Summer is the time for playing around. For the vast majority of Long Islanders, ‘playing’ means doing something in or on the waters that, well, make us an island … no matter what the Supreme Court says.
[For those who missed it: for legal purposes, the court declared Long Island a peninsula on April 29, 1985. This could have resulted in things such as the Long Peninsular Rail Road, the Long Peninsula Power Authority, the Long Peninsula Expressway, etc. But I digress.]
Here are some spots to practice or partake in the various waterside activities that make Long Whatever such a neat place to live.
Windsurfing / Sailboarding / Kitesurfing
Put a sail and a surfboard together — or a kite and a snowboard — and you have sailboarding and kitesurfing respectively. What do you need? Flat water and high wind. Hands down the best spot for both these activities is Napeague Bay. Think of it as Long Island’s version of St. Marie de la Mere’s The Trench … only not manmade. Located on the north side of the Montauk strip (if you pass “Lunch,” you’ve gone too far), it’s essentially a land-locked lake (a small strait connects it with Gardiner’s Bay) that seems custom made for both sports. It’s relatively shallow, works great on the prevailing southwest winds, and rarely gets “chopped” out.
Upside: It rarely sports anything resembling a crowd.
Downside: Parking can be a pain in the butt.
Alternates: The east side of any tight-to-the-beach areas behind the many points jutting out into Peconic Bay.
Your favorite spot is relative. Montauk is — by far — “the” spot, but there are a variety of beach breaks all along the South Shore. And while anytime but summer is the best time for surfing, that doesn’t mean there aren’t waves in the summer. The area from Shinnecock Inlet and west to Tiana Beach offers the best variety of beach breaks that change nearly every season (and with the dredging of the inlet). It also seems to hold the mellowest, least territorial crowds — such as they are. If you can’t find a break at which to better your surfing skills, you’re just not walking far enough.
Upside: Miles of beach and zero crowds away from the town pavilions.
Downside: Problematic parking, but where there’s a will there’s a way.
Alternates: The South Shore.
Wakeboarding / Water Skiing
Like kite and sailboarding, you want flat water. Unlike the former you want really flat water and no wind. Long Island’s version of a Florida gator-pond can be found — if you have a boat and the tides are right — in, of all places, Port Jefferson Harbor. West of the harbor via a 200-yard tidal strip called, quite appropriately, The Narrows, is Conscience Bay. The bay shows up as a mudflat/grassland on nautical charts, so that should give you an idea of how shallow it can get. Regardless, this is the home for serious practitioners of being towed by a boat on the end of a rope. An alternate and smaller body of water in essentially the same locale is Little Bay, attached to the northwest side of Setauket Harbor, the entrance to which is south of The Narrows (which is sort of behind the west jetty of the harbor.
Upside: Landlocked flat water pretty much only used by skiers and boarders.
Downside: You really need to know what the tide is doing.
Alternate: You’ll be hard pressed to find somewhere that seemed so designed for tow-sports.
Like surfing on the Island, there’re a plethora of places to play Cousteau. If it’s beach dives, rather than boat drives, however, there are two Long Island classics: the Ponquogue Bridge in Hampton Bays and 67 Steps (or the Steps) in Greenport. The former is not for beginners; the latter is not for the physically unfit, because those 67 steps are about 1000 steps long after a dive — especially if you’re walking back up in full gear. Both are good night or day dives. The dive at Ponquogue is at the site of the now-gone wooden span. You literally will never know what you’ll see at this site. The tide is fierce, so you have to dive it at slack tide, but the visibility is excellent. Greenport doesn’t have quite the visibility of Ponquogue, but it more than makes up for it in bottom features; the place is littered with erratics (big rocks left behind by the glaciers) and other large-critter attracting bottom features.
Upside: Proximity to the dive at Ponquogue; Greenport … well, it’s a cool dive you have work for.
Downsides: Again, problematic parking.
This is an easy one for Long Islanders, and you have three major choices: Port Jefferson, Greenport, and Sag Harbor. What ties the three of them together? Well, historically they all had their shots at being “the” port of entry to New York and they were all “real” seafaring towns with histories rife in all things having to do with saltwater. They also all recreated themselves as harbor towns … not a far stretch. Drowned Meadow, nee, Port Jefferson, changed its name to honor the third president in 1836. Winter Harbor, then Stirling (for Lord Stirling), then Greenhill (as one word and two) became Greenport in 1831 (the village incorporated in 1838). The first mention of the Sag Harbor area goes back to 1698 (the first recorded mention by the name “Sag Harbor” was in 1709), but it was 1846 when it incorporated as Sag Harbor.
An excellent place to get the feel of Port Jeff’s early days is at the Mather House Museum, located on the site of shipbuilder John Mather’s 1860 home. A walking tour of the village’s historic streets must start here to get a true sense of the town.
To learn more about Greenport’s history, visit the East End Seaport Museum, at the ferry docks. A very nifty walking tour/guide can be found here.
And no trip to Sag Harbor is complete without a trip to the Sag Harbor Whaling & Historical Museum. The museum shop has a walking guide available.
BONUS: The East End's Best Surf Destinations