With a surfeit of coast and water the East End offers boaters plenty of places to get away from it all, but here're our pick for the top 10 places to go with your boat to have fun or do nothing...and everything in between. These are listed east to west, and all are in the waters between the Forks...you'll want to try them all. So break out the charts (or the chartplotter) and sample the best the East End has to offer boaters.
Fort Pond Bay
This is actually an indentation of the north coast of the South Fork, so it's open to north winds (and Block Island Sound). Nonetheless, it's the site of the original Montauk fishing village, and allows divers access to the only underwater marine park on Long Island (in New York, for that matter). Cannons from the namesake ship (HMS Culloden; burned by the Brits to stop the ship from being taken after it ran aground) cover and uncover with the tides and storms, so you never know what you'll see. Look for the rock with the red paint up on the northeast side of the bay (hint: head 330 degrees off the rock, about 150 feet. If you go deeper than 25 feet, you probably missed the site). If the wind picks up, Lake Montauk and all it has to offer is right around the point.
Want a taste of a Pacific island (use your imagination!)? Try anchoring off private Gardiner's Island...anywhere, dependent on the wind, of course. There's great fishing (real flats fishing off the southern tip of the island), great scenery, great sailing, diving, beachcombing, etc. If it's getting away from it all you're looking for, Gardiner's Island is it. If sail- or kiteboarding is your game, head southeast for Napeague Harbor. You can't actually anchor in the harbor...access is definitely by dink or small boat...and on a rising tide, but since this area is virtually landlocked it gets flat water and good wind.
Three Mile Harbor
East Hampton's crown jewel can lay claim to the prettiest harbor on Long Island. The center of the harbor has good water, while the northwest side is relatively shallow. There are more than a half-dozen marinas stringing down the east side. Northwest through southwest provide beautiful undeveloped views. Sammy's Beach on the north is white sand fronting Gardiner's Bay and it's an easy bike ride/cab ride into East Hampton town.
A stay in Coecles is a must for island-tripping boaters. This is the spot on Shelter Island to raft up, solo anchor, you name it. Pick a section of the harbor, drop the hook and find your own piece of paradise. As quiet and charming as Shelter Island is, Coecles Harbor is even more so.
West Neck Bay
Enter through West Neck Harbor on the southwest side of Shelter Island and take the dinghy back into West Neck Bay. You'll slide past a unique winding creek of rarely-seen waterfront Long Island and enter an all but land-locked embayment - a waterskier's or wakeboarder's paradise. Gas up and lunch at the Island Boat Yard on the north side of the harbor before you leave. A nice — and oft overlooked — part of the Shelter Island experience.
Greenport Town Docks
Greenport's town-run Mitchell Park and Marina offers a beautiful new docking area, somewhat protected from the wind. There you find access to the reconditioned, indoor 1920s Herschell-Spillman carousel, a variety of eateries (some with their own docks), taverns and shopping. All combine to make this little town by the sea the success story it is. Hotels for those needing a break from the boat, marinas and chandleries up the kazoo, the railroad museum, the Shelter Island ferry, and access to clear, open-though-usually-busy waters make this a boaters must stop. Added plus: you never know what'll appear on the waterfront. From US Navy cruisers, to round-the-world tall ships, this deepwater-fronting-town will always surprise.
The north side of this private, relatively untouched island just off New Suffolk, sports a curving lowtide isthmus extending off the island proper that provides a private beach with deep water off its east side. Great for rafting-up, or just hanging out, it also provides a good spot for kite boarding, and the current — North Race — passing off the very tip of the beach is great for fishing.
Cold Spring Pond (et al)
One of the East End's you-didn't- know-it-was-there embayments — there are four neat ones running in this area just east of the Peconic-side opening to the Shinnecock Canal. Cold Spring is the first marked inlet east of the canal. Wiggle in and anchor up. Nothing to do, but kick back with your feet on the rail and mellow out.
Red Cedar Point
This point coming off the South Fork marks the entrance to Reeves Bay. Beware the unmarked bar running out towards the R4 buoy. Once around Red Cedar Point, you'll see all manner of vessels anchored up, some on their own pickup buoys. It can get a bit crowded (a relative word), but it's a more family-oriented anchorage and mostly protected from the summer southwesterlies. An alternative is north and a little west on the North Fork, on the west side of Simmons Point, but it's open to that afternoon wind.
Riverhead Town Docks
Okay, it's not a quiet anchorage, but it is overlooked. If you want to do something with the family besides bask and drool, try Riverhead. Tie up to the well-kept town docks (electric and water) and you can avail yourself of the Atlantis Marine World Aquarium, several eateries (including an ice cream parlor) and restaurants, nightly music (organized by the East End Arts Council) and who knows what else. Events like the Blues Festival draw a full house of boats that raft four wide off the docks; it's a carnival atmosphere. There's a gas dock right before the aquarium (Treasure Cove). (Note that the Route 105 Bridge has 25-foot clearance.)