Twice the thirty-first President of the United States came close to Martha’s Vineyard, into Vineyard waters, once a few weeks after his first inauguration in 1933 when he skippered the yacht Amberjack II into Edgartown harbor and lay overnight, and again in August 1941, when on the yacht Potomac, bound for the meeting with Winston Churchill which resulted in the Atlantic Charter, he kept rendezvous at Tarpaulin Cove.
On the second visit little could be said. Radio and press kept silence, and even after the announcement of the meeting between Mr. Roosevelt and Mr. Churchill “somewhere in the Atlantic” the details of the trip came out slowly and piecemeal. But it was in Vineyard waters that the President met and boarded the Augusta for the great enterprise.
The first visit was recorded for the Gazette by Joseph Chase Allen and his report is reprinted here, in part for the memory of an occasion of the peaceful days when no one could foresee the stress, catastrophe and dearly won victory which lay ahead. The President himself must have looked back many times upon that carefree summer cruise, and Vineyarders like to hold it in recollection.
In the Gazette of June 23, 1933, Mr. Allen wrote: 
President Franklin D. Roosevelt, the nation’s first real seagoing chief executive, made port at Edgartown Sunday afternoon in the midst of the nor’west squall, and lay there at anchor until the following morning when he got under way for Nantucket. The visit was entirely impromptu, weather conditions making it highly practical that he seek shelter, and the President did not himself land, although invitations to remain overnight ashore were extended to him. But his son James landed and made the acquaintance of the town, exchanging friendly remarks with various person he met.
Watchful eyes were directed seaward during the entire day, and the approach of the Amberjack II was observed as soon as she made West Chop on her run out of Woods Hole. Charles Ellis, assistant lightkeeper at the chop, stood by the reservation flagstaff, it being Keeper James Yates’s day off, and dipped the colors as the President’s yacht and escorting destroyers sped past, receiving a return salute from the destroyers’ sirens. This was the President’s first Island greeting. The shores and headlands were quickly dotted with people who sped to these points of vantage to watch the progress of the yacht past the Island, and it was a sight that drew more than one complimentary remark from the older men who continue to take a man’s measure by his ability in seamanship.
Dark, lowering clouds rolled across the heavens, with a light spot here and there to relieve the gloom. The water was dark and flecked with foam. Against this dark background sped the little schooner, a single reef in her mainsail, foresail and forestaysail spread and hard filled, leaning to the fresh nor’wester that breezed on her starboard quarter. Her fisherman’s bow hung slightly lifted, for the sea was smooth, and a broad streak of her copper showed amidst the foam that flung from her forefoot. “Logging a good nine knots,” said an oldtimer. “The old man’s carting canvas.”
And then the first squall struck with increasing wind that whistled along the bluffs, bringing a torrent of rain and thickening the mist that hung over the water. It was no surprise to the seawise watchers when the Amberjack hauled on the wind and headed for Edgartown. Any one of them would have done the same, and respect for the navigator’s sagacity heightened as they observed the move.
At Edgartown the lower streets and wharves were quickly sprinkled with spectators, coming and going. Newspaper representatives scurried to and fro. Boats sped from shore through the rain, and others from the destroyers circled in ceaseless patrol about the anchored yacht, while telephone and telegraph wires burned hot between the Vineyard and the mainland, as the nation was notified that the President had come to anchor in Edgartown harbor.
And amidst it all, the President was on deck, clad in his dripping oilskins, looking over the schooner’s gear and rigging, exactly as any fishing skipper would have done, the calmest man in sight, and again the oldtimers breathed a word of admiration. For everything was snug on deck, sails properly stopped, sheets and halyards coiled down, and all things shipshape before the President went below.
No one among Island officials visited the President’s yacht. Apparently all were of the same mind regarding this matter, for those who were questioned on the subject flatly refused to consider it.
“The man is trying to rest,” said one, “and the Lord knows he needs it.
Although many Islanders from all towns visited the Edgartown wharves, none stayed long and at no time was there a vast throng as intimated by mainland newspaper dispatches. A few boats went within respectful distance of the Amberjack, but no one attempted to be nosy, and the Vineyard population afloat and ashore was disposed to respect the President’s vacation privacy.
The President got under way on schedule on Monday morning, leaving Edgartown between 6 and 6:30. There were no crowds to see him off, but plenty of Islanders were normally astir at that hour and watched the Amberjack and the rest of the fleet depart.