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Old 04-04-2015, 18:35   #31
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Join Date: Aug 2012
Location: Cruising the Gulf of Mexico.
Boat: 1980 Morgan 415
Posts: 1,452
Re: Questions about a prolonged trip in the Caribbean

$20k can buy a lot of boat if you shop around.

A couple of points on single handing. Reef before you need rest and heave-to when you are exhausted.

Looking for another pretty place to work on the boat.

Working on spending my children's inheritance.
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Old 08-04-2015, 11:29   #32
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Join Date: Mar 2011
Location: nj
Boat: Endeavour E 43
Posts: 80
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Re: Questions about a prolonged trip in the Caribbean

Best is to sail with others a few times, get to know the area and the boats, you cannot possible get the answers from just reading, although many members here have great tips and advice.
I can tell you more about sailing opportunities if you give me your email address and I will mail you directly.

Here a few isolated tips:
  • Much space on a boat is more needed for accumulated junk and stuff than for living. You will find out.
  • Get a wide body roomy boat and a larger boat. You can get great buys if you look around long enough. Buy only from an owner that took great care of the boat, perhaps got too old. Beamy may be slower, but you don't need racing speed. Don't buy a new boat
  • I have met young solo sailors on 25 to 30 ft boats, but if you sail with friends and family, you need more space.
  • The areas are quite different: Bahamas are shallow. You need a long full keel and a draft of 4 feet, including Cuba. The other islands have mostly deep water to the shores. You can handle a 7 ft draft. But you need a 150 foot anchor change (plus spare) and a good windlass.
  • Biggest problem in any islands are repairs and dependable service, including caretaking if you fly home and leave the boat. It pays to get good gear, very well installed before you leave, spend at least 6 months on that and on trials, check everything. Mostly all electric and electronic wiring, switches, fuses, lights, generator, and all equipment. Most important is autopilot for solo sailing and self steering gear, wind generator, stove and propane system.
  • There are many helpful sailors out there (and some really know their stuff), use all the communities and VHF nets.
  • You have enough money and credit cards? If not, can you earn some on the way? Are you an electronics engineer or an electrician? Would you buy a decent boat and charter? Are you a master chef? Just don't smuggle.
  • I have sailed small boats and race boats in Europe, a Morgan Out Island (very beamy and shallow) in the Bahamas for 20 years, and presently have a great US-made Endeavour Ketch 43, kind of hard to get, the Endeavour 32 is much praised, not the 42. I have sailed various Benetau, Catalinas, and others, cant' say I like these modern lighter boats. Catamarans offer more space, but the popular ones are too low and get hit by waves at the bottom. Docking is more expensive, many are cheaply made, not good for tacking, a bit more expensive than mono hulls, not for you. I suggest any old heavy boat and get yourself a new engine, small generator, autopilot, and decent electronics. Good sails in Hong Kong.
  • Get good guide books: Late Harry Kline's Bahama Guide is still the best. Chris Doyle's Guides for Virgin Islands to Eastern Caribbean, A gentleman's guide to sailing south by Bruce van-Sant. The guys at Bluewater Books in Fort Lauderdale are the best in consulting on charts and books, even though I have bought and sold and traded most with other cruisers. (You can buy just about anything from other sailors).
  • That's it for today, good winds to you and others who cannot be convinced to stay on land.

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Old 08-04-2015, 12:49   #33
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Join Date: Oct 2010
Location: Oregon
Boat: 57' Laurent Giles Yawl
Posts: 755
Re: Questions about a prolonged trip in the Caribbean

You may like Buy, Outfit, and Sail by Fatty Goodlander. We harbor hopped around Africa the same time he did, and he's, like, the real deal for going far, safely, on a budget.

There Be No Dragons by Reese Palley is in a similar vein.

I recommend these books because that are about focusing on what is important. I've met a few folks who bought sturdy and minimally equipped boats for <$10k, and went on to have a blast with them. So I feel $20k is doable, but you have to keep your whits about you and make good choices and have focus on what is important.

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Caribbean, rib

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