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Arriving to Caribbean with a sailboat/try to get to mainland

by MarkusUz Online Now Jan 25, 2013 at 1:41 AM

Hello! I am trying to do a around-the-world trip without using any airplanes. I have a Finnish passport. Currently I am trying to find a boat from South Africa to the Americas. My most probable destinations would be the Bahamas or Tortola (British Virgin Islands). And from either of those I would need to get to the mainland to continue my travels. (Those islands seem to be the destinations where the boats go..)
Now, I think the Bahamas would be my first choice because I could get the ferry to Florida. I have asked around and I think if I purchase an open ticket to the ferry the Bahaman authorities shouldn't have a problem. To pacify the US immigrant I was thinking that I will buy a plane ticket from USA to my home country of Finland. And then just cancel the ticket if I choose to continue my trip. I would then go cross the border to Mexico. Do you see any problem with this plan?
Tortola is a bit trickier. There is a ferry to US Virgin Islands and from there to Puerto Rico and from there to Dominican Republic. But from there I would need to find a sailboat to Florida or Mexico. Cuba would get me nearer also. But the sailboat I couldn't arrange before visiting the yacht clubs etc. So it would be quite complicated if the immigrant authorities would always be asking for prove to leave country etc. How do you see it going?
I appreciate any help or advice!
Thank you!

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