10 Must-Visit Reasons to Plan a Long Island Getaway This Season
Long Island is famous for its celebrity-filled summer beaches, but savvy travelers know it's a year-round paradise. Discover award-winning wineries, historic landmarks spanning centuries, and breathtaking views—all blissfully uncrowded during the off-season.
Enjoy more space, lower rates, and easy access to top attractions. Whether driving from New York City, riding the Long Island Railroad from Penn Station, ferrying from Connecticut, or flying into Long Island MacArthur, LaGuardia, or JFK airports, use this travel info hub to plan your trip. Here are 10 standout destinations:
Huntington
Along the North Shore, the Gold Coast boasts Gatsby-era mansions. Tour them by car or stay at OHEKA Castle, once financier Otto Hermann Kahn's estate—featured in Citizen Kane and Taylor Swift's Blank Space video.
As a Gilded Age hub, Huntington excels in arts and culture. Visit the Heckscher Museum of Art for exhibits like Rivera and Beyond: Latin American Art from the Joan and Milton Bagley Collection, showcasing masters such as Fernando Botero, Wifredo Lam, and Elena Climent.
For live performances, catch shows at the Paramount featuring acts from Kansas to Ken Jeong (Crazy Rich Asians star).
Stony Brook
This arts haven offers the Jazz Loft with jazz legends' instruments, diaries, and scores, plus the Long Island Museum of American Art, History and Carriages—a Smithsonian affiliate displaying over 100 horse-drawn carriages from the 1700s.
Nearby, explore The St. James General Store (est. 1857) for molasses candy, pottery, and holiday Santa visits. Along Route 25A, follow Washington's Spy Trail signs tied to George Washington's spies during the British occupation (see AMC's Turn). Stay at Three Village Inn, with cottages named after those spies.
Port Jefferson
Enjoy stunning harbor views at Wave Seafood & Steak in Danford's Hotel and Marina—famed for epic Sunday brunch and fish & chips. Winter fun includes ice skating (November-March) and the annual Dickens Festival (Dec. 1-2) with A Christmas Carol characters.
Mattituck
In the North Fork's farm and vineyard country, Mattituck boasts 30+ wineries. Families love Harbes Family Farm for animal feeding, hedge mazes, hayrides, and sustainable wines at the barn.
Dine at Love Lane Kitchen for seasonal fare like pancakes or pastrami hash. Stay at Shinn Estate Vineyards Bed & Breakfast, a restored farmhouse with organic breakfasts and complimentary tastings.
Greenport
Beyond wine, try craft brews at Greenport Harbor Brewing Company's tasting room—seasonal like Leaf Pile Ale or Anti-Freeze Ale, often with live music.
Savor destination dining at Noah’s by chef Noah Schwartz, praised by New York Times and James Beard Foundation. Try Crescent Farm Duck BBQ. Stay nearby at Ruby’s Cove or Harbor Front Inn.
Sag Harbor
This South Fork whaling village inspired authors like James Fenimore Cooper, John Steinbeck, and Betty Friedan. Visit Bay Street Theater (next: The Great Gatsby) and Canio's Books for events. Whaling fans: Sag Harbor Whaling & Historical Museum. Stay at historic The American Hotel (1846).
Montauk
Stay at Hero Beach Club (fire pits, s'mores) or Gurney's Inn & Spa. Brew at Montauk Brewing Company; dine on small plates at Swallow East. Climb the Montauk Point Lighthouse (1792, George Washington-commissioned)—check here for hours.
East Hampton
In the Hamptons, enjoy dining (East Hampton Grill's Heavenly Biscuits), shopping (Kirna Zabête, What Comes Around Goes Around), and people-watching. History at Home Sweet Home Museum; seafood at Wine Spectator-awarded 1770 House.
Sayville
Experience the South Shore's charm at original Butera's for family-style Italian—chicken meatballs, grilled pizza. Visit Long Island Maritime Museum for shipwreck artifacts; shop Island Strong for nautical gear.
Fire Island
Car-free and pristine, stay at The Palms Hotel in Ocean Beach for ocean views. Explore Sunken Forest boardwalk and 160-year-old Fire Island Lighthouse. Catch the Reenactment of the Flying Santa on Dec. 8.
