The elder son of Rear Admiral Yates Stirling, he was an outspoken advocate of American sea power as a strong deterrent to war and to protect and promote international commerce.

His younger brother, Commander Archibald G. Stirling (1884–1963) (United States Naval Academy Class of 1906) retired in 1933 but returned to active duty from 1942 to 1945 during World War II.

The first were Rear Admirals Thomas O. Selfridge Sr. and Jr. As a boy living in Baltimore's upper west side, Stirling attended public schools where, despite a professed dislike of physical combat, he had a reputation of being a fighter.

[8] During his father's cruise absences, the family's only knowledge of his well-being came in bulky packets of letters arriving in bunches over long intervals that Stirling's mother, Ellen, would read aloud to her children.

"[s]queezing out tar on every handhold to prevent being blown out into space by the great force of the wind and the pressure of the solid sheets of rain", Stirling climbed up two vertical shrouds and Jacob's ladders to the top gallant yard, 120 feet above the deck.

Succeeding in furling the sails and lowering the yards by "exerting every ounce of strength we could muster and while the gale was at its height", Stirling wrote in his memoirs forty years later, "The physical condition and the confidence acquired that enable you to hang, without batting an eye, by one hand in space with a yawning drop below you are things the modern sailor never attains.

Applying himself to ensure his standing would be high enough to be offered a commission, he improved his academic ranking that year and graduated from the United States Naval Academy on June 3, 1892, twenty-second in a class of forty.

"[20] Observing the miscegenation of whites with the indigenous Hawaiians during the few weeks his ship was at Hawaii, he later wrote in his memoirs, "I found them most wholesome companions, although I had the feeling that I must be careful not to fall in love.

"[20] Stirling's nineteenth century ethnic and cultural beliefs aside, he noted the geopolitical undercurrents of the importance of Hawaii to the United States, Great Britain and Japan as each maintained a naval presence.

[22] At Acapulco Bay, Mexico, "celebrated for its man‑eating sharks", Stirling was visiting Charleston and accepted the challenge of the Catholic chaplain, Father William H. Reaney, to swim off the anchored ship.

[23] During the voyage around South America and through the Straits of Magellan, the ship made ports of call at Callao, Peru, Valparaiso, Chile and Montevideo, Uruguay to show the flag and cement generally good relations "where considerable American gold was spent" and where the local officials lavishly entertained the Admiral and officers.

Charleston's captain, Henry F. Picking, due to his rank, became senior officer of the foreign navies in port and by international custom was regarded as the leader in concerted actions.

While Stirling was "foolishly exposing myself to stray bullets", a well-dressed man approached and introduced himself as a Brazilian naval officer and ordnance expert, just returned from England on a British merchant ship.

Ordering the coxswain to steer in close to the seawall for the Brazilian to jump off, Stirling told his passenger, "A word to the wise is sufficient" and wished him good luck.

On 23 February 1900 he joined the USS Celtic (AF-2), and on November 21 of the same year, reported for duty to his father, then a captain and the commandant of the Naval Station, San Juan, Puerto Rico.

Detached from the Naval Academy in June 1908 he next served on the USS Connecticut (BB-18), flagship of Admiral Charles S. Sperry Commander in Chief, Atlantic Fleet as gunnery officer.

Sailing from Hawaii, the fleet made ports of call at Auckland, New Zealand; Sydney and Melbourne, Australia; Manila, Philippines; Yokohama, Japan; Colombo, Ceylon; arriving at Suez, Egypt, on 3 January 1909.

While the fleet was in Egypt, word was received of a severe earthquake in Sicily that presented an opportunity for the United States to show its friendship to Italy by offering aid to the survivors.

[38] In April 1915, Stirling along with Assistant Secretary of the Navy Franklin D. Roosevelt and Admiral Bradley A. Fiske appeared before Congress concerning the deplorable condition of the Atlantic submarine fleet.

"[45] Stirling authored a comprehensive article on the modern history, design, operation, and strategic applications of the submarine and submersible for the United States Naval Institute Proceedings in July 1917.

The two smallest gunboats, USS Guam and Tutuila with the shallowest draft, could reach Chongqing year-round, including the winter when the river depth decreased by as much as thirty feet.

Stirling detached from the Yangtze Patrol in April 1929 and upon his return to the United States, was appointed president of the Naval Examining Board, Navy Department, Washington.

Stirling's strong belief in the guilt of the five Native Hawaiian men charged with rape and assault of a young naval officer's socially prominent wife was well-known, as was his displeasure at the result of a mistrial.

Stirling's public statements concerning the Massie Trial would be impolitic and offensive by current social standards nearly a century later; however, they were mostly supported by the contemporary mainstream media, the Navy and Washington.

Stirling recalled that his last connection to the Third Naval District was in the closing months of the First World War when he was chief of staff and "trying to put the one-year-old chicken back into its eggshell— that is demobilize".

While he was commandant at New York, Stirling's official duties saw him frequently receiving foreign dignitaries, including Air Marshall Italo Balbo during the famed Italian aviator's widely covered 1933 trans-Atlantic crossing with twenty-four Savoia-Marchetti S.55 seaplanes for the Chicago Century of Progress.

"Through the support of men of means who were Navy admirers, I gave to General Balbo and his officers a most elaborate dinner at the Columbian Yacht Club on the Hudson River, now demolished in the development of the Park project.

Speaking before the national convention of the Veterans of Foreign Wars in Philadelphia that year, Stirling warned that "the framing of neutrality laws to keep us out of war—without taking into consideration the terrible result to us of a dictatorial victory—is like 'whistling in the dark' or 'fiddling while Rome is burning.

In 1942, he advocated building a fleet of small, wooden, V-bottom, 30–60' long craft, capable of 30 knots, with two machine guns and six depth charge racks, manned by 3 to 7 men, to patrol the 35,000 miles of U.S. coastline and protect shipping.

RADM Stirling was a hereditary companion of the California Commandery of the Military Order of the Loyal Legion of the United States by right of his father's service in the American Civil War[69] having been elected to membership while an ensign in 1899.