Sailing Jamaica Bay

Sailing Jamaica Bay

So, the mini-mermaid got me a birthday gift, and it was hard to schedule because we have busy lives, but we finally got a date and me and the mermaid and my mini-mermaid and her merman went out sailing with Sail Rockaway out of the 59th Street marina. Now, I have never been to this marina, and I was flabbergasted at how cool this place is. There were rows of boats, with many being house boats, and there was even a boatel if you will, a boat hotel. I mean, how come I never knew about this? But the mini mermaid certainly did. She booked a sunset sailboat ride for the four of us and we got on this cool little sailboat and went out onto Jamaica Bay on a soft, beautiful August night.

Rockaway looks completely different from out on the water. It was high tide and the marshes were only showing off their tops. The seagulls, mostly laughing gulls, were in their glory circling around and eating everything in sight. There was a cool breeze, and no mosquitos, and there were blue herons and snowy egrets all around. In the trees on shore were ospreys that were so big they looked like eagles.

We glided through JoCo marsh into the channels and went in and out of several lanes of marshes. The water was warm and we watched the jumbo jets float overhead as the ruby red sun was setting below the clouds. Pure magic I tell you. Our skipper, Sean, knew the ins and outs of the marshes, the names of all the birds, and brought us to within yards of the JFK runaway. I’d never imagined that JFK was so close and that the back bay was so beautiful. As the sun set, we came back around toward Far Rockaway and the beauty of this large body of water. Our skipper talked about the sting rays, dolphins, striped bass, and sometimes sharks that called these waters home.

Looking back at the Cross Bay Bridge and the buildings that dot the Rockaway peninsula, I thought how different it looked from this vantage point, and how lucky we were to experience that viewpoint. I wondered how this might have looked to the Lenape Indians that lived here and fished these waters well before any airplanes flew overhead. I thought about those rum runners during prohibition who used the bay as their personal playground bringing in booze to the underserved. And I thought, there are many on the peninsula who feel slightly overserved!! I guess we all know someone like that, present company included!

As we headed back to the marina, we saw the twinkling lights beckoning us back to our mooring. We thanked our skipper for a special night and found he was headed to Fiji for a month of sailing there. I thought that this guy has the right idea. When we departed the gated area, we had to drive past a flooded entrance, high tides still impact this part of the peninsula disproportionately. We encountered a few more streets that somehow were flooded by the high tide. My guess is that the sewer systems have not been properly adjusted here.

The evening was magical and I recommend that if you have not had this experience yet, you should take advantage of the opportunity before the summer is over and get out on the water and see life from a different perspective, it will make all the difference in the world!

For your own sailing experience, head to: www.sailrockaway.com

2026 Summer Guide