Long Island Vacation Destinations

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It’s no wonder that Long Island is one of the most popular vacation destinations on the East Coast! It offers vacationers beautiful white sandy beaches, majestic rocky bluffs, park land, art, science and history museums, theatres, vineyards & wineries, restaurants, unique villages and towns, and so much more!

Stretching approximately 115 miles from the west end to the eastern tip of Long Island, each village and town has something unique to offer. For instance, there’s North Fork synonymous with wine tours, the Hamptons synonymous with beachfronts and celebrity homes, and then there are seaside villages like Greenport and Cold Spring Harbor, and Montauk for its clam bar restaurants and pristine land.

There’s no doubt that vacationing on Long Island will leave you with plenty to see and do. So no matter the season, plan your next vacation on Long Island with this Guide to help you!

For a Vacation with Kids
A vacation on Long Island can be a fun experience for all. There’s no need to settle for a vacation where only kids have fun or only adults have fun when you plan your vacation to include some of these spots and activities.

Kids Museums
When there’s no touching, feeling or interactivity the experience of a museum can be quite boring for the kids. Luckily, on Long Island, kids can let loose and have fun at child-friendly museums, exhibits and aquariums like:

Long Island Children’s Museum
11 Davis Avenue
Garden City, NY 11530

Enjoy hands-on and interactive exhibits that encourage exploration. There are permanent exhibits like Bricks & Sticks, Bubbles, Feast for Beast where you can see a menagerie of animals and even a fun play environment for tots called TotSpots for jumping, sliding, pretend play and so much more.

Maritime Explorium
101 East Broadway
Port Jefferson, NY 11777

It’s all about touching here! Kids can explore maritime and marine challenges from understanding volume to designing and building suspension bridges. There’s also microscopes and magnifying glasses to get a close up look at its shell and ephemera collections.

Railroad Museum of Long Island
440 4th Street
Greenport, NY 11944

If there are train lovers in the family, then a visit to this museum is a must! Get up close to a real train at a historic 1892 freight house.

Cold Spring Harbor Whaling Museum
301 Main Street
Cold Spring Harbor, NY 11724

If whale watching on Long Island is part of your vacation plans then complete the entire experience with a visit to this museum complete with over 6,000 artifacts that offers a view of the history of whaling in the Long Island region.

Long Island Aquarium and Exhibition Center
431 East Main Street
Riverhead, NY 11901

Let your eyes amaze you here with the sight of one of the largest all-living coral reef displays, a 120,000-gallong shark thank and more than 100 other exhibits of species under water. The museum also has outdoor exhibits like the koi pond, sea lion coliseum and much more!

Animal Watching
Long Island is surrounded three sides by bodies of water, so there’s plenty of opportunities to catch animals at sea!

  • Seal Watching – Seals on Long Island can be a fun experience for everyone. The fun critters can be seen through one of the many professionally guided tours and cruises. The best views are usually during the Winter and Spring.
  • Whale Watching – Whale watching on Long Island is typically an activity completed during the Summer. Catch a glimpse of marine life in the Long Island Sound, South Shore or out on the East End through a whale watching tour.

Fun at the Beach
Long Island has plenty of beaches for fun in the water or sand.

Sunken Meadow State Park
Rte. 25A and Sunken Meadow Parkway
Kings Park, NY 11754

In addition to a beautiful beach with playground fun and fishing options, it’s also one of the largest picnic parks on the Island.

Cedar Beach
Harbor Beach Road
Mount Sinai, NY 11776

In addition to a nice beach, there’s a fishing pier and nature path overlooking the Long Island Sound. Also head over to the Nature Center to learn about Long Island wildlife through touch tanks and other hands-on exhibits.

Jones Beach State Park
2600 Ocean Parkway
Wantagh, NY 11793

It’s no wonder this is a popular Long Island destination particularly in the summer. There’s a 6.5 mile ocean beach, swimming pools, miniature golf, playgrounds, and performing arts theater shows.

For a Vacation with Romance
Long Island has romance in the air with its beautiful scenic spots and plenty of restaurants and venues to help set the mood no matter the occasion. And when it comes to having a romantic vacation, there’s also plenty to do for lovebirds. 

Vineyard Tours
Why travel to the West Coast when you can learn about the art of wine-making and sample it all right on Long Island?! Find plenty of vineyard tours available, especially in North Fork, which has been dubbed the Napa Valley of the East, or Long Island’s Wine Country. Here you’ll find approximately 50 different vineyards. The Hamptons is also home to several vineyards.

Wineries Tours
Long Island is a premier destination for wine tasting. Enjoy special food pairings with your tasting choices and many spots also include live entertainment.

Whether you have a love for lighthouses or just want to be in a unique place, visiting one of Long Island’s lighthouses can help set the romantic mood. People enjoy it for its beauty and for the amazing views you get atop one of them. Many folks also host wedding ceremonies at the historic Montauk Lighthouse, a national historic landmark.

