Toby was born to a dinghy racing family and was surrounded by sailing more-or-less from birth. He received his first boat – a bright red Optimist dinghy – for his fourth birthday and has been out on the water as often as possible from then on. He has won World and National titles and captained his University sailing team. It was during his time at university he discovered keelboat racing and continues to sail big and small boats to this day.
After leaving university in 2005 he got a job writing for an online sailing publication and has continued writing for both cruising and racing publications ever since, covering two Olympic Games and other events across the globe.