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We (British citizens,Brit boat) visited the US in 2012. We had to apply for B2 visitor visas which you must get in advance of arrival - we got ours in Barbados at the US embassy because its the application centre for non-Caribbean residents within the Caribbean. You may wish to do it in your home country before departure. You have to do the online applicaton process and book an interview - it may take a couple of weeks. The B2 is valid for 10 years and multiple entries but you only get 6 months per entry. You can leave the US and come back - usually via Canada, Mexico or Bahamas - for a renewal, but if it looks like an 'overnighter' device then you may be challenged on re-entry which would be very problematic; most people we spoke to planned to spend at least 2 weeks out of the country. Hearesay is that the Canada route is more friendly in this regard. I'd not recommend using Cuba as its technically illegal to sail from America to Cuba even as a non-US national.
We needed more than 6 months in one entry to allow us to complete our east coast trip. You can apply for a 3 month extension once you are in the country - I wouldn't recommend asking for it when you first rock up. There is an online application process and fee to be paid. It can take up to 3 months so do it fairly early on. If your extension has not arrived by the time your 6 months is up you are in limbo as far as CBP and immigration are concerned and you could be asked to leave although this would be harsh as they can see your application. We stayed 7 months in total and our extension arrived before the day we sailed - to Cuba!
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