Old as Dirt!
Join Date: Nov 2008
Location: Tampa Bay Area
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For the trip you describe and the size of your family, you might find that a Gemini 105 Catameran would be just the ticket. A cat is somewhat easier to adjust to for non-sailing wives and the boats are pretty easy to handle with a bit of training. Moreover, they are good coastal cruisers and could easily take you from Maine to the far Bahamas in reasonable comfort. The boats are also relatively simple making fixes less problematic; and one in reasonably good condition can be had for well under $200,000.
The nice thing about coastal cruising in the US is the common language, the largely friendly natives and a super abundance of interesting places to visit. Note, however, that there can be challanging conditions even along a friendly coast so the initial learning curve will be steep.
Do it while the kids are young. They can be home schooled without too much difficulty for a year and, by using events on the boat, they will learn as much history, geography, math and science as they might in a classroom, if not more.
"It is not so much for its beauty that the sea makes a claim upon men's hearts, as for that subtle something, that quality of air, that emanation from the waves, that so wonderfully renews a weary spirit."