Shanachie, Bristol 30
Join Date: Jan 2014
Location: St. Petersburg, Fl.
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Re: 25-27 foot sailboat to sail Bahamas, possibly Cuba
I'd look at a well-kept Bristol 27 or 30, with an inboard diesel, which usually can be had for a couple thousand more than your current price range.
Sailing through the islands on a 5,000-pound, outboard-powered sailboat can be done, but it would be a wild ride in the winter "Christmas winds" and the 6- to 8-foot seas that accompany them in many places.
You would also find crossing the Gulfstream challenging, although possible, with slow progress and the prop coming out of the water with each wave.
The big issue is not the initial cost, but what shape the boat is in and how well-equipped it is.
You might feel good "saving" a couple of grand with a $4,000 purchase price, but that glow will disappear when you spend thousands on an autopilot, new rigging, acceptable sails, needed repairs, etc. Very few of these bargain boats are in any condition for a trip.
I've owned a C&C 25 and a Bristol 30 in recent years and sailed them around South and western Florida. I could get beaten up pretty well on the 25 when conditions worsened. The Bristol, hardly at all. There's a big difference in the designs.