Your End-of-Summer Hamptons Bucket List

Five experiences to savor before the season fades

Somehow, it’s already August, and summer in the Hamptons is doing that thing it always does—flying by. Before you trade beach bags for blazers, here’s a short and sweet bucket list of local adventures to squeeze in while the days are still long and the water’s still warm.

1. Tuesday Sail on the Luna

Every Tuesday in August, Sail Hamptons takes the beautiful blue-hulled Luna out for a sunset cruise—and it’s just as dreamy as it sounds. Step aboard in Sag Harbor, watch the sails fill as the shoreline slips away, and let the sky melt into shades of pink and gold. It’s the kind of weeknight reset that makes you forget what day it is, in the best way.

2. Take an Art Class at the Art Barge

Perched right on the Napeague Harbor, The Art Barge is one of those quirky, beloved Hamptons institutions that feels unchanged by time. Their late-summer workshops are pure creative therapy—whether you’re painting, drawing, or collaging with the windows thrown open to the sea breeze.

3. Dinner & S’mores at The Pridwin

The Pridwin on Shelter Island is the definition of nostalgic summer charm. Head over for a family dinner on the deck—think fresh fish, classic cocktails, and views of the water—then wander down to their firepit for s’mores under the stars. The ferry ride there and back makes it feel like its own little getaway.

4. Sip Something Unexpected at Channing Daughters

Yes, everyone knows Wölffer, but Channing Daughters is the Hamptons’ under-the-radar winery gem. Known for their creative blends and striking bottle art, it’s the perfect low-key tasting experience. Try their orange wines or rosatos while wandering the sculpture garden for a dose of both art and nature.

5. Beach Day at Ditch Plains

Ditch Plains is where surfers, locals, and in-the-know visitors all converge. Even if you’re not paddling out, it’s endlessly entertaining to watch the surfers from the sand. Pack light and plan to have lunch from the iconic Ditch Witch food truck—everything from breakfast burritos to fresh poke bowls.

The clock is ticking—September will be here before you know it, but that doesn’t mean summer has to slip away unnoticed. Check a few (or all!) of these off your list, and you’ll roll into fall with that sunkissed, saltwater-in-your-hair feeling still lingering.