Favorite Long Island Summer Activities

Long Island Summer Activities

The Summer is pretty much halfway over, but there is still some solid time left to venture out and enjoy everything Long Island has to offer. With that said, I want to share some of my favorite Long Island summer activities I enjoyed thus far. In no particular order we have the following super fun activities and my pro tips for how to maximize each experience.

Christeen Oyster Sloop in Oyster Bay

The Christeen was built on Long Island in 1883 but offers such an amazing experience that truly holds up to this day. The crew provided by the Waterfront Center in Oyster Bay is so friendly and knowledgeable that you really develop a better understanding of historic Oyster Bay and the adjoining harbors. This was probably one of my favorite Long Island Summer activities and I plan on doing it again. Tours can be booked through the Waterfront Center of Oyster Bay and if you have a large enough party you can charter the entire board for under $80 a person – click here for more information: https://www.sailchristeen.org/.

Fun under sail on the Christeen Sloop

Boomer Pro Tip: Pack a cooler of cold beverages like some crisp pilsners or a nice rose like McCall Wine’s Marjorie’s Rose. Also, aim for the sunset cruise as the light really reflects nicely off the water and lights up all the colorful sailboats in the harbor, which you will learn all about.

Kayaking with the Waterfront Center In Oyster Bay:

Also located at Theodore Roosevelt Park in Oyster Bay is their kayak rentals. For a very reasonable price you can take out a single or double kayak or stand-up paddle board for as long as you want and explore the west side of Oyster Bay. This is such a wonderful way to stay cool on a hot summer day and you can even bring your four legged first mates! Chewie always has a great time but doesn’t always stay in the boat. To book a kayak or SUP click here: https://www.thewaterfrontcenter.org/ 

long island summer activities include kayaking
Tandem kayaking with our Chief Lazy Officer, Chewie

Boomer Pro Tip: The new fleet of kayaks offers a nice dry compartment in floor of the boat so feel free to bring you mobile phone if you want to take photos, you’ll be able to keep it dry. However, you might want to pick-up a dry bag to keep other things dry if you intend to take a swim off the kayak. Doing so will surely get water all over the place.

Surfing & Beaching at Ponquogue Beach

I tend to surf at Tobay Beach because I like how uncrowded the lineup is but sometimes you just can’t find rideable waves middle island so when that happens, I’ve started driving out to Hampton Bays and been checking out the Southampton Town beach at Ponquogue. If you get there before 8am you don’t have to pay for parking, but you can still purchase a day pass to one of the few beaches in Southampton that allows non-residents. The surf is great and they have nice concessions and bathroom facilities. It’s a fun way to make a trip out East without having to deal with the normal craziness of the South Fork. Click here for more info: https://www.southamptontownny.gov/

long island summer activities ponquogue beach
Great accessible beach in the Town of Southampton

Boomer Pro Tip: Finding out the hard way, the restrooms are not open before 8am so if you are doing a dawn patrol and the coffee kicks in make sure you have a roll of TP in the car because they at least have a couple of port-o-johns. Also, on the ride back there is a great roadside breakfast place called The Hamlet and the bacon egg and cheese really hits the spot after a couple hours of surfing. Check them out here: http://www.thehamlet.space/index.html

Wineries on the North Fork of Long Island

For the longest time my desire to always find surf kept me focused on the South Fork. But finally, about six years ago we decided to give the North Fork a chance and boy am I kicking myself for not trying it sooner. There are so many good wineries out east past Riverhead and right up till Orient Point, and making it a day trip from Nassau County is very doable. My favorite winery is McCall Wines but depending on your preference, from Rose and Chardonnay to Cab Franc and Pinot Noir, there is a winery for you. Also, because of the maturity of the vineyards (the North Fork Wine Region turns 50 years old this year) there are some really great wines to enjoy. So support locally grown and enjoy this classic Long Island Summer Activity!

McCall Winery
Chardonnay and Pinot Noir at McCall Wines in Cutchogue

Boomer Pro Tip: If you like a secluded & laid-back, party bus free vibe check out McCall Wines at https://www.mccallwines.com/. I love their Ben’s Blend and the Unoaked Chardonnay but make sure to get the cheese and charcuterie board, treat it as a lunch. Also, Kontakosta Winery not only has great white wines, but they have a beautiful waterfront access cliff overlooking the Long Island sound that really adds to the vibe and the day. https://www.kontokostawinery.com/

Little Creek Oysters in Greenport Harbor

Lastly and certainly not least, is my favorite summer hangout, Little Creek Oysters. Whether you like a dozen oysters ready to eat or you like shucking them yourself as you enjoy a cold local Greenport Harbor Brewing Co. beer, nothing feels more ‘Long Island’ in the summer than enjoying some of the world’s best oysters from the Peconic Bay. They usually have a nice variety of oysters, and the rustic atmosphere is ideal for people seeking good summer times. Check out their website here: https://littlecreekoysters.com/

Little Creek Oysters in Greenport Harbor
Shucking it up at Little Creek Oysters

Boomer Pro Tip: They give you a discount on the oysters if you shuck them yourself so give it a shot. They provide the heavy glove and a great shucking knife. It’s easy to pop them open. Simply insert the point into the back end of the oyster “the joint” wiggle the tip in and turn the blade like a key and that should be it. If you get the hang of it you’ll be an official oyster shucker and you’re summer party guest status will skyrocket when you say something like, “I’ll bring some oysters”.

Peconic Gold Oysters of Long Island
Peconic Gold Oysters are one of my favorite around

Ari’s Bonus Pro Tip: Since you read this much you are probably an oyster fan. If you didn’t have enough oysters at Little Creek, you can pick up some of the freshest and tastiest oysters on the side of a few country roads as you drive back home through the North Fork. Peconic Gold Oysters stocks a ‘honor system’ cooler where you can pick up a bag or a dozen oysters, and knife if you need one. Simply have a cooler stocked with ice with you and Venmo Captain Matty his $25 and be on your way with some of my favorite oysters. They should stay in your fridge for seven days or so, but I’d personally get after them in five days.

Of course, there is so much more to do on Long Island, but I just had to serve up some of my favorites. Happy summering friends and maybe I’ll come up with some ideas for fall. Click the following link if you have any questions for me. 

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