Thinking about next July and our trip to Portland Harbor, here in the early 60's. The schooner is the Portland Pilot, built on Brown's Wharf in 1931, converted to a windjammer in 1971 as the Timberwind, once again in Portland as a daysailer.
The white one astern of her is a "311" the USCGC Barataria WWII seaplane tender serving in the Coast Guard for Atlantic weather station duty. Her home port was Portland from 1949 to 1967.