We spent a week cruising the Grenadines and later entered the Tobago Cays from the southern entrance, a pass that today the bareboat charter managers and guide authors claim is too difficult to use. We found that if there is good light and the skipper reads carefully the sailing instructions on the back of Imray Iolaire chart B31 or B311, or the piloting directions found in Street’s Cruising Guide to the Eastern Caribbean: Martinique to Trinidad, and uses eyeball navigation with a crewmember on the foredeck or up the mast, the southern entrance is not that difficult.
Eyeball navigation is much better from the bow than from the cockpit, and standing on top of the bow pulpit is better still than standing on deck. If it is a tight situation or the light is fading, a crewmember piloting from the lower spreaders makes everything clear. In my early days of chartering and exploring the eastern Caribbean, often without the aid of a detailed chart, one of my crew or I would spend a lot of time conning Iolaire from a perch up the mast.
Before the late 1970s, when Imray Iolaire charts became available in the marine hardware stores throughout the eastern Caribbean, obtaining charts in the islands was extremely difficult. We ordered ours from the United States or England, and it often took six weeks for them to arrive.