Long Island might just be one of New York’s best-kept secrets when it comes to epic road trips.
You’ve got everything here—beaches that’ll make you feel like you’re on vacation, adorable towns with killer seafood, and even spots packed with history and old-school charm.

Whether you’re in the mood for outdoor adventures, lazy days by the water, or exploring places that feel straight out of a movie, Long Island has something for you.
This itinerary will take you to hidden gems and iconic landmarks, and trust me, you won’t want to miss a single stop!
1. Garden City

Garden City is a charming village located in Nassau County on Long Island, just about 20 miles from Manhattan.
It’s famous for its tree-lined streets, gorgeous historic homes, and the Roosevelt Field Mall, which happens to be one of the largest shopping malls in New York.
If you’re into history, check out the Cradle of Aviation Museum, where you can learn all about Long Island’s role in aviation and even see actual planes from World War II.
Fun fact: Garden City was founded in the 1800s by millionaire Alexander Turney Stewart as one of the country’s first planned communities, so walking around feels like stepping into another era!
2. Port Washington

Port Washington sits right on the North Shore of Long Island, offering stunning waterfront views and a chill, coastal vibe that’s totally different from Garden City’s more suburban feel.
It’s a great spot for boating, with marinas and docks lining the harbor, plus you can hop on a water taxi to explore the area from the water.
Head to Main Street for cozy cafes, boutique shops, and some seriously good seafood—Louie’s Prime Steak & Seafood is a local favorite and has been serving fresh clams and oysters for over 100 years!
(Please note Louie’s is closed for renovation until Spring 2025.)
For a little slice of Hollywood trivia, Port Washington is where F. Scott Fitzgerald got his inspiration for the fictional neighborhood East Egg in The Great Gatsby.
3. Sands Point Preserve

Just a short drive from Port Washington, Sands Point Preserve feels like stepping into a fairy tale with its sprawling estate and jaw-dropping mansions.
One of the highlights is Castle Gould, a massive medieval-style castle that was built in the early 1900s and looks straight out of a movie—it was originally meant to be a horse stable, if you can believe it!
The preserve itself is perfect for a laid-back day of exploring, with hiking trails, quiet beaches, and beautiful gardens where you can kick back and soak in the scenery.
It’s also a popular spot for outdoor events like yoga classes and summer concerts, so keep an eye on the schedule if you’re planning your trip.
4. Oyster Bay

Next up is Oyster Bay, a historic gem on Long Island’s North Shore that’s full of small-town charm and big-time history.
You absolutely can’t miss Sagamore Hill, the home of Theodore Roosevelt, where you can tour the rooms he lived in and walk the same trails he loved—seriously, it’s a great way to explore presidential history.
If you’re into the outdoors, stop by Theodore Roosevelt Memorial Park, which has picnic spots, a peaceful waterfront, and even a playground if you’re traveling with kids.
Make sure to grab some fresh seafood while you’re here—there are plenty of spots serving up oysters (of course!) and other local catches right by the bay.
5. Huntington

The next stop on our road trip is the lively town of Huntington with its walkable downtown packed with cool spots to eat, shop, and hang out.
If you’re into live music, the Paramount is an absolute must—it’s a legendary venue where big-name bands and comedians perform in an intimate setting.
History buffs will love stopping by the Walt Whitman Birthplace, where you can learn about the famous poet’s life and even see his original handwritten manuscripts.
And for some fresh air, Caumsett State Historic Park Preserve is just a short drive away, offering miles of trails through woodlands and along the waterfront—perfect for stretching your legs after a day of exploring.
6. Port Jefferson Harbor

Port Jefferson Harbor, located within the village of Port Jefferson, is the perfect spot to relax and soak in those waterfront views.
The harbor area is full of things to do—grab some homemade fudge at one of the cute candy shops, wander through the boutique stores, or just chill out on the docks and watch the ferries come and go.
If you’re hungry, hit up spots like Danfords or The Steam Room for seafood that’s as fresh as it gets—think lobster rolls, clam chowder, and all the good stuff.
You can even catch a ferry to Connecticut from here, but honestly, Port Jeff is so cozy and inviting, you might just want to stick around and enjoy the vibe.
7. Greenport

Greenport is a hidden gem located on Long Island’s North Fork, it’s filled with small-town charm that makes it feel totally one-of-a-kind.
This spot is known for its amazing wineries and tasting rooms—like Kontokosta Winery, where you can sip local wine while looking out over the Long Island Sound.
Downtown Greenport is packed with character, from the historic carousel in Mitchell Park to the waterfront restaurants serving up fresh seafood and craft cocktails.
For something a little different, check out the Railroad Museum of Long Island or rent bikes and cruise around town—it’s the kind of place where every corner feels like an adventure.
8. Orient Beach State Park

