At 118 miles long, this sliver of New York lives up to its name. And there’s no shortage of things to do, either: A flight into Long Island MacArthur Airport places you just minutes from historic estates, world-class wineries, and some of the best beaches on the East Coast. Ready to go? First, tell us more about you.

Sure, the Big Apple is one of the world’s premier shopping destinations. But a short drive east of SoHo and Fifth Avenue, Long Island’s pedestrian-friendly main streets and shopping villages are studded with high-end boutiques, laid-back bargain bins, and everything in between. For those with deeper pockets, Amagansett Square, the Hamptons’ handsome retail-therapy hub, is fringed by friendly shops hawking vintage vinyl, fine home furnishings, surfboards, shoes, and more. Operating on a budget? Port Jefferson and the town of Huntington offer some thriftier alternatives. 

Tate’s Bake Shop:

Swing by Southampton for a brownie, blondie, or award-winning chocolate chip cookie. We bet you can’t eat just one.

Krisch’s:

Not much has changed at this 96-year-old diner and ice cream parlor since it moved to Massapequa in 1955. Think retro soda fountain and 10-stool counter.

Hampton Coffee Company:

This family-run roaster has four locations on the island, plus a mobile espresso unit that roams the Hamptons.

Cold Springs Harbor Antiques:

This multi-dealer showroom near Huntington is a gold mine of fine jewelry, period pieces, and imported accents.

Americana Manhasset:

The most sophisticated retailers this side of NYC—Gucci, Prada, Louis Vuitton—set up shop at this open-air center on the North Shore. 

Tanger Outlets:

Bargain hunters, take aim at this chain’s two locations (in Riverhead and Deer Park) for discounted designer threads.

In East End, former potato farms and once sleepy seaside villages have given way to more than three dozen wineries, making this side of L.I. a bona fide oenophile destination. Choose from a variety of tour companies or designate a driver and explore the region at your own pace. Our favorite spots: Shinn Estate Vineyards, because of its rustic tasting room and winery set in a restored barn; Lieb Cellars, for its inviting patio; and Bedell Cellars, where 30-year-old vines yield lauded reds, like its flagship Musée.   

Noah’s:

The menu changes daily to reflect local bounty, but you can’t go wrong with the seafood tower: clams, oysters, lobster, and shrimp.

Inlet Seafood Restaurant:

This Montauk mainstay is owned by six commercial fishermen who unload their daily haul just feet from your fork.

Lewin Farms:

The island’s first pick-your-own produce farm invites visitors to raid its orchards and berry fields. Peach season runs mid-July through mid-September.

Great South Bay Brewery:

Hop inside the 4,000-square-foot tasting room Wednesday through Sunday to sample a flight and then fill a growler for home.

LiV Long Island Spirits:

This farm-to-bottle operation is the first distillery on the island since the 1800s. 

Destination Agriculture:

Connect with local farmers on an educational—and tasty—greens and berries tour. 

Teddy Roosevelt would approve this message. As a key figure in our nation’s early conservation efforts, the 26th president would no doubt endorse last summer’s completion of a $10 million restoration of his “summer White House,” Sagamore Hill. Take a guided tour of the mansion, stand on the porch where T.R. gave speeches, and glimpse his famous Rough Rider hat, hanging on the antler of a mounted elk head in the North Room. Presidential politics wearing you out? Elect instead to visit Walt Whitman’s birthplace in Huntington Station or Jackson Pollock’s house in East Hampton.

Jedediah Hawkins Inn:

This romantic B&B, built as a sea captain’s home in 1863, is flanked by farms that supply ingredients to its two on-site restaurants.

Oheka Castle:

Live like royalty (at least temporarily) in one of 32 lavish rooms at this over-the-top Gilded Age mansion along the Gold Coast.

Montauk Manor:

This majestic, 1920s-era hotel boasts 140 units, many with sweeping views of the Atlantic Ocean, Gardiners Bay, and Block Island Sound. 

Cradle of Aviation Museum:

Climb inside cockpits or stand back and marvel at more than 75 aircraft at this tribute to Long Island’s aerospace heritage.

Long Island Museum:

This nine-acre complex in Stony Brook owns one of the nation’s finest collections of horse-drawn vehicles. 

Old Westbury Gardens:

Stroll through the Gatsby-esque former home of financier John S. Phipps, through October 31.

Set in Old Bethpage Village Restoration, surrounded by woods, farmlands, and fields, this year’s Tough Mudder (July 23) will be anything but a walk in the park. Among the teams planning to plunge into icy trenches, scale 16-foot walls, and trudge through waist-deep mud pits: a team of doctors, patients, and staff from North Shore Hematology Oncology Associates. NSHOA is raising money for its foundation, Advocates for HOPE, which helps cancer patients with non-medical expenses. “Last year, our goal was simple: Start and finish as a team,” says Dr. Jeff Vacirca, CEO and clinical oncologist. “We all finished—dirty, bruised, and banged up, but unbelievably happy.”

Paddling:

Rent a boat or stand-up paddleboard from Long Island Canoe Kayak Rentals, part of Treasure Cove Resort Marina, and explore the picturesque Peconic River. 

Floating:

Snag an H2GO pass at Splish Splash and skip the lines for the quarter-mile lazy river, speed slides, New York’s first hydromagnetic water coaster, and more.

Surfing:

Managed by pro big-wave surfing brothers Cliff and Will Skudin, Skudin Surf offers camps, group classes, and private lessons for adults and children. 

Montauk Point State Park:

Ascend the 132-step lighthouse and then watch the tides of the Atlantic Ocean and Block Island Sound converge.

The Adventure Park:

Located in Wheatley Heights, the park’s aerial ropes courses are suitable for climbers of all levels, ages 7 and up.

Bethpage State Park:

Take a swing at the Black Course, which hosts the PGA’s The Barclays tournament in August.