The Perfect Hamptons Memorial Day Weekend Plan

If you’re reading this, print it out. It’s easy to screw up Memorial Day Weekend and that’s the last thing you want to do. It’s been two years since we’ve been able to truly enjoy ourselves in the Hamptons. Do not hesitate. Make reservations, and follow this guide.

Morning –
7:00am – Wake up in the morning and immediately head to the beach for a morning run. Just jog from beach to beach, it will be about a mile and a half. When finished, jump in the ocean, be sure to bring a towel.

8:30am – Rally everyone in the house to wake up and get everyone out the door for breakfast and then the beach. If you have kids under 10 years old, go to a bay beach, if they are over 10 go to the ocean. If you have no kids, go to the ocean. Make sure your car is packed with towels, a cooler with waters, ice, drinks, bagged popcorn and granola. Pack sunblock, magazines, a large blanket, beach chairs for each person going and beach umbrellas for each person going. If you do not have these items purchase them at the nearest CVS/pharmacy/hardware store in whatever town you’re in.

9:00am – Stop for breakfast at any of the following places: Goldberg’s Bagels, Jack’s Stir Brew, Sagtown coffee, Springs General Store, Starbucks, Carissa’s Bakery, Pierre’s, Provisions, Joni’s (Montauk).

9:30am – Spend the day at the beach until 12:30pm. If you are insane and not going to do the beach or want to switch things up, other fun adventures are hiking Camp Hero to the Lighthouse in Montauk. You could also hit a spa during this time; good spots for this are Gurney’s, Naturopathica or A Studio Spa. This time can also be set aside for doing a Viking fishing trip in Montauk, hitting golf balls at Poxabogue in Sagaponack or the driving range in Southampton, or you could do a SUP adventure with Paddle Diva. The key thing is to make the decision on where you’re going NOW.

1:00pm – It’s lunch time. Make this reservation after you read this article for any of these restaurants. Reservations are key in the Hamptons. Great lunch spots that I like are Union Burger, Lobster Roll, Bobby Van’s, American Hotel, Sen, Wolffer Kitchen, Le Bilboquet, Cittanuova, Carissa’s Bakery, Hampton Chutney, Sant Ambroeus, 75 Main, Organic Krush and Navy Beach (Montauk).

3:00pm – Head back home, shower and get resettled but start getting dressed immediately. You’re about to rally again.

5:00pm – You’re out the door and you’re heading to the Wolffer Vineyards Wine Stand. Call in advance, it gets very busy there. For a backup plan, go to the Channing Daughters Vineyard if it’s too crazy and if you’re not in the area, do a drink at Duryea’s in Montauk or at the Gastro Pub in Southampton for a little outdoor cocktail. Drink light and don’t have dinner here, that’s for two hours from now, and remember, always have a designated driver, Uber, or hire a driver.

7:30pm or 8:30pm or 9:30pm – Head out to a restaurant. It’s Memorial Day, so one of the nice things to do is to dine on the water. Some great sunset restaurants are Le Bilboquet, Beacon, Bostwick’s, Surf Lodge, Gurney’s, Duryea’s, Crow’s Nest, Harvest on Fort Pond, Navy Beach; if you’re in Hampton Bays a great option is Cowfish. ALSO, don’t forget, the Sag Harbor Movie Theater is going to have new Top Gun playing this weekend, so if you’re not into dinner for the evening, just grab a slice or a quick meal at home and go there to watch this movie. After all, it’s Top Gun.

11:00pm – You’re either in bed or you’re rallying again to go out at night. Do not mess around, get a designated driver, hire a driver for the evening to drive your car by asking anyone in your network if they know anyone interested, or rely on taxis/uber. Whatever you do, do not drink and drive. It will ruin your entire vacation. For nightlife, great spots are Stephen Talkhouse, Surf Lodge, Sole East, Clubhouse, Southampton Social Club, Blu Mar, Rumba (Hampton Bays), Beach Bar (Hampton Bays).