I agree with Bill Trayfors' reassessment that with your experience you can probably do it. And that you should take your time. I made essentially the same trip and for a variety of reasons hurried it too much and now regret that I didn't spend more time. I also didn't have enough experience when I started so ended up paying a delivery captain
to sail with me for the first part of the journey. It's one way to learn but can have its own problems.
I know little about the details of trawlers but my experience on that trip is that you are heading against currents and wind for the majority of it. So, if people think that cruising speed is 6 kt then you'd better count on less than 5 because you'll face a 1 kt or more current against you for the majority of the time once you turn east at the TCI. And, even at 10 kt I don't think you can hop from marina to marina. From Provo (TCI) you'd have to go to Monte Cristi, DR and that's over 110 nautical miles. You wouldn't want to come into any port, once you leave Florida, in the dark. That means an overnight crossing. That trip is outstanding but... You have to cross the Caicos banks and you must do that in daylight or seriously risk hitting a coral head
. And you wouldn't want to think about making land in the DR until 6 or 7 AM. Then from Monte Cristi to Sea World. Then I don't think there is another real marina (going east) until you get to Ponce, PR. My suggestion: learn to anchor
, get a good dinghy
, plan on lots of nice stops in kind of remote
places along the way, plan on at least 2 months and enjoy yourself. It's a real slog of a trip once you turn east!!
I also question whether you can spend $40K on a boat and make that trip. I've been watching a friend in our marina in PR working on someone's boat and as soon as he fixes one thing he finds another that really needs repair. You are likely to find that you need $20K to get things in shape and to set things up to your liking. Once you get to the Virgins you may have more time but the price
and availability of parts
is going to be a lot worse than in Florida. Tortola is a center of sailing and I'm sure that you will be able to find parts
and mechanics, welders, etc. But it won't be cheap! For example, you could easily spend $10K on electronics
if you want any integration of GPS
, chart plotter and depth
gauge. And a short wave radio
is almost certainly wanted for weather and safety
, that's probably $2K right there.
I admit that I made essentially the same trip without the needed experience and that I was never in serious danger
. So, I think that you can do it. And I think you will probably not regret the experience but keep asking questions and pay attention to folks here because there is a lot of experience.