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Old 27-05-2024, 17:02   #1
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1 season in the Caribbean, what would you do?

I am going to take a sabbatical for one season at work. November - May and buy boat and spend the time in the Caribbean (yes, I have sailing experience). So far of the people I've spoken to there have been two suggestions

1) Spend the whole season in the Bahamas.
2) Join the Salty Dawg rally down to Antigua and then spend those 6 months traveling back north.

If you were doing this and starting to plan it, what would your route/itinerary be or what other suggestions would you have?
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Old 27-05-2024, 17:44   #2
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Re: 1 season in the Caribbean, what would you do?

On such a tight timeline I think it will be very hard to find and buy the right boat and then get her fixed up for cruising. I have yet to purchase a boat that didn't take me 6 months to two years to get to the point where I could take off. But, it might be possible if you bought a boat in Florida where you will have much better access to supplies, boatyards, and repair people, and at much lower prices than down in the Caribbean. Then use any extra time to cruise the Bahamas.
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Old 27-05-2024, 18:20   #3
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Re: 1 season in the Caribbean, what would you do?

It depends on what sort of pace you want to set. Some people sit in Georgetown in the Bahamas for the whole winter and couldn't be happier. If you get bored after 3-4 days in the same spot then a fast tour of the Caribbean might suit you fine. Is your wife/girlfriend going with you? If so, definitely Bahamas.

But neither plan is going to work if you buy the boat in November. Buy it right now fairly close to where you live and start getting it ready for the trip. Do weekend shakedown trips to see what needs fixing and improvements. Like "new foam for the beds because the 15 year old foam makes your back hurt". Then there's always lots of waiting for parts to arrive and the yard to schedule you.

And don't buy a "project boat" - those take over a year to get ready. Buy one that's "ready to go" and still expect to spend $50k above the cost of the boat by the time you push off.
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Old 27-05-2024, 19:06   #4
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Re: 1 season in the Caribbean, what would you do?

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It depends on what sort of pace you want to set. Some people sit in Georgetown in the Bahamas for the whole winter and couldn't be happier. If you get bored after 3-4 days in the same spot then a fast tour of the Caribbean might suit you fine. Is your wife/girlfriend going with you? If so, definitely Bahamas.

But neither plan is going to work if you buy the boat in November. Buy it right now fairly close to where you live and start getting it ready for the trip. Do weekend shakedown trips to see what needs fixing and improvements. Like "new foam for the beds because the 15 year old foam makes your back hurt". Then there's always lots of waiting for parts to arrive and the yard to schedule you.

And don't buy a "project boat" - those take over a year to get ready. Buy one that's "ready to go" and still expect to spend $50k above the cost of the boat by the time you push off.
Thanks. Yeah. I'm already working on the boat buying and planning to have one closed on before July/August and moving aboard in September. Def not buying a project boat either!
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Old 28-05-2024, 08:53   #5
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Re: 1 season in the Caribbean, what would you do?

It looks like you'll be buying on the east coast. Have you thought of buying in the Caribbean somewhere (St. Martin, BVIs, St. Thomas)? Since you'll only be sailing for six months, might you find a boat coming out of charter (and therefore somewhat refitted for a six month trip) in one of these locations. The boat may not have everything someone would want for a six year cruise, but for six months you don't need much. All of the sailing is basically line of sight and if you can at least read a chart and map (which it sounds like you can), you can easily sail from any of these down and back up.

The advantage is you wouldn't have too much to worry about on the boat. There are FB pages that tell folks experiences of buying a charter boat and you can research through those on which companies to consider. A good company would help direct you on the proper paperwork you need to bring it back to the US (and possibly to do the initial registration in the US.

If you start in the US and finish in the US, you're sailing is twice as long as it might need to be.

Just a thought (from a non-experienced boat buyer - so take everything I wrote with a grain of salt. It may be a horrible idea.)
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Old 28-05-2024, 08:59   #6
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Re: 1 season in the Caribbean, what would you do?

Where is your boat located? That will make a big difference to where you might go. The Bahamas contains something like 700 islands spread out over 700 miles, so there is plenty to see there during a six-month cruise. Plus, you have the advantage that Florida is reasonably close for those inevitable new-boat-to-you things that need to be fixed or replaced.
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Old 28-05-2024, 10:04   #7
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Re: 1 season in the Caribbean, what would you do?

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Where is your boat located? That will make a big difference to where you might go. The Bahamas contains something like 700 islands spread out over 700 miles, so there is plenty to see there during a six-month cruise. Plus, you have the advantage that Florida is reasonably close for those inevitable new-boat-to-you things that need to be fixed or replaced.
I'm looking at three boats right now. One that's in VA and two in TX. I'm leaning more towards the VA boat.

After all the replies, I'm leaning more towards just staying in the Bahamas for this first season and seeing how things go.
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Old 28-05-2024, 10:13   #8
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Re: 1 season in the Caribbean, what would you do?

Couldn't agree more. B'mas is easy to get too from the US eastern seaboard.

The Caribbean not so much, as that would take a 7 plus days of hard on the wind sailing direct, and at least a month of island hopping.

