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Re: Hello from Canada. Looking to plan a long trip, any help would be appreciated.
Lots of fantastic experience and knowledge on these forums; as you browse through the various topics you might start to build a picture of how you could proceed. Reading everything from Joshua Slocum to "Heavy Weather Sailing" to the "Annapolis Book of Seamanship" will either hook you or scare the &@&$ out of you....
Most importantly, GO SAILING.
Join a dinghy club or as take out a crew or social member at a yacht club. Search out "crew wanted" listings for club race nights. Take a sailing course or two...
Before you know it, your new sailing connections may start asking you join them as stand-in crew, or for day sailing excursions. Being willing to help out on boat repair projects and on launch day can earn you some major brownie points with many skippers; but even more important is enthusiasm and an openness to watch, listen and learn.
Funny, most Sailors love being around other people who are enthusiastic about sailing. With recreational sailing, skippers often see this as a more valuable attribute than sheer knowledge and experience.
If you love it, and make it part of your life experience, there is no End Goal...there is always more to learn and experience. Maybe one other suggestion as you look for various sailing mentors; be a little skeptical of those who might sound like they know it all, or have done it all. That goes double for situations where safety is a priority issue, eg. long-distance cruising or racing where mother nature (or Murphy's law) may hold more cards.
Great Lakes, Canada