The Sinclair family have a long association with Whakaraupō Lyttelton Harbour, with the Scotsman William Sinclair being one of the port’s earliest boatbuilders. Arriving in 1863 from the Ballarat goldfields in Victoria, Australia, William had set up his shipwright business by 1870 in Dampier Bay near the dry dock. His Australian-born son Jimmy carried on the business, and both father and son were famous for their love of yacht building and racing, with their yacht Little Wonder successfully competing in the annual Lyttelton New Year’s Day Regatta against their arch rival, the Miller’s Pastime, through the 1880s. Jimmy Sinclair continued to modify Little Wonder to meet the Pastime challenge, but after Little Wonder’s 50 minute loss to Pastime in the 1890 Regatta, he decided it was time to build a new yacht to reclaim the title of Champion Yacht of Lyttelton.
That yacht was the Mascotte (named after the comic opera Mascotte), and she was 16 m long with a 2.7 m beam and 2.4 m draught. Gaff rigged with a 12 m mast she carried 300 square metres of sail and 14 tons of ballast including a 7 ton lead keel. Laid down in April of 1890 she was launched from the Lyttelton slip near the dry dock by Miss Barbara Sinclair just in time to soundly defeat Pastime at that year’s Akaroa Regatta on 16 December. Mascotte went on to dominate the waters of Lyttelton from 1891 on, and was also named New Zealand Champion at Wellington in 1892, holding the Championship title for another four years.
Jimmy Sinclair's passion for yacht racing and innovation didn't end there, and in December 1895, he launched Bettina (named after the heroine in the Mascotte opera), a yacht that broke the mould with its radical lateen sail design and excellent performance in her class at the 1895 Akaroa Regatta. The Christchurch Press declared her an "exceptionally smart little yacht" with its sail suspended between a ‘hairpin’ or bipod mast in place of a conventional mast. The design, for which Jimmy had taken out “letters patent”, was based on an ancient rig first used by Nile reed boats. In the 1896 Lyttelton Regatta, beset by gales, the light centreboarder performed so well that Jimmy and his 12 year old son Jimmy Jr. easily won a handsome victory in their class. By the late 1890s Mascotte was beginning to show signs of deterioration in her hull due to the constant stresses incurred in racing and modifying such a large yacht. Bettina on the other hand, continued racing with much success, taking handicap honours in the 1900 Lyttelton New Year’s Day Regatta.
This competitive yachting tradition carried on through to the next generations of Sinclairs with the founding of the Canterbury Yacht and Motor Boat Club in 1921. Of the Club’s 40 founding members, seven were Sinclairs! It’s even said the CYMBC was founded to enable Sam Sinclair to sail the Linnet under the Club’s flag for Canterbury in the 1922 Sanders Memorial Cup in Dunedin. Sam Sinclair’s nephew Eliot, true to his family’s tradition, was also an accomplished yachtsman who notably went on to win five consecutive Sanders Cups for the Club and Canterbury from 1932 to 1936. In the 1936 Sanders Cup race at Auckland, Eliot’s Avenger of Canterbury overcame the trials’ favourite Aileen with Troy Willetts at the tiller. Then over a decade and a half later, in November 1953, this unrivalled veteran yachtsman again won the privilege to defend the Sanders Cup for Canterbury, sailing Genie in the trials off Lyttelton, and was runner-up in the hotly contested Sanders Cup of January 1954, won by Otago’s If.
In 2001 the CYMBC amalgamated with the Banks Peninsula Cruising Club to form the Naval Point Club Lyttelton, and in 2021 the club commemorated the centenary of the founding of the CYMBC, and 150 years of the Sinclair’s sailing tradition in Whakaraupō Lyttelton Harbour. From William and James, to Sam and Eliot, the Sinclair family's legacy in the world of yacht racing continues to be celebrated to this day.