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Hi there!
Although my dream is a few years away at the least, I want to start building a skill set and knowledge base for when the opportunity comes for me to buy my own vessel. I have 10+ years of sailing experience on everything from optis to schooners and back again, US Sailing Level 1 Instructor, and I have a US Sailing Keelboat certification under my belt. I live in Boston and have access to dinghys, some J boats, and a whole season of free time ahead of me. Can anyone recommend the best place to get started?
 

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Welcome to Sailnet. You found one of the great place to start.

Un-like you I had very little sailing experience before becoming a full time cruiser, but sites like this made getting the knowledge and answers I needed along the way.
 

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Wandering Aimlessly
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The first step is getting a clear and realistic vision of your intended cruising. Cruising is something with many "definitions", so until you settle on the definition that best describes your plans, it's hard to know what you need to know against what would be good to know.

More generally, it's hard to go wrong with Nigel Calder's Cruising Handbook as a starting point.
 
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My advice, buy a cheap beater boat right now. Soething in the 25' to 30' range (big enough to support overnighters and multi-day trips) that can be sailed as is, but could use some maintenance, upgrades and repairs. Then for the next few years be fixing it up while you sail it. Take longer and longer trips, learn navigation, heavy weather sailing, repairs underway etc. Then in a few years when you're ready to really dive in to the cruising world, you sell that boat (hopefully at a decent price considering the years of elbow grease you've invested in it), buy the real cruising boat of your dreams, and live happily ever after.

Keep in mind that actually sailing a boat is only a small part of the cruising lifestyle. There's the old addage: "Cruising is fixing your boat in exotic locations".
 

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Living the dream
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sarcasm /on
Where to start? Stand in a cold shower and start tearing up $100 bills
sarcasm /off

You already have sailing experience, you just need to add the extras. I'd agree with wristwister and say other important areas are learning repairs and maintenance, navigation and passage planning and basically learning how to spend a few days or more on a boat. My wife and I started with a beater trailer to learn the basics on.
 

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Dr. Strange,

Do you own a boat ? If so, and if you do have an entire season, head down east. That will take you north through/past NH, southern Maine, Saco Bay, Casco Bay, Sheetscot Bay, Linekin Bay, Johns Bay, Muscongus Bay, Penobscot Bay, and a couple of dozen others. That's 4600 islands and 3500 miles of convoluted coastline, one of the most beautiful cruising areas and arguably most challenging with our ridges, reefs, winds, fog, 13 foot tides and veritable virus of lobster buoys.

Don
 

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I would suggest you offer yourself up as free delivery crew (not captain) on cruising boats doing crossings or whatever. This will give you a number of cruising designs to sample w/o spending your own money and a chance to learn from those who are actually cruising. Whatever your skill level from schooling, the practical will be an eye opener and a variety of captains will hopefully broaden your knowledge, as there are as many ways to skin a cat as... you get the idea.
 

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It really isn't as glamorous a life as one would be led to believe. If you sail the tropics, its hot, you dont have A/C, your fridge constantly breaks, the beers sometimes warm....the people that live shoreside dont want you anchoring there. Marinas are expensive. You're constantly fixing something broken, or inventorying things that need to be fixed, or runnign to the store to get things that have run out or need to be replaced.

The views are amazing...the lifestyle less clock driven....the camaraderie can be amazing...and many of us wouldn't do anything else.

But know what you're getting into. Its a harder life than living cheap ashore.
 
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