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Old 19-07-2015, 11:00   #1
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Best City to Learn to Sail, Work and Live Cheaply

In about 10 months time, I am going to take the plunge into fulfilling my dream of living in the Caribbean and sailing around the world. I am looking for the best state/city/town to help me reach these goals. I have no sailing experience, but have been on/near water and boats most of my life. I am tired of the cubicle gig and yearn for a lack of routine.

What are some good options for a location with a relaxed vibe, lots of friendly sailors, and at least a seasonal job market?

Nothing to ruin a beautiful spot like lots of people, so would prefer to stay away from the big city, but I am relatively flexible. Doesn't have to be on the East Coast, but I do prefer warm water.

Been reading every sailing book I can get my hands on, just looking for advice on my next big move. Would love to spend about a year learning to sail and finding a boat to fix up, just not sure where to start.
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Old 19-07-2015, 15:50   #2
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Re: Best City to Learn to Sail, Work and Live Cheaply

Auckland, NZ?
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Old 19-07-2015, 16:29   #3
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Re: Best City to Learn to Sail, Work and Live Cheaply

San Francisco. We have wind here during the summer (except for today - 90F and NO breeze - some tail of some zeehag furrycane ).
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Old 19-07-2015, 17:01   #4
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Re: Best City to Learn to Sail, Work and Live Cheaply

In US-probably Seattle.SF cost of living through roof.Seattle really easy peasey afternoon crew sails to find.Actually,there's an APP.for sail hookups there !


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Old 19-07-2015, 17:46   #5
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Re: Best City to Learn to Sail, Work and Live Cheaply

Just about any city on a major body of water will have some level of sailing. I live in a big city by one of the Great Lakes. Sure my season is only 6 months but it's fun and challenging. No tides or salt either. We have some top-notch sailing schools and several active yacht clubs.

For the learner, every body of water is going to have challenges and experiences to offer. Many of us sweetwater sailors also head south for at least part of the winter.
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Old 19-07-2015, 18:28   #6
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Re: Best City to Learn to Sail, Work and Live Cheaply

He said Carribbean in 10 months.
Depends on your skills, but St. Thomas may be a good start.
Lots of boats and sailing there, also jobs, kind of.
Waiter or bartender come to mind first.
Depends on your skills.
Dive Instructor maybe.
I worked there as an airplane pilot while living on a boat.
Crappy place after a while, but perfect weather, perfect sailing and perfect diving.
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Old 19-07-2015, 18:39   #7
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Re: Best City to Learn to Sail, Work and Live Cheaply

Where is best kind of depends on what you do for work.
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Old 19-07-2015, 18:44   #8
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Re: Best City to Learn to Sail, Work and Live Cheaply

Doesn't have to be in the Caribbean, but the closer the better. Mainly looking for a town with lots of boat yards, lots of sailboat traffic, at least a few sailing clubs, and a more laid back boat culture.

While I will keep San Francisco and Seattle in mind, I do prefer warmer water. I am currently a PADI Dive Master, so that is one option for employment.

Really appreciate the input. I am leaning towards Florida, just not sure what town yet. I currently live in Coastal North Carolina, but am pretty eager to try somewhere new.
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Old 21-07-2015, 12:09   #9
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Re: Best City to Learn to Sail, Work and Live Cheaply

Astoria is ten degrees warmer than Seattle, but is still dry suit diving. Living here is easy. I think he ought to look at the Texas coast. Lots of jobs.
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Old 21-07-2015, 15:43   #10
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Re: Best City to Learn to Sail, Work and Live Cheaply

St Augustine is a nice little town. Tourist traffic can get heavy at certain times of the year but it's a far cry from rush hour in Jacksonville, the closest big city, 45 miles to the north. I count 7 marinas, 2 sailing clubs and 2 sailing schools. Anchorage and mooring is an option as well.
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Old 21-07-2015, 17:02   #11
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Re: Best City to Learn to Sail, Work and Live Cheaply

Really appreciate the input everyone.

I am currently a low-level white-collar project manager at a fortune 500 company. Overworked and underpaid and tired of the monotony.

I am hoping to find a 27-32 foot bluewater boat for around $10k. I know it will take me a while to find one, which is why I would like to maximize my chances by living in a town with lots of boat traffic and a diverse boat for-sale market. Plan is to learn to sail and work on boats until I can find one.

Any other ideas? St. Augustine is right up my alley. I also have family in the greater Miami Beach area, but could never stand to live there, but wouldn't mind something not too far like Cape Coral or Sarasota, just not sure how the sailing is there.
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Old 21-07-2015, 17:59   #12
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Re: Best City to Learn to Sail, Work and Live Cheaply

Quote:
Originally Posted by StuM View Post
Auckland, NZ?
Exactly what I'm doing and where I'm doing it (well the learning to sail part anyways). It's fantastic, lots of very friendly and helpful sailors! The only problem is that right now it's cold and so is the water, give it a couple of months!
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Old 21-07-2015, 18:02   #13
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Re: Best City to Learn to Sail, Work and Live Cheaply

As in multihulls, you can only have two out of the three.....


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Old 29-07-2015, 10:17   #14
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Re: Best City to Learn to Sail, Work and Live Cheaply

Have you visited Oriental, NC? There's a sailing school there, weekly races, lots of transients to regale you with stories of the cruising life, and the cost of living isn't too high.
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