Winter Surfing With Caleb Thill

Can’t start my day—especially a surf day—without a good cup of coffee!
 

Gurney’s in the winter is truly a magical snow globe.
 

Grabbing breakfast at the iconic John’s Pancake House before heading out to surf.

Everyone thinks winter surfing is freezing. But getting into your wetsuit is actually the coldest part—once you’re suited up, you really don’t feel the chill, even when you’re in the water!

Ditch Plains is the iconic surfing spot in Montauk, but it’s hard to access without a parking pass. On top of that, Ditch Plains is a left point break, and I surf regularly, so I prefer right breaking waves. My trick is to park at Shadmoor State Park and hike to the beach (it’s about 10 minutes on foot) where a lot of the waves break right—just be careful, there’s a steep cliff you have to climb down to get to the right spot.

Truly a spectacular view.

The path you’ll need to climb down in order to get to the water—it’s not as hard as it looks!

Waxing my board and watching the waves before I jump in for a golden hour surf session.

Montauk has always been a special place to me; my great aunt used to live here, and I remember driving out as a kid to visit with family. A lot has changed since childhood, but the one thing that hasn’t changed is the thing I love most: the ocean. That’s what I crave—and it’s what keeps me coming back.

[As reported to Gurney's Montauk by lifestyle, fashion, and travel influencer Caleb Thill]