are all privately owned, so no exploring.
Adjacent to the Thimbles is Branford Harbor to the east, and Sachems Head to the West. Given the numerous reefs in the area, plot your courses carefully in advance, watch the depth like a hawk, and use lots of compass bearing to check your location. GPS is useless for threading around the reefs and islands. Sachems Head has a fine yacht club, but no space to anchor. There is plenty of space in the large harbor north of Sachems head, which is the place to go if the Thimbles are full up.
Past the Thimbles is Guilford, which is one of the prettiest town greens in Connecticut, a short 10 minute walk from the harbor. Unfortunately, the channel only carries about 4′ at low tide.
After Guilford, there is Westbrook and Duck Island Roads, which has a breakwater with 6-9 foot depths to anchor behind. Fairly exposed, lots of tide. I prefer to head up to Old Saybrook, and stay at the Dock N Dine (50nm from Norwalk).
Given the two lighthouses and prominent breakwater at the mouth of the Connecticut River, it’s an easy nighttime approach. If you grab dinner (or pull in between midnight and 11:00 in the morning), there is no charge to lie alongside the pier. Great spot to switch crews or pick someone up. Next door is a beautiful and very expensive resort marina, with a very good restaurant.
Five miles up the river is Essex, with a fine downtown and the great Griswold restraint. The Gris has one of the finest collection of ships prints in the country, worth more than the restraint. Stay at the Essex Island marina.
Four nm up is the beautiful fresh-water Hamburg’s Cove, and three more miles up is Gillette Castle. Another three miles and you’re at the Goodspeed Opera House, which is right on the river, with a pier. Probably can tie up, call ahead.
After the Connecticut River, the next great spot is Mystic, with the world renown Mystic Seaport. The bridge into Mystic only opens a few times a day, so get the opening times in advance.
It’s wonderful to stay one or two nights and be able to walk the grounds after everyone else has left. If you are a member, the dockage is a pretty good deal. You can also walk north to the Mystic Aquarium, or south to town, both of which are worthwhile.
There are also some Islands off Noank that you can anchor behind. After Mystic, Stonington and Fishers Island are a few miles away. Fishers Island offers beautiful estates, and not much else. I’ve anchored in both the west and east harbors in the J44, but neither are especially deep.
Stonington is also lovely, and Dodson’s boatyard is as nice as they come. Another great spot to do crew transfers. The downtown is beautiful, lots of antique houses and great dining establishments.
Through Plums Gut, Long Island begins to get interesting, with Shelter Island a wonderful spot, although I normally hurry on through the Race or Watch Hill Passage to Block Island. Block Island is a great destination, truly out to sea, with enough to do to keep everyone happy. The biking and hiking trails are great, plenty of good restaurants, super beaches, etc. Try to stay a few days if possible.
Everyone knows Newport, but Narragansett Bay offers a vast selection of Harbors, Jamestown, East Greenwich, Wickford, Bristol (visit the Herrshoff Museum), and the Kickamuitt River, where I spent a Hurricane a few years ago. All fine cruising grounds.