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Old 22-07-2014, 13:20   #1
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Inexperienced Couple Seeking Advice

Hello, my partner and I are inexperienced in sailing, but would like to find a way to reach Jamaica or Tortola. We were hoping that members of this forum could share their experiences with us, so that we may learn how to hitch-hike toward the Caribbean.

We are both college-educated individuals, male age 35 and female age 25, with a variety of skills to offer. Right now we are seeking a simple lifestyle, with purposeful work, and have been networking with organic farms through the WWOOF organization. We are willing to trade just about anything within good reason for an opportunity to sail to Jamaica or Tortola. What can we do to make our dream a reality?

Thanks for your insight!
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Old 22-07-2014, 14:08   #2
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Re: Inexperienced Couple Seeking Advice

There are some really cheap flights to Jamaica, but not Tortola. Also consider a cruise ship going to Jamaica or BVI and getting off the ship there. Sailing to either place from the USA is mostly to windward and will be a long and possibily uncomfortable trip, especially for non-sailors. It will probably wind up costing you more in the end, since you will most likely have to contribute at least food money for the boat.

Like they say, "nothing goes to windward like a 747".

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Old 23-07-2014, 05:59   #3
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Re: Inexperienced Couple Seeking Advice

where are you now? I can get you to key west from upstate New York area.


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