Just a short drive from Greenport, Orient Beach State Park is a peaceful escape at the very tip of the North Fork, where it’s all about nature and low-key vibes.
This spot is perfect for kayaking or paddleboarding through quiet coves, with amazing views of Gardiners Bay and the Long Island Sound.
The park’s long, pebbly beach is great for a relaxing stroll, and if you’re into birdwatching, keep an eye out for ospreys and other wildlife that call this area home.
Don’t forget to pack a picnic—there’s plenty of room to spread out under the trees, and honestly, there’s nothing better than lunch with a sea breeze.
9. Mashomack Preserve, Shelter Island

Hop on a quick ferry from Greenport, and you’ll land on Shelter Island, home to Mashomack Preserve—a stunning area within Long Island that feels like a hidden world.
This massive nature preserve is packed with miles of trails that take you through forests, salt marshes, and along quiet coastline.
Keep an eye out for deer, foxes, and even bald eagles while you wander, and if you’re up for a longer hike, the Red Trail is a favorite for its incredible views of the water.
Mashomack is all about peace and quiet, so don’t rush it—this is the kind of place where you’ll want to just breathe it all in and let time slow down for a bit.
10. Southampton

Heading over to the Hamptons, Southampton is your next stop where you can expect an upscale town known for its laid-back beach vibes.
Coopers Beach is the star of the show here, with its soft white sand, gentle waves, and views of massive beachfront mansions that make it feel totally luxurious.
You can rent a chair and umbrella, grab snacks from the little beachside cafe, and spend the day just soaking up the sun—it’s no wonder this beach is regularly ranked as one of the best in the country.
After the beach, stroll through Southampton Village, where you’ll find fancy boutiques, cute coffee shops, and art galleries that give the town its classic Hamptons feel.
11. East Hampton

Just down the road, East Hampton brings its own kind of magic, as it’s known for its natural beauty and that classic Hamptons elegance.
Main Beach is the go-to spot, with wide stretches of sand, rolling dunes, and lifeguards on duty—perfect if you’re in the mood for a swim or just want to relax with the sound of the waves.
For a dose of history, check out the Home Sweet Home Museum, a charming 18th-century house that’ll give you a peek into colonial life, or wander the historic village green, surrounded by old windmills and gorgeous homes.
And if you’re a foodie, East Hampton is a dream—grab breakfast at the ultra-cozy Golden Pear Cafe or splurge on dinner at Nick & Toni’s, where the wood-fired dishes are practically legendary.
12. Montauk

The next stop on the itinerary is Montauk, a beach resort located at the very tip of the island, known for its beautiful beaches and rugged coastal beauty.
Montauk Point State Park is the main event here, home to the iconic Montauk Lighthouse—the oldest in New York—and some seriously stunning views where the Atlantic Ocean and Long Island Sound come together.
Take a hike along the park’s trails for cliffs, rocky beaches, and maybe even a seal sighting in the winter months, or just climb up to the lighthouse for panoramic photos that’ll make your friends jealous.
Before you leave, swing by one of Montauk’s seafood shacks like Gosman’s Dock for a lobster roll, or end the day by heading to the beach to soak up the chill Montauk vibe one last time.
13. Fire Island

If you’re craving an island escape with no cars and a whole lot of fun, Fire Island is the spot to hit.
This barrier island is all about sandy boardwalks, cute little beach towns, and wide-open beaches where you can really unwind—Robert Moses State Park and Watch Hill are two favorites for soaking up the sun.
Don’t miss the Fire Island Lighthouse, where you can climb to the top for sweeping views of the Atlantic and maybe catch a glimpse of the NYC skyline on a clear day.
Whether you’re grabbing a drink at Flynn’s in Ocean Bay Park (closed over the winter, re-opens in May) or biking through charming towns like Ocean Beach, Fire Island feels like a summer daydream you won’t want to wake up from.
14. Jones Beach State Park

Wrapping things up closer to the city, Jones Beach State Park is a Long Island classic and one of the most iconic beaches in New York.
This spot is all about big sandy beaches, a massive boardwalk, and plenty of space to throw down a towel and dive into the waves.
If you’re into live music, the outdoor Jones Beach Theater hosts amazing concerts all summer long, with big-name acts performing right by the water.
There’s also mini golf, snack bars, and even a nature center, so whether you’re here to swim, chill, or explore, Jones Beach has a little something for everyone.
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