Long Island Trip Planning & Vacation Ideas

With so many activities on Long Island, there’s a lot to see and do.

We tried to make it a little easier for you. If you’re looking for things to do that suit your interest, take a look at some of our ideas below.

Maybe you’re traveling with your family, or with a partner. Maybe you’re an adventurer. Maybe you prefer history. We’ve created some itineraries that might interest you. Get started planning your Long Island Vacation.

You can also request a free Travel Guide or take a look at our Interactive Map page to start planning your trip.

A Long Island Adventure

Long Island Adventure Itinerary Day 1. Tearing Up the Beach If you’ve never tried ‘fat-biking’ on the beach prepare yourself for a unique adventure, because those big wheels will take you wherever you want to go. Rent a bike and...

A Trip With The Kids

Day 1. Fun in the Sun - A day of ocean adventure is waiting (as if a visit to the beach wasn’t exciting enough). Set up your spot on the sand early at Long Beach and reserve an exciting surfing...

Experience Long Island

Day 1. Old Westbury Gardens, Old Westbury, NY. Step into the Gatsby-era in a stately furnished Charles II style mansion, home of the Phipps family. Tour the magnificent home and explore the 160 acres of beautifully maintained gardens, sweeping lawns,...

Famous Beaches of Long Island

Need help trying to find the perfect Long Island beach? You can choose from below, or plan a trip to see them all only on Long Island, New York City's Beachfront Backyard. Day 1. Closest to the City - If...

Lighthouses, Beaches and Wine

Day 1. Fire Island Lighthouse, Fire Island, NY is accessible via a ¼ mile walk along a boardwalk on the west side of Robert Moses State Park. Park at Field 5. At 167-feet, it is Long Island’s tallest lighthouse tower....

Long Island Gilded Coast

Day 1. Explore Long Island’s Castles - Just a short ride from New York City on Long Island’s north shore is a place of uninhibited wealth and opulence immortalized in F. Scott Fitzgerald’s book, The Great Gatsby. Many of the...

Long Island Wine Country

Day 1. The North Fork Begin your trip by spending a slow day in Riverhead, where you can explore the downtown and main street or shop around for deals at the Tanger Outlets. Take in the spectacles of the Long...

Poets, Presidents and Artists

Day 1. Walt Whitman Birthplace - A friend of his once claimed "You cannot really understand America without Walt Whitman," and it is clear why with a collection of works that so deeply reflect American culture. Visit the birthplace of...

Roadside Attractions

Take a tour of some of Long Island’s quirkiest roadside attractions. Many have unusual stories and legends associated with them. Day 1. Big Chief Lewis, Massapequa, NY. Near Rte. 107, the Chief has a totem pole, buffalo, and a pink...

The Angler Experience

Day 1. Jones Beach and Long Beach - Great for fish or general beach entertainment, Jones Beach features a long boardwalk, performance venues, vendors, a fishing station and more. Field 10 fishing station offers a pier to stand on, but...

The George Washington Spy Trail

Tour the George Washington Spy Trail Day 1. Execution Rocks Take a boat excursion to Execution Rocks lighthouse just off Sand’s Point to learn how British colonial authorities are said to have executed ‘Rebels’ by chaining them to the...

Up in the Air

Day 1. A Day at the Museums – Start out with a refresher course on all that Long Island is known for when it comes to aeronautics with some help from the Cradle of Aviation and the American Airpower Museum....

Explore Long Island Ocean Beaches