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Old 03-21-2008, 02:55 AM   #1
Join Date: Mar 2008
Posts: 7

So I'm going to buy a boat somewhere between Maine and Florida and sail to the Caribbean.

I have another post that describes my sailing experience. Never any overnight or cruising...

So let's say I buy a boat somewhere on the Jersey shore. I leave harbor, turn right and head South. Then what?

Should I have planned anchorage for every night of the trip? Do I play it by ear and see where the day takes me? Inland waterway or ocean?

My guess is that it's at least three weeks to the Carribean if I start as far away as Maine...

Any input would be appreciated.

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Old 03-21-2008, 11:26 AM   #2
Join Date: Jan 2005
Posts: 97

Ensure you buy a suitable boat for what you intend to do; size, design and condition

Get some experience of that particular boat by sailing out of your home base

Go over the boat with someone who has long distance experience and identify and rectify weak points in design, equipment lacking and weak/old equipment

Get some rough weather experience (at least F5, preferably F7) by sailing out of your home base

Get some night sailing experience by sailing out of your home base

ALWAYS have a plan and alternatives, NEVER play it by ear. You might not keep to the plan, either because of choise or bad weather or damage/breakdown, in which case, make a new plan at that point.

Remember that you cannot readily call a breakdown service like you can in a car - are you able to tackle most failures of equipment while the boat is bouncing up and down (failures always occur at the worst possible moment)

I have not sailed in USA/Caribbean yet, the above is based on bringing a boat from Singapore to Turkey, with my wife. We were already both experienced sailors. We took a year to refit the boat for ocean sailing and get enough experience of it to feel comfortable for the Indian Ocean. Even if you go through the inshore waterway, you will have to do an offshore passage after that.

Peple who ignore the above points fall into one or more of three groups:

1 They are very lucky

2 They die

3 They cause the lifeboat/coastguard service a lot of extra work and expense

Hopefully, someone who already has experience of the area will add more specific advice

Good luck




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Old 03-21-2008, 02:10 PM   #3
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Posts: 2,098

You're right that it's at least 3 weeks away to the Carib., and if you're on a small sailboat that isn't good at going to weather, it can be a whole lot longer than that.

So let's take the East coast of the US first.

Winging it isn't going to work if you run into really bad weather. Many inexperienced skippers have lost their boat when they tried to take shelter in an inappropriate harbor when bad weather hits. There is virtually no safe entrance to NJ harbors for sailboats in bad weather. Most have bars across their entrance that become dangerous in easterly winds.

The same holds true on any section of the coast thereafter. Look at some charts, and see things like "Cape Fear", "Desperation Sound", etc.

You need to know where the safe harbors are before you start out. You should be very sure that you have access to good weather reports, and that you listen to them regularly. Sometimes you have no more than, or less than, 12 hours notice that things are going to get bad.

Secondly, offshore sailing is quite different from coastal sailing, and though you have to do it some time, I'm not that keen on jumping off with a two-week passage as a first experience. You will know your interests better than we can, so you should be looking at possible stops on your way south.

Some boats sail from Maine/NY/NJ or Chesapeake, over to Bermuda, regroup there, then sail to the Caribbean. It has lots to recommend itself. The difficult part of reach the Caribbean from further south, particularly Florida, is that you will have hundreds of miles of sailing into the wind, beating hard which isn't a lot of fun. Further north you can find better conditions to get your easting done to Bermuda after which the point of sail is usually a more comfortable reach.

Another option is almost day trips to the Caribbean, as described in Van Sant's "The Thornless Path", but it takes several months to do it this way.

And, of course, you need to know the seasons. One doesn't head to the Caribbean just before or during hurricane season, for example. One doesn't enter the Gulf Stream during a norther. Etc., etc.

Better to be prepared than unpleasantly surprised.

Fair winds,

In 1986 we went cruising for a few years. After 20 years and 50+ countries and several oceans, we are STILL "cruising for a few years".

MV WATERMELON (New) | Cruiser's Dictionary, free ebook

= Cruiser's Dictionary, North America,
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Old 03-21-2008, 02:38 PM   #4
Join Date: Mar 2008
Posts: 7

Thanks to both of you for the informative feedback. Your posts have lead to some 'decisions' and, of course some questions.

It sounds like it would be prudent to set up a temporary home base wherever I end up buying Ma Douleur and sailing day trips to get used to the boat before heading South.

When it's time to head South, I definitely agree that planning versus winging it is the way to go. Even if I stay local to where I buy the boat for a couple of weeks, I still think I want to go South as a series of day hops rather than immediately get into overnight solo sailing. When planning the trip for the day I guess I should look for a destination port that is 75% or less of the potential range for a day of sailing. With a 30' boat, sailing 12 hours a day, 100 miles should be a good target, no?

JeanneP said, "One doesn't head to the Caribbean just before or during hurricane season, for example. One doesn't enter the Gulf Stream during a norther. Etc., etc." How does one find out about these 'rules'? More specifically, hurricane season runs from June to November, right? My timeframe has me heading to / arriving in the Caribbean right around June. I know that St. Thomas almost never gets hit directly. The year that Katrina hit New Orleans, there were a zillion hurricanes and St. Thomas got hit with just a couple of rainy days out of it. If one doesn't go to the Carribean during hurricane season, where do they go?

As far as where to put in for planned and / or emergency situations, are there any good web sites that document anchorages, costs, etc.? Obviously charts show harbor locations but they don't show the practical information.

Thanks - Jake
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Old 03-21-2008, 03:23 PM   #5
Join Date: Sep 2006
Posts: 21
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One thing that I would like to add: If you intend to use the ICW, you HAVE to plan! There are some bridges that open at specific times. If you do not plan your trip, you can easily get "stuck" somewhere for a day or several hours. In the military, we had a particular acronym (one of thousands) "The 6 P" Proper Prior Planning Prevents Poor Performance.

In short, it is a romantic idea to just cast off the lines and sail away. Without SOME planning, you are asking for disaster of some sort.

My $.0002 worth...
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Old 03-21-2008, 08:04 PM   #6
Join Date: Mar 2008
Posts: 40

and remember, above all, have fun...

fascinating that there are people like me out there struggling to shove off ASAP. i realized (thank the monkeys for the interweb...it's a series of tubes you see) i needed to plan. so i developed a longer range plan (still 10 years to go). im most afraid of heavy weather, and realize i need to make sure my boat is bulletproof. also since i plan to singlehand, i have many other lessons to consider/learn. for instance i learned it's common for singlehanders to get any required sleep (if you can) during the day. only catnap at night. also a singlehander should probably invest in some 'fancy' electronics to help alert you to things you might not be focused on at a given moment, also a windvane/autopilot combo, there are a lot of jobs that have to be performed that aren't at the helm. also be sure you know how to heave to properly (i hear each boat has it's own personality along these lines). in short, i'll need a tough(er) boat, extra gear, and a good realization of how my natural requirements (eat, sleep, etc) will have to be accomodated in as safe a manner as possible 24/7.

12 hours...100 miles....is possible, but depends on the boat design (which is a pretty fast boat i think)...and the weather. i think 5-7 knots avg speed is more common...im speculating from my limited experience.

good luck though. you don't know how much i wish i were you.

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