Expedition Navigation Software 
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Beginner question - what series of settings do i need to enable for expedition to optimise a route where the line between two marks might hit the tip of an island or peninsula, for example? Can I set expedition to automatically route around land and observe navigational marks and buoys, for example, or would I need to set each one along the course as a mark and then tell the software how to handle each mark (leave to port vs starboard, for example). Thanks!
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Fewer marks are always better.
Use the avoid land function to avoid land. If there is anything specific (traffic zone etc), you can also use a race note.
If you haven't seen them, Will Oxley's ebooks are teh best place to start. They contain a lot of hard-earned knowledge.
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Thank you - I read Will's introduction book and found it very helpful. I added some race notes to block off some of the tips of the land along the way and that might have helped.