Romantic Dining
A romantic vacation isn’t complete unless it also includes romantic dining. Select from restaurants with a waterfront view or simply head to some of the top restaurants offering great food and a great dining experience like Graceful Rose Restaurant in Port Jefferson with stellar seafood and steaks, Volpe Restaurant in Woodbury with Italian cuisine with a twist, Rockwell’s Bar & Grill in Smithtown with a nice and friendly pub restaurant atmosphere, or the many other restaurants located on Long Island.

Fire Island
For an ultimate romantic getaway on Long Island, you’ll want to head to Fire Island where its free of cars and it simply puts you in another world that’s timeless and wonderful.

Greenport – “One of America’s Prettiest Towns”
Yes, Greenport – a little seaside village – was voted “One of America’s Prettiest Towns” by Forbes in 2011. Enjoy beautiful grassy land, a walk along the boardwalk, a ride on an antique carousel in Mitchell Park and great places to stay like the Cliffside Resort, which is literally located on a cliff overlooking the Long Island Sound.

For a Vacation with Cultural and Educational Experiences
The length of a vacation ultimately doesn’t matter. It’s the experiences you take away that matter most and in some case they can be quite eye-opening and educational.

Living History at Old Bethpage Village Restoration
1303 Round Swamp Road
Old Bethpage, NY 11803

On this 209-acre plot of land is a living history museum that takes you back to the 19th century. View the history of how homes, farms and businesses operated during that time.

Sagamore Hill National Historic Site
20 Sagamore Hill Road
Oyster Bay, NY 11771

One of America’s beloved Presidents had his home located on Long Island. Sagamore Hill was the place President Theodore Roosevelt called home from 1885 until his death in 1919. The home remains closed until July 2015 for rehabilitation. The location is also complete with nature trails and a picnic area.

Planting Fields Arboretum State Historic Park
1395 Planting Fields Road
Oyster Bay, NY 11771

This isn’t just a historic site, but a premiere arboretum. It is the former Gold Coast estate of the W.R. Coe family complete with gardens, woodlands, and nature trails. Visitors can expect a spectacular any time of season in the year.

Walt Whitman Birthplace
246 Old Walt Whitman Road
Huntington Station, NY 11746

Get to know one of America’s finest poets! A tour of Walt Whitman’s childhood home will offer more understanding to how he grew up as well as offer an opportunity to review his works of art in poetry.

Oheka Castle
135 W. Gate Drive
Huntington, NY 11743

Set your eyes on an amazing estate situated on 443-acres of land. Oheka Castle is on the National Register of Historic Places. It offers a view of historic architecture, wining and dining under a European ambience, formal garden, and a look into the life of Otto Hermann Kahn,m a financier and philanthropist. You can also say you visited one of the largest private homes in the U.S. after you’ve taken the historic mansion tour.

Long Island Museum of American Art, History & Carriages
1200 Route 25A
Stony Brook, NY 11790

Discover the rich cultural history of Long Island here! It contains historic pieces that go back to the early 1800s, including horse-drawn carriages.

Walk Around Town/Town Visitor Guides
If your time is limited and you just want to explore a part of Long Island in a day or two, there are a few places you definitely want to visit. These Town Visitor Guides will inform you of what you can expect.

North Fork
If you’re looking to head to Eastern Long Island, North Fork is one of the places you need to hit up. On top of wineries and vineyards, it also has pristine beaches, farmers markets, golf courses, an great attractions like Splish Splash.

Sag Harbor
Make a visit to one of Long Island’s hidden gems. Its village is complete with small town style shops and old buildings and houses, a number of which landed a place on the National Register of Historic Places. It also has plenty of nautical attractions where taking a sail or cruise is a must. While there, also catch a live theater performance at Bay Street Theater.

Yes, many recognize Montauk for the historic Montauk Lighthouse, but there are also many parks, including five state parks here! Boating and fishing should also be part of your plans – this home to one of the largest commercial and recreational fisheries, so you can expect to catch luke, bluefish, sea bass, striped bass, swordfish, and maybe even a shark! If fishing isn’t your thing, then just go with the sunset cruise to enjoy beautiful scenery.

The Hamptons
Here’s your chance to get in touch with the lifestyles of the rich and famous. The Hamptons offers wineries, vineyards, country clubs, dining, and nightlife fun!

Freeport Nautical Mile
Enjoy a vacation complete with waterside dining, nightlife fun, and a look back at Long Island’s maritime past.

Stony Brook
This place is home to many college students, but don’t think of it as a visit to a college town because there’s much more to it. A visit to Avalon Park and Preserve will have you enjoying the duck pond and hiking trails. There’s also Grist Mill, a national registered historic place that’s not far off.

Have a favorite Long Island vacation destination you don’t see here? Let us know!

Additional Resources for Vacations on Long Island

If you're looking for fun things to do in other great places on Long Island, check out our other Guides for Sag Harbor, The Hamptons, Ocean Beach, Fire Island, Northport, Greenport, Port Jefferson, Montauk and North Fork!