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Pilot schooners in the pre-Civil War period were small- to medium-size schooners (60 to 90 feet on deck) which transported pilots to inbound vessels and picked up pilots from outbound vessels. Their presence was indicated by a signal flag hoisted on the main mast. In Boston, the pilot flag was blue and white, divided vertically. In New York, the flag was solid blue, sometimes with stars in rows. Other ports had pilot flags of differing designs.
When a merchant ship approached its destination port, it was (and still is) mandated by law to take on a pilot to guide the ship through unfamiliar channels, tidal currents, and other hazards to reach safe anchorage or berthing. The same law applies to outbound ships, which must take on a pilot to guide the vessel safely, leaving the pilot with a stationed pilot schooner once the port is cleared. The small rowing boat used to transfer the pilot from schooner to ship (or ship to schooner) was called a pilot yawl (in New York) or a pilot canoe (in Boston).
In many American ports, piloting could be a very competitive business, with rival schooners racing to an inbound ship to be first to put a pilot on board. These vessels were sometimes sold out of service to become yachts, while yachts were occasionally sold into pilot service, so adapted for speed were both types.
– Erik Ronnberg
Tom Cunliff, Pilots 1: Pilot Schooners of North America and Great Britain (Douarnenez, France: Le Chasse-Maree/Maritime Life and Traditions; and Brooklin, ME: Wooden Boat, 2001).
Johnson, H. and Lightfoot, F.S.: Maritime New York in Nineteenth-Century Photographs, Dover Publications, Inc., New York
The New York pilot boats would sail out to meet large incoming ships, flying the blue and white flag. The pilot would board the large ship and guide her into harbor. On outgoing trips the pilot boat would pick up the pilot after the ship in his charge had cleared the harbor.