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Old 10-07-2019, 12:37   #1
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sail carribean single-handed for one season?

Given the facts of my life, I don't think long-term boat ownership is for me. (Married, spouse likes sailing enough to charter sometimes, but probably not interested in long-term living on a boat. Also two cats at home who'll hopefully be around for another decade or so. Live in Boston, so keeping a boat along with the apartment here seems too expensive.)

So I've been daydreaming about spending a few months sailing in the Carribean - probably mostly myself, but with my spouse and friends joining for parts of it.

I'd love to get some advice about:

- whether this seems feasible
- how to pull it off smoothly
- anything you can point me to about anyone else doing something similar

Some of my own thoughts so far:

- I'm thinking the boat would be a monohull, roughly somewhere in the 30ft-38ft range. I'd love to have other suggestions about what I'd be looking for. Definitely need a bimini or dodger. Solar panels would be nice but if it doesn't happen I could charge via diesel, and try to minimize power usage. Wind vane self steering.
- I'd take a few months off work (either leave of absence, or do it between jobs).
- I'm expecting I'd probably have to buy a boat and resell it later, although it'd be great to find a way to do this without purchasing (e.g. if I'm somehow lucky enough to find someone who trusts me with their boat for awhile, in exchange for giving them some money).
- I know not to expect to recoup my full investment if I buy and sell a boat - I'm thinking of this as a long vacation, and I understand that it will cost money.
- I guess that means I might be buying the boat sight-unseen, which sounds tricky but I've heard it can work out.
- I'd probably aim to start in the Windward Islands and avoid beating to windward. Or start in the USVI or Puerto Rico and head windward. Either way, the longest passage is between BVI and Anguilla. Everything else can be done entirely during daylight, I think. (I've read that some of the passages are more difficult if I were to start west of Puerto Rico.)
- I probably want a bit more sailing experience than I have now, which is OK since my work situation would probably have me waiting a year or two anyway.

Some notes about my experience, in case that helps anyone advise me:

- I've never owned a boat
- I race small boats often
- my bigger-boat (30ft+) experience is limited to 1 week chartering in the BVIs, and a bunch of daysails/overnights near Boston
- I'm really not very handy at fixing stuff
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Old 10-07-2019, 12:44   #2
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Re: sail carribean single-handed for one season?

Oh, and of course I'd like to get a bit more experience first by crewing for someone (maybe from this site, maybe elsewhere). In the Carribean or elsewhere.
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Old 10-07-2019, 12:45   #3
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Re: sail carribean single-handed for one season?

Learning to cruise by doing something along the lines of what you propose is not a problem in the Caribbean - many here have done the same. I took lessons and bought an ex-charter boat and have singlehanded for about 6 months out of every year since then. I sold my first boat, a 43DS, in the BVI to a Canadian who had never sailed but wanted to spend a year cruising with his wife and 2 kids. He was not technologically minded, I had to explain the difference between the AC and DC circuits on the boat.

But he bought the boat, took some lessons and then I buddy-sailed with him and his family down the islands!

One of the major deciding factors is the cost of the boat that you have budgeted and what your monthly expense budget is. If you have severe restriction on the boat price, then your starting location will be determined by where you find the boat. In this case yachtworld is your friend. That will give you an idea of how far your boat buying dollar will go and if you limit the searches to the Caribbean Islands then you'll also see where your future boat is located.

Not being handy at fixing stuff is a condition that changes quickly when you own a boat! The important question is do you dislike fixing things? If yes, then expect to pay over $100 per hour for someone else to fix your problems.
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Old 10-07-2019, 15:29   #4
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Re: sail carribean single-handed for one season?

Get a trailer sailer like a C&C Mega 30, Lugar 30 or misc others.

Outfit it on your own turf at your own pace and get experience sailing that boat.

Trailer it to Miami and sail down from there.

Best bet would be to ship the boat back from PR or USVI then you are not using cruising time to retrace your path. $2-4K. You could ship it down and sail back but thatís more expensive.
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Old 10-07-2019, 16:51   #5
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Re: sail carribean single-handed for one season?

