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Old 11-05-2015, 23:09   #1
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Am I dreaming too big?

One item on my bucket list is to sail around the caribbean for a few months. Let me state this first, I have never sailed a boat but love the allure of it.

How does this sound.
-I take sailing lessons and when i feel ready I purchase a small sail boat. Probably in the $10,000-$15,000 range. Something I will probably have to handle by myself (I don't need a list of recommended boats. There are pages and pages of those). I sail south from North Carolina through the intercostal waterway. When the weather is right I take the plunge from southern Florida to my next destination. I've been a planner my whole life and taken great care to make the best preparations for each endeavor I undertake. This way I am prepared for an inspection by coast guard, weather, engine failure, etc.... I do this for a few months. Get my fix. Then sell the boat. Even if I have to take a 20%-50% loss when i sell the boat it will be worth it for the 3-6 months of experience I have. I don't care to sail for the next several years. Just long enough to get it out of my system.

You guys are the pros here. What are you opinions?

Thanks
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Old 11-05-2015, 23:16   #2
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Re: Am I dreaming too big?

That is a much sounder plan than most that come through this forum. 10-15K can get you a good amount of boat (I don't know what you consider "small") in decent shape, which is all you need for what you plan to do. Sailing lessons are a good idea, so you know what you're getting into. That's what everyone says anyways. Personally, before I bought my first boat I'd only ever sailed on a Sunfish, and I didn't like that very much. But once I got the idea into my head it stuck and I've been sailing ever since. Preparation is absolutely key, you can do almost anything in almost any boat with the proper amount of preparation.
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Old 11-05-2015, 23:18   #3
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Re: Am I dreaming too big?

Be careful, it is addictive. The reason that there are no 12 step programs for sailors, is that nobody would want to attend them. DO IT AND HAVE A GRAND TIME. _____Grant.
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Old 12-05-2015, 00:44   #4
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Re: Am I dreaming too big?

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Originally Posted by donkey_jaw View Post
I don't care to sail for the next several years. Just long enough to get it out of my system.
Funny things, itches. Some require considerably more scratching than one might first think.
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Old 12-05-2015, 07:38   #5
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Re: Am I dreaming too big?

Yeah. Who knows I may love it and then decide to keep or buy another. I live several hours from the beach but that ok. The more difficult a goal is, the more you enjoy it when you've achieved it.
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Old 12-05-2015, 09:43   #6
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Re: Am I dreaming too big?

donkey_jaw - not too big but you need to be realistic. And I am not coming at this as an expert - I am officially a lurker here, reading every day and learning.

I would suggest checking out youtube for a guy that goes by the name of Wicked Salty. There are other youtube blogs about the sailing life, but this guy's posts start with acquiring a boat, all the things that go wrong, and all the things that go right. Highly informative.

Live your adeventure
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Old 12-05-2015, 09:49   #7
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Re: Am I dreaming too big?

Always remember, with boats, you can plan, but you can't plan outcomes.

I think you're taking the right steps. you can get 26 to 35 foot used older sailboat already rigged for single-handed sailing in the price range you're working with.
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Old 12-05-2015, 09:49   #8
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Re: Am I dreaming too big?

The plan has merit if you can remain "clinical" in your approach. After 40 + years of sailing (racing and cruising) I have yet to meet anyone who got it "out of their system" except old sailors who switch to power boats. PERHAPS a different approach for a short term sailing adventure: how about chartering a small boat already in the Caribbean ($15K would go a long way) and or signing on as crew on a larger boat. Like marinas everywhere there are boats sitting owned by someone unable to use them. Working on larger boats can be fun and give you unforgettable experiences. Advertise in sailing rags, check blogs and websites, put the word out. You will find opportunity.
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Old 12-05-2015, 10:12   #9
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Re: Am I dreaming too big?

My husband and I started sailing 6 years ago without having ever sailed before in our life! We are still learning but it's been an enlightening experience to say the least. There are some great blogs out there that will keep you excited about the process. Windtraveler.net is a good one with great writing and photos. I also started doing a blog with our last sailboat (mountainsandseashore.blogspot.com) we brought down the Intercoastal Waterway. We are now on the hook in St. John in the Virgin Islands and enjoy sailing around the British Virgin Islands and the Spanish Virgins but are looking forward to sailing down island next year.

Be careful, once you start sailing you'll never fit into normal society again. Suburbia will never hold the same allure ever again.

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Old 12-05-2015, 10:53   #10
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Re: Am I dreaming too big?

Why would you Want to "get it out of your system"....you have been bitten by the Sailing Bug.....

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Old 12-05-2015, 11:23   #11
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Re: Am I dreaming too big?

Quote:
Originally Posted by hyperfine View Post
Funny things, itches. Some require considerably more scratching than one might first think.
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Old 12-05-2015, 11:26   #12
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Re: Am I dreaming too big?

This is a perfectly reasonable plan.

When you're planning, don't forget that you need to plan around hurricane season (June-ish to October-ish).

Beth Leonard's Voyager's handbook is an excellent source for the cruising knowledge you need.
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Old 12-05-2015, 11:37   #13
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Re: Am I dreaming too big?

Thanks for the advise guys. I will not be sailing during hurricane season. If I do try this I will begin after the season ends. Working on a big boat that someone else owns sounds nice and I will gain lots of experience while being around seasoned sailors but I want to go where I want to go when I'm ready. If that makes sense. Also another "IF" here, if I do this then I probably will have to quit my job and and take a few months off while not bringing in any income.

If I really enjoy this my next step in a few years will be to join a larger boat as crew and leave from somewhere in the west coast possibly south america and sail throughout the pacific for a few months.
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Old 12-05-2015, 12:28   #14
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Re: Am I dreaming too big?

I'm helping a friend sell a Grampian 23, very good condition, great little boat to single hand, ready to go, very sturdy, and lots of room for a small boat, complete live aboard, head, galley, etc. it's $900 without the engine, but the engine and trailer are available. It is shallow draft, good for the Caribbean, buy it, get a new battery and a small outboard, and you can be sailing tomorrow for under $1500. See it at my website

For Sale 3

I could even spend a couple days teaching you how to sail.

If interested act fast and let us know, the owner is getting ready to donate it to a church.
Jon
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Old 12-05-2015, 14:37   #15
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Re: Am I dreaming too big?

donkey_jaw wrote:

> I've been a planner my whole life and taken great care to make the best preparations for each endeavor I undertake.

Good. This approach of trying to understand what you are about to do reduces the probability of bad mistakes a lot.

> Even if I have to take a 20%-50% loss when i sell the boat it will be worth it for the 3-6 months of experience I have.

This part is not as good. This sounds like you are in a hurry, and could therefore take risks just to get the thrill and adventure.

If I were you, I would reserve some more time for some small trips, aimed at getting familiar with the boat, and getting lots of small scale experience before taking the next bigger steps.

But if you know what you are doing, just go ahead. If you know that you practically never rush into actions that you might regret later, then you are probably ok. The biggest risk I see is taking risks and jumping into situations that one does not master. A good captain aims at 200% control (= with 100% error margin) of all possible emerging situations.
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