The sommelier weekend itinerary crafted by Jesse of Sen restaurant in the Hamptons:

Montauk Moments

Mid-September every year I head out to Montauk for a retreat with a crew of sommeliers. It’s an annual surf-and-wine escape – a Sunday to Tuesday stretch of great bottles, even better seafood, and just the right amount of chaos.

Where We Stay: Montauk Beach House 🏨

We post up at the Montauk Beach House – beautiful rooms, great atmosphere, and the perfect home base. First night, it’s all about hanging out, opening up wild wines, and easing into Montauk mode.

Morning Move: Left Hand Coffee & Ditch Witch ☕🏄‍♂️

We start at Left Hand Coffee – a cool, unfussy spot with solid coffee. I usually go black, but when I want something more, a dirty chai latte (with a double espresso shot, obviously) does the trick.

From there, we head to Ditch Plains for a morning surf session. 

If we’re lucky, Ditch Witch food truck is parked nearby, dishing out beachside breakfast burritos and whatever else we feel like inhaling post-surf.

Dinner Moves: Where to Eat in Montauk 🍽️

For big groups, it’s got to be Harvest – large family-style plates, solid food, and a lively scene. 

Another solid pick: Navy Beach. Great cocktails, ocean views, and, if I’m being honest, I’m usually too deep into the night to remember exactly what I ordered – but I know it was great.

Across the water from Gosman’s, Inlet is another solid spot. The food is great, and the setting is hard to beat.

Inside Tip 📌

If you’re cooking, go straight to Gosman’s. Even though it’s a wholesaler, the retail counter is open all summer long. Just ask what was caught that day and build your meal from there.

About Jesse

This card is by Jesse Matsuoka, a Hamptons resident of over 25 years. Jesse is a sake sommelier, Tip Top Hospitality partner, and co-owner of Sen, a legendary Japanese restaurant in Sag Harbor. Jesse was born in Manhattan, grew up in Tokyo, Hawaii, and Sag Harbor, and is now married to a third-generation Montauker.

Lead-in Image

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