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Boating around the Caribbean

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On the Jeeebus wishlist - which Mrs. Jeeebus has not said no to yet - is the 38' Boston Whaler Outrage:

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I wouldn't take it hundreds of miles away to the Virgin Islands, French Caribbean, etc., but we've been looking at buying a place on Bimini (50 miles), Grand Bahama (60ish miles), or Abaco (100 miles) and the crossing is very comfortable on a boat like this. That said, weather and waves are always the key factor even on a 40'+ boat. It could be flat off the coast here and once in the gulfstream you're looking at 10'+ waves. That's not fun on any boat.

those engines are almost 30K each.
 
do a search for doing the loop . All protected waterways , intracostal canals . In the open ocean , 20~30+ ' waves could turn your world upside down .
The Lake Michigan portion can be sometimes problematic for small craft (and even larger craft). Typically waves are 1-8 feet, but, 20-30 foot waves are sometimes recorded during storms. It is thought that a 40+ foot wave sank the Edmund Fitzgerald.

(note: As Herm0016 pointed out, the Fitz was Superior, biggest measured on Lake Michigan top out around 30 feet, but, as mentioned earlier, typically they are under 8 feet other than storms.)
 
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The Fitz Sank in Superior, which has worse weather than Michigan.

Lake michigan is generally a little choppy, but not bad, and there are a lot of ports to duck into if needed.
 
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