Buy a boat that is down in Guatemala already. Then you can sail around Belize etc and figure things out. Trust me, anyone can do it. Then take the boat back to GUA for $5 a foot per month when you need a dock.
It's easy to fly to Belize. My wife can make it in one day from small town Oregon, USA to anywhere they have an airport in Belize. They only fly VFR, so you get to the boat in the late afternoon, not bad.
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Old 11-07-2019, 09:15   #6
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Re: sail carribean single-handed for one season?

My suggestion:
Find an older 35 to 40 ft boat for 30k in florida that has been on the market for a while, offer them 10K cash. put the boat in the yard, do the bottom, etc. yourself (trust me, you will have plenty of advice from everyone if you ask how to do something). Keep the boat simple, clean and inexpensive. Depth sounder, simple VHF, simple chart plotter (you can buy a combo depth/chartplotter for around 200 bucks) simple autopilot, propane deck bbq, buy a good dingy with a good engine, and make sure you have a good (simple) refrigeration system (you donít need a freezer).

Always think clean and simple. Donít go overboard on gadgets, safety gear, or electronics.

Find someone to help you deliver the boat to the West Indies (Antigua, West End, wherever). Pay attention and you will have learned enough on that trip to sail single handed and not be worried about sailing at night. (yes, it is a beat, you will get sea sick, it will be uncomfortable, but thousands of people have done it, you can too, and you will have fun)..

Have fun in the islands, keep everything simple, when you tire of it, sell the boat.

Just keep things simple.
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Old 11-07-2019, 09:33   #7
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Re: sail carribean single-handed for one season?

I think it's feasible. Don't overdue what you need on the boat for this type of thing. Most of the E. Caribe is overnighters at worst. KISS. A good production boat is fine. 32-36 ft? I'd probably go with no watermaker, alternator charging scheme.
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Old 11-07-2019, 13:17   #8
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Re: sail carribean single-handed for one season?

Zanshin: Nice story about buddy-sailing with your boat's new owner. I love that stuff!

Quote:
One of the major deciding factors is the cost of the boat that you have budgeted and what your monthly expense budget is.
The boat cost itself isn't very important to me, only how much I've spent on the whole endeavor at the end. So e.g. if I buy a boat for $50k, put $10k of work into it, and can sell it later for $50k... that's better than buying for $20k and not being able to sell at all.

Quote:
The important question is do you dislike fixing things?
To be honest, in my life I mostly haven't loved tinkering with physical stuff (I'm a programmer), but so far I've enjoyed everything to do with sailboats, including some minor mechanical stuff. So hopefully I wouldn't mind it! I can imagine loving the boat, and therefore loving taking care of her. If I do end up paying a lot for help, that's not the end of the world. If I learn that I dislike it, then I'll still have had fun but will know that cruising isn't for me.

Adelie: I appreciate the tip, but a trailer doesn't really sound feasible. My Boston apartment has a tiny driveway, barely big enough to fit a Laser on a trailer. Nowhere to put a trailer boat, so I don't think that simplifies anything.

Ecos: Love your thinking! $5/foot/month? Wow. That's cheap!

Cheechako: Thanks!
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Old 11-07-2019, 13:19   #9
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Re: sail carribean single-handed for one season?

captmikem: Buying in FL sounds sensible. Is your thinking that it's better that way (instead of buying in the Caribbean) because FL is closer to me so figuring out the details will be easier? Or because it'll have more boats for sail?

I do like the idea of paying for a delivery with me on board, to get some experience.

Actually, would it be feasible to buy a boat in Boston and pay for a delivery from here (with me onboard)? I know people who would probably do that with me...

But I guess I was assuming that would require a boat that's sturdier and more expensive than I really need? (And put a lot of wear on the boat?)

That could give me some time to work on the boat, and sail locally, before leaving my job for longer.
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Old 11-07-2019, 13:50   #10
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Re: sail carribean single-handed for one season?

Quote:
Originally Posted by Exonerated View Post
captmikem: Buying in FL sounds sensible. Is your thinking that it's better that way (instead of buying in the Caribbean) because FL is closer to me so figuring out the details will be easier? Or because it'll have more boats for sail?

I do like the idea of paying for a delivery with me on board, to get some experience.

Actually, would it be feasible to buy a boat in Boston and pay for a delivery from here (with me onboard)? I know people who would probably do that with me...

But I guess I was assuming that would require a boat that's sturdier and more expensive than I really need? (And put a lot of wear on the boat?)

