Sailo Sunset Cruise Around New York City

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After my 2 month summer internship with Sailo in New York City, I decided to persuade as many friends as I could to come and visit me and what has always been my favorite city. One of the reasons it is my favorite, is the ease to escape the hustle and bustle of Manhattan by simply crossing a bridge, or hopping on board of a boat rental in NY, and viewing it from afar. After gathering a group of 6, I excitedly planned various activities for them for their 10 day visit. I knew from the beginning that I wanted to take them on the water, but was waiting for the right moment to pitch the idea.


In turn, as well as planning things for them, my friends also gave me ideas of things they wanted to do, and to my luck, one day whilst chatting one of them said ‘Tom and I are going to book the Liberty Island cruise, I know you’ve done it before so you don’t have to join us’. My face lit up with joy, ‘Give me a day’ I replied.


I came back to the group after a day, having spoken to Walter, one of the many lovely boat owners in New York that we work with at Sailo, and a plan for all of us. I sent out my message with such pride ‘Boys and girls, I’ve booked us a 2 hour sunset sail around New York City Harbour on our own sailboat, for nearly the same price as a large tourist cruise, trust me, it will be worth it’.


As none of them had done anything like it before, they responded with small thanks, cheers and intrigue; they had yet to realize just how lucky they were. I, having done the sail before, knew they were in for real once in a lifetime experience that they could take home with them.


My friends and I gathered from various corners of Manhattan at Pier 40 at 6.30pm, snacks and drinks in hand, ready for our sail on his beautiful sleek sloop. Walter greeted us with a tremendous smile, and helped us on board for our sunset sail. Conversation flowed as we swiftly sailed down the Hudson river towards the Financial District and Governors Island. We had picked the perfect time to sail, as we moved down towards New Jersey and the Teardrop Memorial just as the sun began to set. There had been patchy rain earlier in the day which scared us all a little, but by sunset it had subsided and created the most beautiful red glow against the clouds as the sun sank into the sea.


As it grew darker, we started to sing; having no speakers didn’t stop us, as we all bellowed classic songs together at the top of our lungs. We made sure we hadn’t scarred Walter, but he was extremely happy to see us having such a good time. As it became completely dark we calmed down, a few of us sat on the bow and a few on the stern, watching the lights of the skyline twinkle on the river.



As we turned around around by the Brooklyn Bridge, reminiscent of my summer in the city, I slowly began to sing New York, New York as we passed the Freedom Tower and returned to dock, shedding a small tear. As we docked, I’d never seen so many large smiles grouped together. Everyone was thrilled with their Sailo experience, and our sail held some of their favorite moments of the entire 10 days. I was delighted everyone had had such a good time, personally I couldn’t think of a better way to truly experience New York City in all its glory.

Looking for a memorable experience like Natalie’s? Check out our sailboat rentals in NY and plan for a sunset cruise to remember!