I began my persistence for learning sailing in the summer of 2011. Prior I had only sailed on a cruise ship and 43 foot sloop boat. Those trips conveyed openings to explore destinations off shore. The cruise ship was a typical scheduled stops format, with everything you need away from home. It was enjoyable and sparked interest in traveling outside the USA, via water. Later the same year, I embarked on the Black Boaters Summit (BBS) 2009. This 10 day adventure acclimated me to real adventure traveling. It is significantly different than a road trip or cruise ship.
Sailing can be a peaceful self exile from most technology and civilization. Cell phones will work eventually, and a ship's radio to call land or other ships is on board. Many ports and harbors offer WiFi, sometimes free or at a cost. A few skills are helpful while sailing, swimming, CPR and First Aid, ropes and knots. I was already a certified CPR and First Aid instructor. I took swimming at a YMCA, in 2010. My profession of emergency services had plenty of training on ropes an knots. It would be the summer of 2011, when I could attend a formal sailing course.
In that summer, I spend two weeks sailing in the Caribbean. A week in the north sailing with SailFETE around Abaco, Bahamas and a week in the east, around the British Virgin Islands with the BBS. On both trips, the captain of the ship was kind enough to teach me some basics of sailing. I had also learned a few things on the 2009 sailing trip. I recall doing a lot of different tasks, however I didn't understand the full tactics and planning necessary for the whole trip. This would come after having a formal education of sailing.