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Jeanneau 57
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Unfortunately the rules have changed and every non-American and non-LPR holder must have a valid visa when arriving in the USA via boat. This also applies to citizens of those nations who can fly into the USA using ESTA and the visa waiver scheme.

Since the US Virgin Islands are only a $30 ferry trip from the BVI, one workaround is to sail to the BVI and then enter the USA via ferry. Once the person has been allowed into the USA (usually for a 3-month period of stay), they can then leave and return via boat.

Last time I was clearing into St. John in the USVI I was talking with the immigration officer who told the story of people still sailing to the USVI without a visa and that usually they will let them return without problems, but if they are cantankerous then they follow the official procedure and force them to leave BUT also put a mark in their immigration records that will prevent them from entering the USA for 5 years. So while I know how difficult it can be for a Filipino to get a tourist visa I would recommend having them go through the procedure; perhaps paperwork regarding the method of travel (sailboat to the USA) would make it go smoother.
 

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Jeanneau 57
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It is mandatory he needs a B1b2 visa.
The work around Zanshin mentions does not work anymore.
Mark
Mark, are you certain about that? I asked at immigration in St. John last year and they said that it is a valid method. I wouldn't be surprised if they changed policy, but it would have to be a recent change. It wouldn't make much of a difference, since the foreign crewmember could just remain in St. John and wait for the boat, crewed only by U.S. nationals or permanent residents, to clear in by themselves before rejoining the boat.
 
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