Welcome to our Jersey Gypsy column, where our resident travel reporter, Valentina, roams the globe in pursuit of stories.
If you need a quick getaway, Long Island is just an hour’s drive from the city. It’s the perfect escape from the hustle and bustle of the city that never sleeps. You don’t have to leave the state to enjoy beautiful beaches and scenic vineyards for a relaxing vacation.
Having toured Florida, I honestly wasn’t expecting much from my Long Island trip, but my experience left me thoroughly surprised. My visit to Long Island was delightful, and here’s everything I did.
Long Island’s Must-See Destinations
- Pindar Vineyards – Ideal for wine lovers
- Jones Beach State Park – Perfect for beach relaxation
- Oheka Castle – A taste of Gilded Age grandeur
- Fire Island – A peaceful island escape
- The Hamptons – Elegant beaches and charming towns
- Montauk Point Lighthouse – Historic views and scenic hikes
Vineyard Hopping: The Wine Trail
Okay, I can’t resist starting with a little wine-fueled adventure. Long Island’s Wine Country, particularly the North and South Fork, is a haven for oenophiles.
I started my vineyard hopping at Pindar Vineyards, one of the largest on the East Coast. The sprawling estate, with its rows of neatly planted vines and a charming tasting room, was the perfect introduction to Long Island wines.
I tried their award-winning wines, including a crisp Sauvignon Blanc, a fruity Chardonnay, and a unique blend called Autumn Gold.
Next up was Macari Vineyards. This family-owned winery focuses on sustainability, and I joined a tour here. The vineyard was stunning, with great views of the Long Island Sound.
Of course, the tour wouldn’t be complete without a tasting, and it did not disappoint. I tried their Chardonnay and rosé, both delightful.
Visiting Bedell Cellars in Cutchogue was also a great experience. A boutique winery focused on handcrafted wines, the tasting room was cozy, and I was particularly impressed with their sparkling wines. They were crisp, elegant, and perfect for celebrating any occasion.
Don’t worry, I also indulged in some of their other drinks. What stood out to me was the First Crush White. It was crisp, fruity, and citrusy, making it incredibly refreshing.
Jones Beach State Park
After my wine-fueled adventures, I headed to Jones Beach State Park. Yes, there’s more than just the Hamptons if you’re looking for a beach break in New York. Jones Beach is a sprawling coastal oasis with pristine beaches, an iconic boardwalk, and a variety of activities. It’s the perfect place to spend a day (or two, or three…).
I started my day here with a leisurely stroll along the boardwalk, soaking up the sun and enjoying the ocean breeze. The boardwalk is lined with shops, restaurants, and even a mini-golf course.
The sand at the beach was soft and white, the water crystal clear, and the waves were gentle – perfect for swimming, sunbathing, or just relaxing with a good book. I even tried stand-up paddleboarding, which was a fun (and slightly wobbly) way to experience the beauty of the coast.
In the afternoon, I joined a guided kayak tour of the nearby salt marshes. We paddled through calm waters, spotting herons, egrets, and other wildlife. Our guide, a local naturalist, shared fascinating insights into the ecosystem and the history of the area.
Oheka Castle
Okay, history buffs and architecture enthusiasts, this one’s for you. Oheka Castle is a magnificent Gold Coast mansion that will transport you straight back to the Gilded Age. This opulent estate, once home to financier Otto Hermann Kahn, is now a luxury hotel and event space.
I joined a guided tour of the castle and was blown away by its grandeur and opulence. We wandered through the lavishly decorated rooms, admiring the intricate details, antique furniture, and stunning artwork. The ballroom, with its soaring ceilings and crystal chandeliers, was particularly breathtaking.
The castle grounds are equally impressive, with manicured gardens, fountains, and even a reflecting pool. I strolled through the gardens, imagining the lavish parties and gatherings that once took place here.
Just like my nostalgic visit to the oldest city in America, I was transported back in time and had a fascinating glimpse into the lifestyle of the rich and famous during the Roaring Twenties.
Fire Island
Of course, I went to the Hamptons, but before that, I felt like I had to check out a beach outside of that area. I learned about Fire Island when I was researching Long Island. It’s a unique barrier island accessible only by ferry, offering a laid-back atmosphere, which is exactly what I was looking for.
I took the ferry from Bay Shore and arrived in Ocean Beach, a charming village with colorful houses, quaint shops, and a lively boardwalk. From there, I rented a bike and explored the island.
I also spent some time at Robert Moses State Park, a beautiful natural area with beaches, dunes, and hiking trails.
The Hamptons
I have to agree now that no trip to Long Island is complete without a visit to the Hamptons, the playground of the rich and famous. But it was delightful to discover that this place is more than just mansions and fancy cars. They also have stunning beaches, charming small towns, and a laid-back vibe that’s surprisingly accessible.
I first went to Southampton, where I saw some historic houses, art galleries, and upscale boutiques. Strolling down Main Street felt good. I mostly window-shopped and admired the beautiful architecture around me.
I also decided to explore East Hampton. It’s another charming village with a mix of historic and modern architecture. In this area, I visited the Pollock-Krasner House and Study Center.
I wasn’t expecting the place to look so homey, but it made sense because it used to be the home and studio of abstract expressionist painters Jackson Pollock and Lee Krasner. It was fascinating to see where these iconic artists created their masterpieces.
Montauk Point Lighthouse
Even though I agree that Long Island is mostly great for its beaches and wineries, I just had to visit the Montauk Point Lighthouse. I’d heard about it before since I’m a sucker for historical landmarks. It was built in 1796, making it the oldest lighthouse in New York.
I climbed to the top of the lighthouse. The 137 steps didn’t sound like much, but I was catching my breath when I reached the top. Totally worth it for the panoramic views of the Atlantic Ocean. It gave me a sense of awe at the power and beauty of the sea.
Since I was there, I decided to hike along the cliffs. It wasn’t planned, but I made sure to wear comfortable shoes just in case. I also visited Montauk Point State Park and the museum, so I could completely immerse myself in the place’s rich history.
Crossing Off My Long Island Bucket List
I’m glad I took the time to see what Long Island is truly about. Sure, the beaches and wineries made my whole adventure fun, but I still think it’s a region full of surprises.
I now understand why it’s one of the places New Yorkers escape to when they need time away from the busy city. It’s not too far, just an hour away – yet it feels like a completely different world.
While I think I’ve explored some great places in this part of New York already, I’m sure there is still a lot to see, especially the beaches and wineries. I’ll definitely go back for more glasses of wine there.
Long Island Bucket List – FAQs
How Can I Get to Long Island?
There are plenty of ways to get to Long Island, including by car, train, air, ferry, and bus. If you’re coming from New York City, you can take the Long Island Expressway (I-495), and it usually only takes about an hour’s drive.
When’s the Best Time to Visit Long Island?
The best time to visit Long Island is from March to May or during spring when the temperature is mild and the flowers are blooming. It’s also when the beaches are less crowded compared to summer (June to August).
Is Long Island Expensive to Visit?
Long Island can be expensive if you’re staying in the Hamptons and mostly visiting fine-dining restaurants. However, there are plenty of budget-friendly options too. You can visit state parks for camping, stay in hostels, and explore less touristy areas that offer better prices.
