We are not talking about a
circumnavigation here and this is a short term thing, so you could just buy any 35-ish feet boat (and there are thousands of them the owners would sell for cash now for 3/4 or less of the asking price) and go have a blast with it...then sell it for about the same
price or maybe a little less when you are done. Depending on your experience level and
budget, heck you could fly to Florida with 4 backpacks and a two weeks later be heading for the Carib. I would fight the urge to make this MORE about the boat than the adventure of where you want to go! It really all revolves around your experience level and
budget.
I just opened up a copy of Southwinds Magazine and found a
Pearson 365 Ketch listed for $35K. I bet $30 gets you the boat and you sell her for $25, try to charter a boat for $5 plus lets say another $5K in quick
gear upgrades....forget about it!
Ok too much
money, then the next page has a 30ft Bodga 1986 for $12K...you know $10K maybe even $8k gets the boat and gets you in the Carib out on the
water and
anchorages. Sell the boat for $5K when you are done.
Have more
money to spend....then hell, it'sa piece of cake to by a nice boat for $75K, sail and then resale for $60K.
We cruised with a
family of 4 on a
Pearson 365....space for a short term
cruise when you are living in the
water and out adventuring just isn't an issue, so my No 1
advice is go small, go easy and DO IT! Don't let people tell you that you are crazy, just go do it! I'm not kidding. Give me 4 plane tickets to Florida about a month before cruising season kicks off and I would have a boat and be at
anchor in the Carib before most of the "gotta have it all right and dialed in perfect crowd" even leaves the
dock for the first time after their 3yr
refit. Heck...that's sounds like a damn good reality show!
(Now if you don't have any experience in
buying a boat find someone to help you, even if you pay them $500 to help you find it and look at it. Their experienced eye can make this approach really
work. But if you know NADA about boats, boat systems and
buying boat, then trying to do something like this on your own could be a Capt Ron Disaster where you never leave the dock)