All are members of the Diocese of West Yorkshire and Dales Motorcycle Club, formed for clergy and lay motorcyclists.
Ten bikes will start the trip on Monday from Leyburn in North Yorkshire.
Reverend Michael Hepper from St Matthew's in Leyburn said it would be a "very different kind of retreat".
The 725-mile round trip will begin with a 200-mile ride to Barnard Castle, over the moors to Hexham and through the Kielder Forest to Jedburgh and Edinburgh.
The riders will continue to Fionnphort on the west coast of Scotland via the Trossachs and the Isle of Mull.
The "pilgrimage" ends on the island of Iona, known as "the cradle of Christianity" because St Columba is said to have landed there by coracle from Ireland in AD563, bringing the Gospel.
Mr Hepper said the trip would be "a spiritual experience and an adventure".
Reverend Neal Lefroy-Owen, of St Hilda's, Halifax and St John's, Warley, said: "It's great to be able to share my love of riding with fellow Christians from the new diocese and to get to know them better."
Reverend Canon Stephen Kelly - area dean of Wakefield and priest in charge of Woolley and West Bretton, Reverend Canon Paul Tudge of Farsley near Pudsey, and Reverend Vic Iwanuschak, Incumbent of All Saints Pontefract will also take part in the pilgrimage ride.
Five lay riders and four pillion passengers will accompany them.
Five Yorkshire vicars are preparing for a five-day motorbike "pilgrimage" from Yorkshire to Iona off the west coast of Scotland.