Stroll through the gorgeous Wolffer Estate winery and vineyard while tasting their incredible selection of wines. They even offer vineyard yoga, and who wouldn’t want to do that?

When: Sunday-Thursday 11am-6pm, Friday-Saturday 11am-8pm

Where: 139 Sagg Road, Sagaponack, NY 11962

For more information on Wolffer Estate.

This unique fest takes place at an airport and is slated to feature some of the biggest names in EDM, including Kygo, Disclosure, Claptone, and so many more! 

When: Saturday June 25th at 3pm

Where: Sheldon Way, Westhampton Beach, NY 11978

For more information on the Palm Tree Music Festival.

Halsey’s farm stand is open annually from June-November, and offers everything from plants to fresh produce to baked goods to fresh cut flowers. Buy yourself a bouquet and enjoy your main character moment. 

When: 9am-5pm daily, June-November

Where: 513 Deerfield Road, Water Mill, NY 11976

For more information on Halsey Farm.

Enjoy the chill vibes and amazing food and drinks at Gurney’s outdoor lounge, The Firepit. There’s no better place to take in the views during the day, or the upbeat energy at night. 

When: Monday-Thursday 3pm-11pm, Friday 3pm-12am, Saturday 11am-12am, Sunday 11am-11pm

Where: 290 Old Montauk Hwy Montauk, NY 11954

For more information on Gurney’s Resort.

The Surf Lodge may be known for its relaxed vibe, but they pull surprisingly big names for their annual summer concert series. Past performers have included John Legend, 50 Cent, St. Vincent, and Jimmy Buffet! 

When: Schedule varies

Where: 183 Edgemere St, Montauk, NY 11954

For more information on The Surf Lodge.

Moby’s is celebrating their 10th season this summer, and they’re bigger and better than ever. Grab drinks on their gorgeous lawn and indulge in some of the best Italian food in the Hamptons.

Where: 341 Pantigo Road, East Hampton, NY 11937 

For more information on Moby’s.

It’s hard to imagine that this prim and proper restaurant sitting along a marina can get rowdy, but when their infamous weekend DJ comes out, all bets are off! 

When: Wednesday-Thursday 12pm-3:30-9pm, Friday-Saturday 12pm-11pm, Sunday 12pm-8pm

Where: 1 Long Wharf Sag Harbor, NY 11963

For more information on Le Bilboquet.

Treat yourself to brunch at one of Southampton’s most famous restaurants! The sophisticated atmosphere, live music, and world-class service all make for one of the most bougie experiences you can have on a Sunday morning. 

When: Monday-Friday 10am-10pm, Saturday 9am-11pm, Sunday 9am-10pm

Where: 75 Main St, Southampton, NY 11968

For more information on 75 Main.

This little roadside gem is famous for their clams, so why not stop by and try a legendary coastal meal at a Montauk landmark? 

When: Everyday, 11:30am-sundown

Where: 2025 Montauk Highway, Amagansett, NY 11930

For more information on Clam Bar.

What better place to ~socialize~ than the Southampton Social Club? Not many places offer the same quality of food, drinks, or atmosphere as this hotspot, and almost nowhere stays open as late on the weekends.

When: Wednesday-Thursday 5pm-10pm, Friday-Saturday 5pm-4am, Sunday 5pm-10pm

Where: 256 Elm Street, Southampton, NY 11968

For more information on Southampton Social Club.

There are plenty of places to catch a live show, but none quite like the storied Stephen Talkhouse! This venue draws local acts and international performers alike, all in a uniquely intimate setting. 

When: Schedule varies

Where: 161 Main St. Amagansett, NY 11930

For more information on Stephen Talkhouse.

There is nowhere in the Hamptons more zen than this beautifully-appointed Japanese-inspired spa. Book a massage, facial, treatment or wellness ritual and leave feeling like your best self. 

When: Daily 10am-6pm

Where: 337 Montauk Hwy, Water Mill, NY 11976

For more information on Shou Sugi Ban.

Art enthusiasts and history buffs alike will appreciate a chill afternoon at the Pollock-Krasner House museum. Wander the grounds and uncover exhibitions new and old! 

When: By reservation only; Thursday-Sunday 12pm-5pm

Where: 830 Springs-Fireplace Rd East Hampton, NY 11937-1512

For more information on the Pollock-Krasner House.

The quaint village of Southampton has killer lunch spots and even better shopping. Take the afternoon off and enjoy milling around all of the cute boutiques. Stop by One Kings Lane to marvel at a pelortha of luxury home goods, including stylish pillows, bedding, art, and vintage pieces. 

Where: Southampton, New York

For more information on Southampton.