Kent Police said the men were organised, professional thieves who stole lorries and goods to sell on.
One refrigerated trailer contained £201,000 worth of Toblerone, which has never been recovered.
Whisky with a retail price of £23,000 was stolen from the trailer of another lorry parked in a haulage yard.
Maidstone Crown Court was told the thefts, involving three lorries, took place in April 2013.
Police said the theft of the whisky from a yard in Lydden was discovered when the lorry driver arrived at the Port of Dover en route to the Continent.
A second lorry, worth £40,000, was taken from a haulage yard in Whitfield and discovered four days later with false number plates in Eythorne.
The third lorry, which contained the chocolate, was stolen from the haulage yard in Lydden and later found abandoned in Tarleton, Lancashire.
The men were arrested after police searched properties in Kent, Merseyside, Lancashire and North Wales.
Lee Gilmore, 33, of Sidney Powell Avenue, Liverpool, was jailed for four years and eight months, Jeffrey Hamid, 31 of Hargate Road, Liverpool, for four years and six months and John Dahl, 44, of Aysgarth Avenue, Liverpool to four years and eight months.
Darren Price, 39, previously of County Road, Liverpool was sentenced to four years, eight months, Stuart Nicolson, 48, of Bindon Blood Road, Whitfield, Kent to four years and Graham Ascroft, 55, of Higher Lane, Tarleton, Lancashire, to four years eight months.
Six men have been jailed after lorries and their loads, including whisky and chocolate, were stolen in Kent.