Long Island is a peninsula southeast of New York state. Brooklyn and Queens are part of the peninsula but usually we mean the eastern part -Nassau in the center and Suffolk in the east- if we are talking about Long Island.
Long Island starts at New York Harbor (mouth of the Hudson River), and it is about a 200 km (about 124 mi) drive to the Hamptons on the shores of the North Atlantic Ocean. People visit Long Island year-round because of the beautiful beaches, vineyards, Gold Coast Mansions, and charming towns. A lot of reasons to lose your heart on Long Island.
Transportation
I rented a car at JFK airport to drive to Hauppauge. (Phonetic: “hawp‑hawg”). A hamlet in the center of Long Island. I chose the location so I could drive to all angles in about 1 to 2 hours. JFK, laGuardia Airport, and some smaller airports are on Long Island. Be aware that many New Yorkers head to the coast on weekends, so especially with sunny weather it can be busy on the roads.
There are good train connections too but due to the places I wanted to visit, I decided to go by car.
Where to stay
After some time in New York with my daughter’s family in Brooklyn, I had to get used to a new daily rhythm. The swimming pool, at the Airbnb where I stayed, helped a lot. Great to start the day with some laps.
“My Happy Place” in Hauppauge is an excellent Airbnb location. Hospitality and a swimming pool contribute enormously to this. If I wanted to drive to the coast, it would take 20 minutes to half an hour and to the east about 1 hour. My wish to be in the center of Long Islands attractions came true.
There are hotels, holiday homes and Airbnb properties, all over the Island. In many price ranges and in many styles. So, decide what is important for you and start looking for the perfect fit. For example, for me it was the location and a pool!
What to visit
Sag Harbor (Southampton, East Hampton)
My goal: visit John Steinbeck’s house in Sag Harbor. More about Sag Harbor and John Steinbeck: here
The town itself is lovely, not too big, with an atmosphere reminiscent of small coastal towns in Southern France. Lots of reed (cane, thatch), white, verandas, flowers, nice shops and of course the American flag. Sag Harbor was a major port for the whaling industry and part of the Harbor Fest in September are whaleboat races.
The village of Sag Harbor is in the Towns of both Southampton and East Hampton. Visit Mainstreet with the lovely shops, take a walk along the waterfront, do not forget to take a picture of the mill, lunch or dine in one of the nice restaurants, shop books, clothes, liquors, or interior design and enjoy the atmosphere.
Greenport and a vineyard
Greenport (first settled in 1682) was once a whaling and ship building village, and since 1844, has been the eastern terminal station on the north for the Long Island Railroad. In the Northern part of Long Island, there are lots of vineyards. So, a combination of a charming village with a visit to a vineyard is a great option.
The road there leads the last 17 miles through a beautiful agricultural area, not only vineyards but also dairy farms, lamb, and beef farms, and along the road flowers (in September many sunflowers) and apples. Buckets full of bright red apples.
With the music of “La La Land” I enjoy driving past the greenery and farms. I turn a bend and suddenly I see the bay. It wasn’t dramatic, but it felt like a delightful surprise! On the way back along the same green road, I looked in alarm at two deer on the road. One small and one a little larger a little further on. Suddenly I understood those ‘deer crossing’ signs in a whole new way.
As people write about Greenport Village, “everything you find in the Hamptons, but without the pretension,” that is true, but sometimes I find that a bit sparse. For example, it is Labor Day weekend, but some coffee shops are not even open, and the most advertised terraces are not open until 11:30. That surprises me about a place like this. But the photogenic makes up for a lot!
Vineyard
The next plan is to visit a vineyard. I thought, in advance, that I would go to Harbers, but on the road to Greenport I can already see that it is more of a family park. I pass a vineyard with the name “One Woman Wines and Vineyard,” which is very appropriate for this trip, so I tasted a Grüner Veltliner there and bought a bottle. If you go alone and have to drive, it’s best to buy wine to enjoy afterward.
Cedar Beach Nature Preserve
On the North side of Long Island, you will find Cedar Beach. A beautiful place for Fishing (not that I know anything about fishing, but this is where it is known for).
The water is called: The Long Island Sound, it’s a semi enclosed arm of the North Atlantic Ocean, lying between the New York–Connecticut (U.S.) shore to the north and Long Island to the south. Calmer water than in the south, where you can experience extraordinarily strong waves.
Cedar beach is a beach with a lot of stones, but because I really enjoy swimming, this is a suitable beach for me.
Fire Island
To an island (via something like 2 large Zeeland bridges). The beach is impressive in its vastness (even the parking lot is incredibly large) and the waves crash on the shore. Unfortunately, the bugs arrived too. A woman beside me had at least 10 on her leg. She says they come when the wind comes from the north. I cannot keep it up for long, partly because I didn’t dare go far into the sea. The power of those waves is so intense and yes, if you go on holiday alone, no one misses you very quickly, so I stayed in the surf!
I also want to take the walk to the lighthouse before 12 o’clock because with 33 degrees C it is a hot day again. The walk is beautiful, the volunteers at the lighthouse are enthusiastic, and the climb of 187 steps is doable. More about Fire Island coming soon!
Port Jefferson
The first day on Long Island there is only one thing on my mind, fish, chips, and a Chardonnay on a terrace overlooking the water or a harbor. In Port Jefferson I will find where I am looking for at Danfords Hotel and Marina. Ferries to New England and Connecticut create a lively atmosphere at the harbor with people, cars and sometimes bicycles coming and going.
Bonus Tips
🌿 Travelling on your Own in Your Sixties? Yes You Can!
Pack light but smart
Stay flexible with transport
Know where you’re staying
Talk to locals
Let someone know your plans
Trust your gut
- If you are interested in interiors, you of course know the Hamptons as a luxurious coastal style (more about that style in my article about “Interior style Beach house / coastal” or read “How to make an interior design mood board.”
- I forgot to ask it myself but there are often senior rates.
- Goop, are you a fan of Gwyneth Paltrow’s Goop platform? There is a Goop shop in Sag Harbor.
Books with Long Island references:
- John Steinbeck, Travels with Charley, in search of America. More about John Steinbeck and his Sag Harbor retreat here.
- Geert Mak, reizen zonder John, op zoek naar Amerika
- Colson Whitehead, Sag Harbor
All kinds of things happen on the beach: From a Reading to Trump propaganda.
Lot to make you lose your heart on Long Island!
