Because the surfing is so good, and because it’s so close to Manhattan (three hours by car or train), Montauk can be a madhouse in the summer. But come September, the lineup thins out, the town reverts to its sleepy fishing-village roots, and hurricane season brings the prospect of ten-foot waves. Stock up on surf supplies at Air and Speed Surf Shop on the main drag. For lodging, book a room with Rob McKinley, who co-owns the Surf Lodge (from $450 a night; thesurflodge.com) and this summer opened Ruschmeyer’s hotel (from $425 a night; visitruschmeyers.com). While the former is all surf, all the time—surf movies on large screens in the lobby, surf art on the walls, and a 1982 Swiss Pinzgauer jeep that shuttles guests between the lodge and the beach—McKinley, 35, describes the latter as “nautical camp for adults.” Spread out over a wooded lakeside property, Ruschmeyer’s is reminiscent of Dirty Dancing, with an on-site tepee and a Ping-Pong table in the outdoor sand-filled beer garden.
On Rob: Shadow plaid button-up by Vince ($188; vince.com); 510 trousers by Levi’s ($58; levi.com); textured knit hat by John Varvatos ($168; johnvarvatos.com); The 51-30 watch by Nixon ($450; nixonnow.com).