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Gardners Bay, Including Greenport, Shelter Island and Montauk
Plum Gut: If you want to go into Gardiners Bay from the west, you have to transit Plum Gut, the narrow opening between Orient Point and Plum Island. Wicked current, so this is another passage that has to be timed to suit the currents. The idea is to go through at the end of the eastbound ebb so you can pick up the ensuing westbound flood toward Greenport or Sag Harbor. Coming from the east (Block Island) or north (Fisher's Island Sound), you can go in behind Little Gull Island, but if the current is westbound, you'll have to bear off considerably to the south because the current is actually setting to the northwest and will be pushing you back toward the Gulls and Plum Island.
Orient by the Sea: This is a little marina around the corner from Orient Point and just west of the New London and Department of Agriculture ferry docks. Only a few slips, but it has a good restaurant for a place that's in the middle of nowhere and good swimming off the adjacent beaches to the west. Go in/out at half tide or better if you draw over four feet.
Orient Harbor: A great spot to anchor, but can be bumpy if the prevailing southwest wind blows all night. Small yacht club at the east end.
Greenport: Unlike the upscale towns on the South Fork, Greenport is a working fishing and boat building town. Best place to stay is at the marina associated with Townsend Manor. Has pool and Laundromat, but it's gotten pricey since the mid-90s. Hang a right after clearing the breakwater and run parallel to it into Sterling Harbor. The Manor is at the start of the left fork of the harbor across the creek from the hospital. Brewer's is on the opposite shore. The advantage of Townsend's is that you can walk into town. Brewer's has a courtsey van that goes to town, but check to see when the last run back is--taxi service in Greenport is spotty. Instead of going into Sterling Harbor, you could dock at Claudio's on the waterfront itself, but it's busy and bouncy, and you'll be a tourist attraction. Preston's is the major chandler. Greenport is one of the few harbor towns that has a movie theater right in town instead at some distant mall. (Northport and Sag Harbor are others). Best place to eat is the Rumb Line--guess what the various big boat parts that hang from the ceiling are. An alternative is the Chowder Pot Pub, which is on the west side of town across the street from the LIRR station. The liquor stores in town carry wines from the local North Fork vineyards. The chardonnays and merlots are the best outside California.
Dering Harbor: This harbor is opposite Greenport on Shelter Island. There's a marina and the Shelter Island YC, which runs hot and cold with respect to CYC members.
Sag Harbor: OK because it's not a real South Fork town like Easthampton. A nice day's sail from Greenport is to catch the current going west into Little Peconic Bay, hang out there until the current goes east, and then go around the south side of Shelter Island into Sag Harbor. On both sides, leave plenty of room for the little ferries to maneuver in the current. In Sag Harbor, call up the harbormaster on VHF channel 9 to check on availability at the municipal marina or go to the Yacht Club just beyond it. The YC is the more expensive, and the private marina adjacent to the municipal marina to the north is very expensive. Both there and at the Yacht Club the megayachts will block your view and the breeze. The local theater features Broadway casts because so many actors and actresses summer in the Hamptons. The whaling museum is worth a visit. If you think you've had rough passages, read some of the personal logs.
West Harbor: If you want to anchor out instead of going into Sag Harbor, there's a beautiful little harbor on the southeast corner of Shelter Island, just west of the ferry crossing. If it's low tide, hug the red just inside the entrance. There's a designated anchorage in the southeast corner marked by buoys. The Shelter Island side of the route into Sag Harbor offers a number of other quiet anchorages that are protected from the west.
Coecle's Harbor: Another protected and picturesque harbor, this one is on the north side of Shelter Island. Also a bit shallow. The marina will provide transportation to town for dinner.
Three Mile Harbor: East of Sag Harbor on the South Fork. One of the restaurants that caters to the marinas just inside the entrance has a fully rigged 5.5 Meter that sailed in the 1954 Olympics behind the bar. The owner claims he can have it sailing in a week. Look for the restaurant with the tall cupola. There are restaurants and a movie theater in East Hampton, which is a short cab ride from any of the marinas.
Montauk Pond: Mostly for shark fishermen. Good place to anchor out and buy fresh fish, though.
Cruising - East along the Connecticut Shore
Cruising - Block Island
Cruising - Rhode Island East to Marthas Vinyard and North to Salem
Cruising - West Along the North Shore of Long Island
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