Sydney Flying Squadron

Sydney Flying Squadron is a long-established sailing club based in Kirribilli, NSW, that organises open-boat and skiff racing on Sydney Harbour (notably 18‑footer and 12‑footer events). The club website also references sailing courses and information for sailors, race results and calendars, plus on-site hospitality facilities (a restaurant and a café) and event/function hire.

The Sydney Flying Squadron runs no learn-to-sail school, no Tackers fleet and no formal syllabus — and it would argue it needs none. Its pathway into the sport is a standing invitation to step aboard a Historical 18-footer and learn by doing. Sailing experience is not essential, though the ability to swim is; newcomers are paired with an experienced hand who shows them what they need to know, and may sail three times before being asked to join.

The current crews span teenagers through to an octogenarian, which says everything about how accessible the club makes a boat type that looks terrifying from the shore. Those not yet ready to commit can first watch the racing from the spectator ferry that follows the fleet — a try-before-you-buy arrangement unique in Australian sailing.

Racing is run under the club's own handicap and point score systems, with scratch-start signal flags and staggered starts that are a living continuation of Foy's original innovation: the slower boats start first, the flyers chase, and if the handicapper has it right the fleet converges at the finish. It is a system that rewards crews of every standard and gives newcomers meaningful racing from their first afternoon. Volunteers fill the rest of the ecosystem — rescues, race control, the barbecue and raffles afterwards — and the club is explicit that this roster is part of membership, not an optional extra.

The honest footnote is that an 18-footer demands respect. Capsizes come perhaps once or twice a season, and a capsized 18 cannot be righted; the boat is towed to the closest beach, stripped of its rig and hauled home. New sailors learn quickly that these are unrestricted designs carrying bowsprits and spinnakers that dwarf an 18-foot hull, and that the thrill is precisely the point.

The clubhouse sits at 76 McDougall Street, Kirribilli, on the waterfront of Careening Cove at Milsons Point — one of the closest sailing addresses to the Sydney CBD, a short walk from Milsons Point station and the Kirribilli ferry wharves, in the shadow of the Harbour Bridge's northern approaches. The building operates as a genuine hospitality venue: Foys Kirribilli restaurant upstairs, the Flying Squadron Bar, and the Flying Bear Café trading seven mornings a week, all opening onto a waterfront deck, with the Heritage Room available for functions. It is an unusual arrangement that lets a small sailing club punch well above its financial weight.

From that base the Historical 18s race every Saturday through the summer months, the season running roughly from October until Easter, over traditional harbour courses with turning marks at places like Chowder Bay and Shark Island, as they have for generations. The racing water is the central harbour — deep, tide-swept and framed by headlands that bend and accelerate the summer sea breeze, with ferry lanes and weekend traffic adding a further layer of vigilance. For boats carrying such enormous sail plans on hulls under five and a half metres, those conditions produce sailing of genuine drama, which is exactly what the spectator ferry is there to witness.

The venue's harbour position also makes the club a natural host for the class's biggest occasion. Each Australia Day long weekend the Historical 18 Footers Australian Championship is sailed from Kirribilli, drawing the replica fleet — boats such as Yendys, Myra Too, Aberdare, Alruth, Australia IV, Britannia, The Mistake, Top Weight, Scot and Tangalooma — onto the same water where their 1900s namesakes raced before crowds in the thousands. Between the weekly racing, the championship and the waterfront hospitality, Careening Cove functions as both a working boatshed precinct and one of the harbour's most distinctive front-row seats.

In 1891 the Sydney draper and businessman Mark Foy called a meeting at Rainsford's Cambridge Club Hotel to found a new kind of sailing club. His Sydney Flying Squadron introduced sail emblems in bright colours, handicapping imposed at the start so that finishes were close, and a triangular course — ideas aimed squarely at spectacle. The yachting establishment recoiled, excluding Squadron boats from the 1892 National Regatta on the grounds that the emblems encouraged gambling; Foy simply financed his own rival regatta, open to all comers, with bands, chartered spectator steamers and a grandstand crowd on Clark Island.

The original club folded during Foy's overseas travels of 1892–93, but he revived it on his return, and the resuscitated club's first race, on 13 October 1894, went to the 18-footer Olinda.

Skiff racing quickly became a working-class institution: at the peak more than thirty 18-footers raced weekly, trailed by chartered ferries and illegal bookmakers. A 1935 breakaway formed today's Australian 18 Footers League, whose secretary James Joseph Giltinan launched the JJ Giltinan world championship, first sailed in 1938. Foy himself had taken his 22-footer Irex to England in 1898 as Australia's first entrant in an international sailing contest, and his interstate Mark Foy Challenge Cup of 1911–12 — decided by five seconds in Perth before an estimated crowd of 10,000 — is now recorded as the first Australian Championship.

He died in November 1950, the fleet flying black mourning ribbons; in October 2019 he entered the Australian Sailing Hall of Fame.

The modern club sails history rather than merely remembering it. The Australian Historical Sailing Skiff Association, established in 1990 by boatbuilder Robert Tearne and fellow enthusiasts, recreated the class as replicas spanning design eras from around 1900 to 1950, and that fleet now races weekly from Kirribilli. The Australia Day championship's trophies carry deep meaning: the Galloping Ghost Trophy, for authenticity, was cast from silver of the original Mark Foy Cup that melted in a 1958 fire, while the Raw Meat Trophy decides handicap honours.

Champions of the modern 18-footer scene — John Winning, Rob Brown, David Witt, Irishman Harold Cudmore — have all taken the helm in recent years.