The event was organised for the first time in 1975 to celebrate the 700th anniversary of Amsterdam, under the name 'Sail Amsterdam 700'. This led to the establishment of the Stichting Sail Amsterdam.
1975 edition
The tjalkStockpaerdt participated in the event on inception.
2005 edition
SAIL Amsterdam 2005 was held from 17 to 22 August, the 7th edition of the festival. The event was expected to attract 2 to 3 million visitors. The official number of tall ships which participated was 21 but in total over 50 ships with at least 3 masts were present. There were also several ship replicas, hundreds of classical sail- and steamships and some modern marine ships. For the first time several modern yachts and a submarine were present. The tall ships were moored in the IJhaven and in Amsterdam North and the Varend Erfgoed boats were moored in the nearby, where one can also find the Nederlands Scheepvaartmuseum with its replica of a Dutch East India Company ship, which is permanently moored there. The main ships, in the order of the official walking-route were :
STS Sedov
Tenacious
Amerigo Vespucci
Mir
Kruzenshtern
Prins Willem
Stad Amsterdam
Sørlandet
Europa
Oosterschelde
Eendracht
Sagres
Swan fan Makkum
Alexander von Humboldt
Khersones
Pogoria
Shabab Oman
Dar Młodzieży
Statsraad Lehmkuhl
Mircea
Dewaruci
Tarangini
Kaliakra
Smaller events included an exposition of yacht building and a parade of carnavalesque floating creations. The event cost around €7.5 million to stage which was financed by sponsorship and trading activity. On the first day, the ships gather in the locks at IJmuiden for the Sail In or Parade of Sail through the North Sea Canal to Amsterdam, led by the event's flagship. In 2005 that was the Stad Amsterdam, which was supposed to reach Amsterdam first, but she ran aground with the Dutch crown princeWillem Alexander aboard and the Statsraad Lehmkuhl then preceded her.
SAIL Amsterdam 2015 was held from 19 August to 23 August 2015.
List of sailing ships participating in Sail Amsterdam 2015
2020 edition
SAIL Amsterdam was scheduled to be he held from 12 August to 16 August 2020, but has been cancelled after the Dutch government banned organized events until 1 September 2020 due to the COVID-19 pandemic. The organization decided it was unrealistic to postpone the event, as it was impossible to say if such a mass event could be organised safely in 2021.
2025 edition
SAIL Amsterdam 2025 will be the tenth edition of SAIL Amsterdam, and the first one since 2015 as the 2020 edition was cancelled. It will be one of the main events in celebrations to mark 750 years of the city of Amsterdam. It will also be 50 years since the first edition of SAIL Amsterdam was held.