Prior to my first trip south to check out the boat, I attended the Great Loop Cruisers Association's Fall Rendezvous at Joe Wheeler State Park in Alabama. By the time I registered, there were no rooms left at the park so I found a B&B nearby, the name of which is Longing for Home. This B&B turned out to be the destination of choice for a night out for the Loopers from the Rendezvous. So I not only got to learn from the daytime seminars and lectures but informally in the evening's chats at the B&B. Longing for Home was a great place to stay and the Rendezvous was very informative.
I would recommend going to a Looper Rendezvous, at least one, and then if you are on the water and can manage to co-ordinate and attend others, that would be nice. I don't think I would drive too far by car to keep going to 'em. They are informative, however anyone that is planning a trip of this nature had better be doing some deeper investigation into all the "ins and outs". And the prep, reading and shopping, are in fact part of the fun of it. At least at this juncture of my preparation, this seems to be the case.
In my time I have outfitted camper boxes, back country trips, campers, motor homes and a couple of temporary residences. Here is what I've found: you can spend a fortune, in fact let me re-phrase that, it will cost a fortune, but it doesn't have to be the "King's Ransom" kind of fortune.

My philosophy is: "you own it all"! That's right, and now I'll return to my own set of circumstances to complete my example, an example that would not hold one iota of merit in the eyes of my wife, "Shopping Marci". In her eyes, if it ain't new, it don't count... end of conversation! Thank goodness, I get first right of attack, so to speak. And only because the boat has to be moved from Florida to Tennessee (in the winter). So by the time she gets a shot at it, I will have been using it for some weeks. Now she will still go shopping once the boat is back home, and the truth be known, she already has done a little, but the financial damage won't be as bad as it might have been.
But back to my outfitting philosophy. When you get to figuring all you'll need, from pots and pans to dish towels, it starts to add up quickly. However you probably have duplicates all around the house, in the camping gear and at that summer place. As you talk about it to friends and family, you might even find out they've got duplicates of the "junk" that is needed. This includes tools, rope, electrical extension cords and the list goes on.
By the time my crew and I were ready to go to the boat for the first time, we had an F-350 flat bed loaded down. And once we got to Florida and found that some of the stuff simply didn't work or wasn't needed, we hit the Good Will store with donations. They have 'em everywhere.

My first crew consisted of my kids: From left to right Jeff, Elizabeth and Ronnie.These guys were great! They hauled, cleaned, fixed and, most importantly, put up with me. I can be a little overbearing during what I consider a "big deal" and the new boat qualified as a big deal for me.
Well, after all the cleaning, organizing and generally having a really fine time, we actually got to go out to sea on the boat. The highlight of the trip for all of us. It turns out that our very capable boat mechanic, Gary, is also a Captain and had done this type of work in the islands for several years. We got to call for a draw bridge to open for us and to see a really cool lighthouse as we went out for an ocean cruise. Nice point to make reference to when you want to get the boat back where it belongs for the night. The seas were running about two feet (I love this nautical talk) so we got bounced around a little. I have been to sea however the kids never had and I was watching for any greenness around the gills. Everyone did really well for our first shake down cruise.
I had started the list while driving back from the Rendezvous at Joe Wheeler. I began writing things down on a steno pad and by the time I had arrived home, I had a five page list. It was a good time to work on it as I was alone, had no interruptions to speak of, and was fresh from the meeting with all kinds of ideas.
I'm sure that "Shopping Marci" will fine tune what I have done, but the damages ($$$) won't be nearly as bad.
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