Antonio Jacobsen spent his free time at New York’s harbor and along the Hudson River, painting pictures of vessels as small as tugboats and as large as transatlantic liners. A close look at this painting of the tugboat May McWilliams shows the captain in the top cabin at the front of the vessel and a single passenger at the rear. Harbor captains used tugboats as early as the 1700s to escort larger ships through narrow or complicated passages.