Love to Surf or Sail? You’ll Find Both in the Hamptons

The biggest draw to the 118-mile-long South Fork, or Hamptons, on the east end of Long Island has always been its prime waterfront location. Generously wide swaths of sand trim the Atlantic coastline side, which is wild with waves, making it ideal for swimmers and surfers alike. There is also the bay side dotted with marinas and low-key beaches, appealing to boaters and sunbathers preferring a more mellow beach day.

The water-rich setting offers something for everyone. “In the Hamptons you’re surrounded by beautiful beaches, great waves, decent winds and a ton of water sports,” said Susan Breitenbach of the Corcoran Group.

Sun seekers have their pick of incredible beaches with varying amenities, such as snack bars, picnic table and grilling areas. Some, but not all, have lifeguards. Many of the town-maintained beaches require parking passes (for residents and non-residents) which can be purchased in advance through the specific town hall beginning in February.

For those looking to catch some waves, riders of all levels can be found paddling out from Westhampton to the tip of Montauk. Popular surf breaks include Ponquogue Beach in Hampton Bays, Coopers Beach in Southampton, Main Beach in East Hampton and Ditch Plains in Montauk. If interested in learning to hang 10, private and group lessons are offered at the Flying Point Surf School or Hampton Surf Co. (and you can take to the water year round). Kite-surfing and stand-up paddle boarding are also popular ways to ride the waves.

As for the boating set, they can be found at area marinas and sailing clubs during the season, which is generally April through October. Ms. Breitenbach notes private, members-only clubs such as the Sag Harbor Yacht Club and Breakwater Yacht Club also in Sag Harbor are popular among summer locals. The handful of area clubs host regattas, sailing lessons, sailing camps for kids and have boathouses and instruction for those serious about getting out on the water. Memberships vary from club to club, but expect a waiting list.

The same is true for the area marinas, advised Beau Campsey of the Sag Harbor Cove Yacht Club, which is a public marina with slips, fuel docks and the Beacon restaurant. Although public, slots fill up quickly by returning area boaters. “It’s easy to buy a boat, it’s getting a slip in Sag Harbor that’s the hard part,” Mr. Campsey said. He notes that people with yachts do tie up at area marinas, but it’s more common for yacht owners to have private slips on their waterfront properties.

Waiting lists for area marinas are a year-long on average, and the cost for a slip for a 50- to 60-foot boat for a season can be around $40,000.

"The Hamptons are as great for a megayacht as they are for a small fishing boat if you want to sail out to Shelter Island,” Ms. Breitenbach said. “That's why we have boating enthusiasts like Jimmy Buffet and Christie Brinkley here.” Other notable residents, including Billy Joel and Jerry Seinfeld, are often captured by the paparazzi boating around the area.

The picturesque marinas are packed with boats in high season, and private clubs are the place to be.

“One of the best-kept secrets for sailing clubs is the Sag Harbor Yacht Club located right in Sag Harbor village. It has been around since 1899, and every year they host the fireworks on the 4th of July weekend. It’s easy to dock at the marina, fuel up, or stay the night and walk to town for dinner,” Mr. Burnside said. The Montauk Yacht Club and Breakwater Yacht Club are also popular with locals.

Boating and surfing events are a large part of the social scene in the summer. You might catch a glimpse of professional surfer Kelly Slater at the Rell Sunn Longboard Championship in Montauk every August, or A Walk On Water in Montauk in September, a surf-therapy event that teaches the sport to children with disabilities.

“The sailing races on Wednesday nights in Sag Harbor are one of my favorites,” Mr. Burnside said. “Sailboats ranging from 20 to 45 feet are informally sponsored by the Breakwater Yacht Club and last through October.”