Maybe has a rather famous history, built in 1929 for Jan Jacob Van Rietschoten, father of The Flying Dutchman, Cornelis 'Conny' Van Rietschoten, the only skipper to win the Whitbread Round the World Race twice. In the hands of the Rietschoten family, Tall Ship Maybe spent many years sailing around the world. Jan Jacob Van Rietschoten wanted a strong sea worthy vessel, so had Maybe built with extra strength by using steel frames, a hardwood hull and teak decking.

During the Second World War ‘Maybe’ was taken to the Dutch town of Jut where she was hidden in the mud in a remote backwater. After the war ‘Maybe’ was completely restored at the same boat yard where she had originally been built but with a new rig replacing the original gaff rig.
A major milestone in Maybe’s history is that she took part in the first ever Tall Ships Race in 1956. She is now one of the few boats that took part in that first race to still be competing in the International Tall Ship Races. A real claim to fame! Tall Ship Maybe returned to the Tall Ships Races in 2009 and has taken part in the Tall Ship Races and Regattas every year since. In 2017, Tall Ship Maybe will be taking part in the Transatlantic Tall Ship Regatta visiting Greenwich, Sines, Bermuda, Boston, Quebec and Le Havre.
In 1962 Tall Ship Maybe was bought by the Swiss family of Hans Fehr, who were experienced sailors and enjoyed sailing in warmer climates. She sailed mainly around the Mediterranean and in the 1970’s regularly crossed the Atlantic between the West Indies and the Mediterranean. In the 1980’s she also sailed through the Panama Canal and up the east coast of the USA to Canada.

Tall Ship Maybe was sold to her present owners in 1989 and underwent another complete restoration returning to sailing in 2007. She returned to the Tall Ships Races in the Baltic's in 2009 and successfully completed a full season of Tall Ships Races and Regatta’s in 2010.

In 2011, Tall Ship Maybe was restored to her original gaff rig.