Top Summer Spots on the East End of Long Island

I am currently planning a few seasonal getaways and I thought I'd share some of my favorite summer spots from where I grew up--Long Island.

Long Island is the best place to be in the summertime. It has tons of beaches, bars, restaurants, wineries, breweries, sports arenas, shopping and more. I live in the Philadelphia area now but I always plan to visit home as much as I can during the summer. It feels like a vacation every day. A few tips: plan your trip in advance, get to where you're going early (traffic is crazy out east, with a lot of people and few roads), be respectful of the locals and enjoy yourself!

Here are my top spots from "way out east," where I grew up:

The Beach

It doesn't matter where you go--the Sound, the ocean, even the bay or a lake--Long Island has tons of water. It has more than 400 miles of coast, and the beach is never more than 15 miles from you at any point. I truly miss it, as the closest beach to Philly is the Jersey Shore (still great, but far!). I've swam in the Atlantic, the Long Island Sound, even the Peconic Bay and Lake Panamoka, and it's always a good time. I actually prefer the Sound over the ocean, as it's closer to my family home, we belong to a private beach club, and it's quieter.


Claudio's is a summer tradition for my family. My parents brought us out to Greenport as kids for the food and to walk around, and as adults we go out for some drinks and fun. I love to get a bucket and enjoy the sunset from the dock on the bay. The live music is great and you always end up seeing someone you know.


Oaklands is a fun restaurant and bar on the water on Dune Road in Hampton Bays. I like to go out and watch bands play there--especially my uncle's band, Heart and Soul (shameless plug). This south shore spot has great food and an outdoor bar.

Phil's Waterfront

Seeing a theme here? I love restaurants on the water. I grew up in Wading River, which has the original Phil's--your basic sports bar. I always like going to Phil's, but I love the new setting on the creek in Riverhead.

The Wineries (and Other Beverages)

I can't limit this to just one--there are more than 60 wineries on Long Island, and 1.3 million people visit them every year. The most western vineyard is Baiting Hollow Vineyard, which is fun but tends to get very crowded. They have a large tent and are open in the winter. I prefer some wineries that are a bit quieter--I like Roanoke Vineyards and Sherwood House Vineyards. But honestly, they are all great. Try a limo wine tour and check out a few at a time. Wine not your thing? There is Long Island Vodka on Sound Avenue next to Baiting Hollow Vineyards, and also the Riverhead Ciderhouse and Long Ireland Brewing Company.

Walkable Towns

There is a lot of great shopping, eating and things to do in many towns on the island. I enjoy walking around Port Jefferson, Sag Harbor, Patchogue and Greenport--window shopping and checking out new restaurants.

I could list many, many more places, but these are my favorites. Here are some restaurant honorable mentions:
  • Cooperidge Inn in Baiting Hollow 
  • Pera Belle in Riverhead
  • The Pie in Port Jefferson
  • Porto Bello in Greenport
  • Pure North Fork in Wading River
  • Seaside Grill (at the Hyatt) in Riverhead
  • Toast in Port Jefferson



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