Having been to both places numerous times, B'mas gets my vote hands down. There are so many island chains and different islands, you'll never get bored.
Fishing and diving is excellent.
You can chose to take the path less travelled or join the herd in George Town, or do both.
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Old 28-05-2024, 12:41   #9
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Re: 1 season in the Caribbean, what would you do?

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Couldn't agree more. B'mas is easy to get too from the US eastern seaboard.

The Caribbean not so much, as that would take a 7 plus days of hard on the wind sailing direct, and at least a month of island hopping.

Having been to both places numerous times, B'mas gets my vote hands down. There are so many island chains and different islands, you'll never get bored.
Fishing and diving is excellent.
You can chose to take the path less travelled or join the herd in George Town, or do both.
Thanks! So, would it be smart to sail from VA down to Abacos in NOV then work my way back up north?
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Old 28-05-2024, 12:53   #10
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Re: 1 season in the Caribbean, what would you do?

Bahamas and Caribbean are worlds apart. Your plan works for Bahamas, but not for Virgin Islands to Trinidad.

If you want to do the CARIBBEAN then buy a boat THERE. You can then sail West to the Bahamas and back to the states, easy peasy. Sailing EAST from Bahamas to VI’s SUCKS and will kill your trip.

I would look in Trinidad, Grenada, and Carriacou. Then you have the whole chain ahead of you as you head back West. For reference we sailed Dominica to North Carolina in 13 days. So the end is always in sight heading West.
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Old 28-05-2024, 13:30   #11
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Re: 1 season in the Caribbean, what would you do?

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Thanks! So, would it be smart to sail from VA down to Abacos in NOV then work my way back up north?
Yes, but particularly with a new boat I would suggest coastal hopping and using the ICW to get down to Palm Beach, and then make the crossing to the Abacos. Or, if the weather is no good when you get to Palm Beach keep heading south in Florida until you get a weather window, and then maybe cross to Bimini and keep on going south--you can hit the Abacos on the way north again. With a new boat you'll want to stick close to the USA until you have most stuff sorted out. Heading offshore on a new-to-you boat is a recipe for disaster.
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Old 28-05-2024, 15:21   #12
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Re: 1 season in the Caribbean, what would you do?

Black c 2004 we’ve had the same idea for a while. But coming from Australia we’d prefer to start south by buying a boat in Trinidad/Grenada or Virgin Islands and head north, selling it in Florida. As mentioned above you would be doubling your distance by heading south, then returning north ! We haven’t done the Bahamas, but have lived in the Caribbean for ten years and the variety offered there by the different island /cultures warrants another (ten year ?) visit
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Old 28-05-2024, 16:08   #13
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Re: 1 season in the Caribbean, what would you do?

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Black c 2004 we’ve had the same idea for a while. But coming from Australia we’d prefer to start south by buying a boat in Trinidad/Grenada or Virgin Islands and head north, selling it in Florida. As mentioned above you would be doubling your distance by heading south, then returning north ! We haven’t done the Bahamas, but have lived in the Caribbean for ten years and the variety offered there by the different island /cultures warrants another (ten year ?) visit
Bingo!
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Old 28-05-2024, 17:57   #14
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Re: 1 season in the Caribbean, what would you do?

If it were me, I'd consider going a little earlier than Nov from VA, primarily as sooner or later you will have to cross the gulf Stream, which can get boisterous in a nor-easter, which start to crank up around Nov.
If you are comfortable going offshore and time your weather right, it can be a sleigh ride down the coast of the US. Florida can be reached in a matter of days.

Off course, Nov is still hurricane season, so you have to throw the dice, but typically you'll have plenty of notice of any impending 'cane.

I don't personally like the ICW and try to avoid it, though I did once do the ICW from North Florida to Chesapeake Bay. That took a month, motoring all day long, each day. Add another week to get down the coast via ICW to WPB or thereabouts.

I have crossed over to the Abaco's many times leaving from many different ports, inlets, etc. Again, one needs to watch the weather and pick an appropriate weather window.

Quite frankly, my best B'ma cruises were from Feb thru' July/August. Insurance requirements may dictate otherwise, but I don't let insurance dictate my cruising options. But that is your call.

Abaco's are the northernmost B'ma chain. Once you leave there, nothing but water between there and VA.

Popular jumping off points for the Abaco's are most any inlet south of Cape Canaveral, including CC. Ft. Pierce and WPB are popular jumping off spots.

The big bugaboo about sailing in the B'mas during the winter time are the nor-easters. These can and do sweep way down the island chain. If you time them right, you can use them to your advantage, otherwise you'll be in for a hard bash.

It's difficult to provide guidance as I don't know you, your sailing skills, preparation of your boat, crew, etc.

Quite a few boats head to the B'mas every year. Best advice I can give you is give a shout on the vhf and see who is going where and tag along with someone. Odds are you'll find one or more boats going there.
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Old 31-05-2024, 15:51   #15
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Re: 1 season in the Caribbean, what would you do?

I don’t understand how to ‘buy a boat in the Caribbean and sell it in Florida’’. Buying a boat is complicated, no? You have to go there and look until you find one, then get it surveyed and fixed up, then pay taxes and get it registered and insured. That process could take months. And then there is the cost of selling-getting a mooring or having her pulled for bottom cleaning, paying a broker, pay UStaxes. and selling is getting harder and harder. How much time will be left for sailing?
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