That could give me some time to work on the boat, and sail locally, before leaving my job for longer.
The reason I say Florida is because it is FULL of boats like you are looking for (for instance a friend bought a nice 42ft boat that was listed around 35K, he offered 7K for it and sailed away with it. Check with the brokers, craigslist, and even ebay. Seriously, there are hundreds of boats there that are good, built in the 70's and 80's that sit behind someones house or in a marina that are available. There may be boats like this in Boston but I do not know that. In Florida, they exist in JAX Ft. Lauderdale, Miami, all up and down both coasts.

No, it would not put more wear on the boat, boats are made to be sailed, what little wear you might put on the rigging and sails would be negligible on a trip from Boston to the Virgins. Same from Florida, just a LOT more boats available in Florida.
Good luck with your adventure.
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P.S. Stay away from teak decks.
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Old 11-07-2019, 13:51   #11
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Re: sail carribean single-handed for one season?

Quote:
Originally Posted by Exonerated View Post
Actually, would it be feasible to buy a boat in Boston and pay for a delivery from here (with me onboard)? I know people who would probably do that with me...

But I guess I was assuming that would require a boat that's sturdier and more expensive than I really need? (And put a lot of wear on the boat?)

That could give me some time to work on the boat, and sail locally, before leaving my job for longer.
I don't have personal experience there to offer, but I can say that I've read that advice before - the tropical sun and heat are hard on boats. If you buy up north, you're likely to find a boat that's been sailed a lot fewer hours and been smacked around by several fewer tropical storms than a boat of equivalent age that's been cruising the Caribbean for all of that time.


And I can say I DEFINITELY would be in favor of getting the boat into your hands a few months sooner and getting to do some weekend sails to learn your way around it. Halfway to the Bahamas is a REALLY crummy time to be trying to get the old owner on the sat phone to ask "Is there usually this much water coming into the bilge? Where's the seacock for the head? I've looked under every bench!" Spending a season sailing it... finding the little problems... learning how every system works... doing a bit of maintenance yourself... that time will be valuably transformative for both the boat and the sailor.
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Old 11-07-2019, 14:10   #12
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sail carribean single-handed for one season?

Good advice above I think. I agree that keeping it simple is a good thing. I do think, however, that buying stateside might not give you the best opportunity for easy access to the islands. There are a lot of boats in Trinidad, Grenada, Martinique and St. Martin for sale too, and these ones have the advantage of already being where you want them to be without having to beat to windward for weeks, or months.

Yes you can day sail all of it, including the passage between St Martin and the BVIs, just. Itís 85 miles from Marigot to Virgin Gorda, which is a 16-hour day at 5.5 knots. Even west to east itís doable if you have the time to wait, as the wind does sometimes come around to the north or north east.

Anyway, yes itís totally feasible. In fact I canít think of anywhere in the world that is better suited to what you are suggesting. Go for it!
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Old 11-07-2019, 14:20   #13
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Re: sail carribean single-handed for one season?

Quote:
Originally Posted by DefinitelyMe View Post
There are a lot of boats in Trinidad, Grenada, Martinique and St. Martin for sale too, and these ones have the advantage of already being where you want them to be without having to beat to windward for weeks, or months.
These locations are the capitals of the broken dreams, where wifie has said enough is enough. It's very likely that the boats will already be fully loaded with cruising toys eg solar, watermaker, snorkeling gear, plus several tins of baked beans and a decent supply of rum
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Old 12-07-2019, 00:58   #14
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Re: sail carribean single-handed for one season?

Definitely buy the boat in NE, dock near Boston and spend a year sailing locally, cruising overnights as much as possible.

Why?
1. You have time before you want to quit job.
2. Get to know boat, fix things.
3. Parts are easily available in USA.
4. Huge selection of boars.
5. Not a big deal to sail to FL in short hops.
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Old 12-07-2019, 06:43   #15
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Re: sail carribean single-handed for one season?

Avoid buying a boat if possible. I would contact sailboat charters in the BVIĎs. You should be able to work out a long-term charter. I would do it by the month with the right to extend. I suggest that because this dream could last six months a lifetime or 30 days. After 30 days experience in the BVIís the charterer may expand your sailing grounds to PRVI or St Maarten or beyond.
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