“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.”