There is nothing quite like a Long Island summer. All year long locals and those who have been lucky enough to visit, dream of the season filled with spectacular boat days, the best lobster rolls in the world, outdoor concerts at the iconic Jones Beach, lawn parties where the rose is flowing and so much more.
From wine tasting among a sea of flower fields, to diving with sharks off the coast of Montauk, there is no shortage of epic outdoor experiences across the region. That’s why we gathered some of the most bucket-list worthy adventures for living your best Long Island Life this summer. While some include iconic destinations and events proudly home to our region, the list offers many incredible off-beat experiences and hidden gems that will help make summer 2022 the best one yet.
You’ve done paddle boarding and kayaking so kick it up a notch this year and try wakeboarding! And you don’t have to head to Long Island’s crowded East End for an ‘Over the Top’ experience. Over-The-Top Watersports charter and rental company is in the heart of the historic, harbor front village of Northport, which still bears the trolley tracks laid in the early 1900’s as well as the vintage sweet shop operating since 1929. The watersports company offers Wakeboarding, Wakesurfing, and Waterskiing, lessons for all ages as well as tubing – just for fun! Not ready to hit the waves? Take a cruise during golden hour and capture unrivaled views (and photos) of the Northport’s harborside hills lined with sailboats and stunning Victorian style homes before pulling up to a local dockside restaurant for dinner by boat.
Long Island’s historic Gold Coast is home to stunning grand estates set against pristine gardens and shimmering coastlines. Tour the mansions of the Roaring Twenties where industry tycoons (including the Vanderbilts and Guggenheims) reigned supreme and served as the inspiration behind The Great Gatsby. Stay overnight at the luxurious OHEKA Castle, often serving as a set for major Hollywood productions. A few must-see mansions for the ultimate gilded age experience Old Westbury Gardens (Westbury), Sands Point Preserve (Sands Point), Coe Hall (Oyster Bay), Glen Cove Mansion (Glen Cove), Chelsea Mansion (Muttontown), and Marshall Field Estate (Lloyd Harbor).
Long Island has long been a golfer’s paradise for those “in the know.” As the host destination of 23 major golf championships, the region’s relationship with the professional sport dates back to the late 1800s. Most recently, Bethpage Black Course hosted The 2019 PGA Championship, the 2012 and 2016 Barclays PGA Tour events, and is set to be the site of the 2025 Ryder Cup—the biggest international golf event in the world. And the best part is, it’s a municipal course so it’s open to the public and you can even swing on the same course as some of THE best pro golfers to ever have lived.
WildPlay Element Park at the iconic Jones Beach will put your endurance to the test with its many rope courses, 700-ft. long zipline, and 40-ft. bungee jump while overlooking the most visited beach in the state. With three levels of obstacles to choose from, the park is the perfect place for kids and adults alike. Afterwards, hit the Jones Beach Boardwalk for even more family-friendly activities, food, and beach access.
The combination of restaurants and workboats, open-air bars and fish markets, live music and foghorns on the Nautical Mile provides a unique blend of nautical charm and street fair revelry that you won’t find anywhere else. Seafood lovers can enjoy a slate of open-air eateries right outside or on one of the busiest docks on the South Shore offering mussels, clams, blue crabs, and lobsters. A few staples include Hudson’s on the Mile, Jeremy’s Ale House, Rachel’s Waterside Grill, and Elliot’s on the Mile. On summer nights, hundreds of locals flock to the strip flanked by water where antique lighting shines over the bustling sidewalks and where party boats line up along Woodcleft Canal. The Nautical Mile is not just a must-see destination for partiers and seafood lovers. It is one of Long Island’s best family friendly attractions featuring mini golf, a four-acre waterfront park, dinner cruises, fishing charters, and more.
Rocking out to a legendary band under the sky on a hot summer night at the oceanfront Northwell Health at Jones Beach amphitheater has been a perennial favorite of Long Islanders for decades. Jimmy Buffett has been among the most frequent acts at Jones Beach, performing his annual summer show and tailgate party here for many years. Highlights of the A-listers performing at the iconic Jones Beach venue this summer include the Backstreet Boys, Third Eye Blind, Chris Rock + Kevin Hart, Train + Jewel & Blues Traveler, Lynyrd Skynyrd, Tim McGraw, Dave Matthews Band, Steely Dan, The (formerly Dixie) Chicks, Josh Groban, Rod Stewart & Cheap Trick, Chicago and so many more!
Rated by Wine Enthusiast as one of the ‘Top 10 Wine Regions’ in the world, Long Island Wine Country is home to over 60 vineyards and world-class tasting rooms. From rich Cab Francs to versatile roses and legendary bubbly, regional-inspired brews, and top-shelf liquor, Long Island has grown award-winning, high-quality ingredients for wines and spirits in unmatched settings where winding farmlands and waterfront vineyards serve as picturesque backdrops.


