Join Date: Aug 2006
Location: Arlington, VA
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In your stead, I'd choose the British Virgin Islands as my base. It's "non-US" alright...there's plenty of difference between the BVI and the adjacent US Virgin Islands. However, the USVI are close, as are the Spanish Virgins (East of Puerto Rico).
There are lots of used boats for sale in the BVI. As a first contact, I'd talk to Chris or Karen at BVI Yacht Sales. They're knowledgeable, straightforward, and helpful folks.
Cruising with an infant can be a challenge, but not an insurmountable one. I'd want a place with some medical care (the BVI), backed up by higher-level medical care (USVI and, especially, Puerto Rico) not far away.
Sailing in the BVI is fun, and you can get all the ocean sailing/bashing you want nearby. Or, you can just enjoy island hopping...there are lots to choose from.
While the culture is "foreign", it's not THAT foreign. They speak English, American dollars are the currency, buoyage is U.S. (red right returning), and there are lots of both American and foreign visitors and residents. A really good place to cut your teeth in cruising and in "foreign cultures".
And, just to the East across the Anegada Passage, the Leewards begin, arcing southeast to the Windwards, Venezuela, etc.