Operation Sail refers to a series of sailing events held to celebrate special occasions and features sailing vessels from around the world. Each event is coordinated by Operation Sail, Inc., a non-profit organization established in 1961 by U.S. President John F. Kennedy, and must be approved by the United States Congress. Often referred to as OpSail or Op Sail, the event has the goals of promoting good will and cooperation between countries while providing sail training and celebrating maritime history. It is also sometimes erroneously referred to as "Tall Ships". While the tall ships form the centerpiece of the event, smaller sailing vessels also participate.

Op Sail events, when scheduled, are run concurrently with the annual International Naval Review, which features present-day warships from various navies. Six Op Sail events have been held to date, in 1964, 1976, 1986, 1992, 2000 and 2012. The event culminates in the Parade of Ships on the Hudson River and in New York Harbor on July 4, Independence Day. The United States Coast Guard cutter Eagle has been the host vessel to all six Op Sail events.

Along with Nils Hansell, Frank Braynard launched the world's first Operation Sail, an extravaganza in which tall ships and naval vessels filled New York Harbor, in 1964.

The inaugural Opsail was a tie-in with the 1964 New York World's Fair. Operation sail 1964: Four years in the making, Operation Sail is an international effort to promote goodwill and to generate awareness of ships and shipping. It is a dream come true for sailing enthusiasts, and a once-in-a-lifetime opportunity for anyone who is stirred by the sight of a square rigger under full sail.

Many nations maintain sailing ships in this machine age because they believe there is no better way to build character in young men than sail training. It encourages initiative, steadfastness, leadership and personal courage .... the records of the brotherhood of the sea sparkle with innumerable examples of the value of such training. The prestige of having served aboard a windjammer is no small matter.

To reach New York for the July 14 parade up the Hudson River, some of these tall ships will have sailed from their home ports as long ago as early March. Some will have raced from Plymouth, England, to Lisbon, Portugal, then 3000 miles across the Atlantic to Bermuda rendezvous, and a 630-mile northwest run, in company, to New York.

These ships are specifically built for training under sail. As these tall ships plough the oceans, the men who man this great fleet are helping to forge a bond of understanding and mutual respect around the world. As you visit the ships and talk with their officers, crews, and trainees, consider the thirteen participating nations, the thousands of people involved in such a gathering, the countless man hours spent in preparations which have resulted in this great spectacle OPERATION SAIL.

• July 12: Ships anchor in designated order in Gravesend Bay.
• July 13: 1430- Captains briefing aboard USCG 1730-2000: Reception at Chase Manhattan Bank.
• July 14: 1100- Ships will depart Gravesend Bay and pass official reviewing vessel, USS Randolph, and then proceed to anchorages below the George Washington Bridge.
• July 15: Ships move to assigned piers. 1400- Lifeboat races at U.S. Merchant Marine Academy, Kings Point. 1800- Commandant USCG reception.
• July 16: 1200- Ticker tape parade from Battery Park to City Hall. 1400-1800- Ships open to Public.2000-0100- Grand Ball, Holland America Line Pier 40, and seamen's Church Institute.
• July 17: 0900- Captains Symposium, Maritime Exchange. 1000-1800- Ships open to public. 1215- American Institute of Marine Underwriter's luncheon for Captains at India House.
• July 18: World's Fair Day, Singer Bowl. Public invited. 1000-1800 Ships open to Public.
• July 19: Divine Services Ships Depart.

(Taken from Operation sail guide book 1964.)

Celebration of the United States Bicentennial, the 200th anniversary of the adoption of the United States Declaration of Independence. Of the relatively few tall ships that were in service around the world at the time, 16 sailed to New York to participate in the Grand Parade of Sailing Ships. Each of the ships flew a banner featuring the tricolor star insignia of the Bicentennial. They are referred to in the official program book^[3] as the square-rigged school ships. In addition, there were 113 supporting vessels of the Op Sail Fleet listed in the program book.

Celebrating the Statue of Liberty centennial

Celebrating the 500th anniversary of Christopher Columbus' landing in America. Winner of the tall ships class was the Norwegian full-rigger Christian Radich.^[5][6] The fleet of thirty-four sailing vessels was led by the U.S. Coast Guard Barque Eagle, and included ships from Denmark, Argentina, Australia, Belgium, Bulgaria, England, Canada, Chile, Colombia, Germany, Italy, Israel, Japan, Norway, Oman, Panama, Poland, Portugal, Russia, Spain, Poland, Uruguay, and Venezuela. [author John Richard, Executive Director of Operation Sail 1992]

This ran from May 25 through July 31 with the traditional Parade of Ships in New York on July 4. Ports of call included San Juan, Puerto Rico; Miami, Florida; Norfolk, Virginia; Baltimore, Maryland; Philadelphia, Pennsylvania; New York City; New London, Connecticut; and Portland, Maine.

During the summer of 2012, Operation Sail commemorated the bicentennial of both the War of 1812 and the writing of "The Star-Spangled Banner," with ports of call in New Orleans, Louisiana; New York City, New York; Norfolk, Virginia; Baltimore, Maryland; Boston, Massachusetts; New London, Connecticut; Milwaukee, Wisconsin; Chicago, Illinois; Toledo, Ohio; Cleveland, Ohio; Detroit, Michigan; and Buffalo, New York.^[8] Tall ships representing nine nations, as well as many independently owned tall ships, participated in parades of sail in these ports, and were open for general public visiting at no cost.

In summer of 2026, in celebration of the 250th anniversary of the United States Declaration of Independence, visiting ships will make port calls in:^[9]

• Boston, Massachusetts
• New York City, New York
• Baltimore, Maryland
• Norfolk, Virginia
• New Orleans, Louisiana

Visiting ships will include:

• Cisne Branco (Brazil)
• Cuauhtémoc (Mexico)
• Gloria (Colombia)
• Guayas (Ecuador)
• Juan Sebastián de Elcano (Spain)
• Danmark (Denmark)
• Gorch Fock (Germany)
• Statsraad Lehmkuhl (Norway)
• Sagres (Portugal)
• Libertad (Argentina)
• Esmeralda (Chile)
• Amerigo Vespucci (Italy)