Last weekend, Untapped New York Insiders had the unique opportunity to sail around New York Harbor aboard a 19th-century ship from the historic fleet of the South Street Seaport Museum. As we enjoyed a 2-hour private charter on a breezy and sunny afternoon, Insiders photographed iconic landmarks, helped the crew raise the sails, and enjoyed some snacks. Check out photos from our excursion below and join us for the next Insider experience by becoming a member today!

Schooner Pioneer

The 1885 Schooner Pioneer is the sole surviving example of an iron-hulled cargo sloop. Only two were ever made in the United States. Pioneer launched as a sloop from Marcus Hook, Pennsylvania, the center of iron shipbuilding, in 1885. She originally carried sand and other materials along the Delaware River and later hauled coal, lumber, bricks, and oil.

After being restored in the 1960s, the ship was donated to the South Street Seaport Museum in 1970. Pioneer is part of a fleet that includes the Mathilda, the Wavertree, and the tugboat W.O. Decker which we waved to on the water!

Tugboat W.O. Decker

During our sail, Insiders captured stunning shots of other vessels on the water and New York City’s skyline. We saw views of the Freedom Tower, the Statue of Liberty, Governors Island, the abandoned hospital on Ellis Island, the Brooklyn Bridge, the Battery Maritime Building, and much more.

Perhaps the most exciting part of the sail was when our Insiders got to become part of the crew! Our very own Chief Experience Officer Justin Rivers joined a group of intrepid (and strong!) Insiders in hoisting the sails. Taking direction from our Captain and the rest of the amazing crew, they heaved ho and unfurled the sails so we could ride the wind.

You can sail aboard Pioneer or the tugboat W.O. Decker by joining a public sail with the South Street Seaport Museum from May through October. Learn more and see the upcoming sail schedule here!

Check out all upcoming Untapped New York Insider events here! Use code JOINUS and get your first month of membership free. As an Insider, you gain access to member-exclusive events, like this private charter, free virtual experiences, and our archive of 250+ on-demand webinars.