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Originally Posted by LeoneLover13 
How do you know if you are ready to make the move? Or even if you are suited to it?..... Did you just jump on the boat and were fine, were you nervous before? I would really appreciate some stories on how the process went for everyone.
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Our family has been saving and planning for 5 years but we'd only sailed before kids, not with them. We decided to charter for a week between Christmas and New Years to test things out. We needed to see if anyone got violently seasick, or felt too much cabin fever, or if taking care of the kids and the boat were simply too much, or if we still liked sailing after all of these years, and what the kids felt like when they came into a new harbor and met people.....and more of course. We found we had some difficult relationship things we have to work out. I, for example, always question things, and want to know every detail of every plan before it is executed, but my husband is more likely to somehow secretly gather all of the information from the chart/cruising guide/gps and just pull into a harbor find the mooring ball (or slip or anchorage), pull right up to it, stop the boat perfectly, and tie up all single handed while I'm trying to work out the perfect plan. Clearly letting other people take charge is something I need to work on! My dd, 5.5, got her sea legs instantly but didn't become any less defiant on the boat which could have caused her physical harm if we hadn't forced non-negotiation when we told her to do something or sit somewhere. That was very different than at home where we work things out very slowly with her to get her to go along with a plan. Sometimes on a boat you just don't have that time, i.e. she couldn't sit on the bow when we had to tack the jib. My ds , 2, bumped his head a LOT for the first couple of days but figured his way around the boat pretty darn well after that, and he's actually way more sure footed on land since! He's easy going and was completely fine tagging along with our plan. He did however disable the electronics, turn off the refrigerator, waste plenty of water, take apart 6 flash lights at once, blow the air horn, and remove the covers from the engine room. Trouble, that one, but at least he'll be able to fix everything on a boat before his 5th birthday. We found that even though we had a couple of difficult interactions we're still on.
I find myself second guessing at home sometimes, surrounded by my awesome espresso machine, hot showers, and excellent grocery stores. I also feel like I need to run all of the what-ifs by my husband. But when I talk to my friends, and think about boats, and read cruiser blogs, and look at pictures of our recent and past sailing, and tell people that our family is going sailing into the unknown, I'm thrilled, and happy, and feel like I'm sure of my path. My mom looked at our recent sailing pictures and mentioned that I look the happiest I've been in years. A friend on Sunday was asking questions about or trip and stopped me to say she'd never seen such a spark in my eye. I imagine my family out there in the world in October 2012 and know that our home will be wherever we drop the anchor.
So, being that sure, we're putting another offer on another boat. Hopefully this one will accept and we'll be sailing every weekend this summer and thinking about how to sell all of our possessions in the next year or so. Can I bring my 8 quart La Crueset dutch oven with me, it could double as an emergency anchor, right?
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