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1. Determine where you are. This has an impact on requirements for boat registration, insurance, fire extinguishers, what PFDs you carry, possibly a license for the VHF, and possibly some sort of safe boating credential.
   
   
2. Make sure your boat won't sink on you. This means carefully checking all the thru-hulls to make sure they operate smoothly, are in good shape, and keeping them closed when not in use. It also means ensuring the automatic bilge pump is working, and that there's enough power to run it, either in the batteries or from shore.
   
   
3. Make sure your boat won't leave you stranded. Make sure the engine is in good shape and runs smoothly, make sure the steering cables look OK, check all the standing and running rigging, etc. Ideally the boat will have a binder documenting where everything is, when maintenance was performed, and also how old things are (e.g. your standing rigging probably has a service lifetime of 10-12 years).
   
   
4. Clean your boat. Seriously! Power wash it, sand it, paint it, polish it, whichever everything needs. Make it look like new. Not only will you feel better living on it and sailing it, but you'll get familiar with the state of everything and know what will be next up for maintenance or repair. Depending on how things are, set aside time regularly to clean or polish something at random. Ideally it's before things show wear; that's the best way to keep things that way.
   
   
5. Go over the electrical systems very carefully. Better, get a professional. You will want to know how much power you are likely to draw (think instruments, radar, refrigeration, radio, lights, water pumps, etc.) and make sure you have sufficient battery capacity, that the batteries are of the correct type and in good shape, and that the wiring done safely according to the proper standards (and ideally slightly over-spec'd; boats are no place for a fire). Finally, everything should be easy to follow and clearly labelled.
   
   
6. Ditto for the plumbing, etc. You'll need to determine your local pump-out facility, know how to check your holding tanks, etc.
   
   
7. Assuming you have a stove aboard, always switch it off at the solenoid, let the flame go out, and only then turn off the stove (again, fire bad!).
   
   
8. Learn how to use the VHF and what the local channels and rules are. Much is standardized, but some is local.
   
   Resources:
   
   

• Assuming it has a diesel, I'm told this is a very good resource: https://www.amazon.com/dp/0071475354
  
• For sailing, you probably want a copy of this: https://www.amazon.com/Annapolis-Book-Seamanship-Fourth/dp/1451650191
  
• Get a copy of the ColRegs and local rules. This covers the rules of the road as well as lighting and other requirements. For example, the USCG publishes the local and international ones side-by-side here: https://www.navcen.uscg.gov/index.php?pageName=NavRulesAmalgamated (by treaty, local rules will usually be similar to the international ColRegs).
  
• The RYA has a nice VHF textbook that covers DSC as well; it's mostly correct and the only items that might not apply are the UK-specific radio channels. The USCG radiotelephone handbook is also useful.
  
• Once you've sorted out the basics, the "Sailing Virgins" channel on Youtube isn't that bad; they have some nice (and concise!) videos on various techniques.

The Complete Sailor, by Seidman & Mulford.

I'm reading the second edition of the Slight / DK manual at present, and IMO it's quite poor. It features an incorrect theory of aerofoils [more], and the layout is a bit cluttered, but most importantly it's badly written. Sentences are poorly phrased, with repeated and redundant words, whole descriptions are a messy clusterfuck, and the author uses nautical words which it doesn't explain or define (and I'm sure at least once wasn't in the index).

I was impressed by The Complete Sailor when I read it, my first sailing book, but having read two more in the intervening weeks, my opinion has only hardened.

It is a beautifully and elegantly constructed work, and I say that not just because of Mulford's illustrations - he does deserve as much credit as Seidman - but also for the layout and the way topics are handled. Each page or pair of facing pages covers a single topic, and there's something particularly impressive in how it's explained in a way that the reader can understand - the book starts by talking about the wind, and thereafter every term or concept that is used to explain the current topic is one that has been explained already, previously in the book.

I really think that the authors deserve a lot of credit for how they lay a foundation of information and then build upon it - they make everything simple and logical, and any time you think "what does that mean?" you know that it's already been covered, and it's easy to flip back to the right section. The authors have taken a lot of information about a complicated subject, and made it really accessible.

The Complete Sailor also focuses more on the core concepts of sailing and seamanship than the other books do - they make more digressions about types of life preserver, wood vs GRP, details of yacht vs dinghy, and key dates in yachting history.

I haven't read Sailing for Dummies, but Herreshoff's Sailor's Handbook is pretty good, and I'd recommend anyone pick up a secondhand or remaindered copy to set alongside Complete Sailor. There's probably some stuff in the former that the latter skips.

The Dorling Kindersley book, though, just feels a bit like marketing-orientated writing - it's a thick book, full of high quality glossy photos and clean modern illustrations; it probably looks commanding in the store, and it'll probably be bought as a present by mothers and grandmas for teenagers who have developed an interest in the sport. Nevertheless, it's cluttered, hard to read and factually wrong.

I know that I could have expressed this comparison with more clarity, but it's late here, so I can only apologise.

Around the World in Wanderer III by Eric Hiscock is fantastic. If you're looking for a more instructional book I'd also advise Cruising Under Sail by the same author.

Hard to have any list about cruising without starting off without mentioning Slocum's Sailing Alone Around the World as he was the inspiration for many of the following authors. He fixed a wrecked hulk of a sloop in a field in CT that he was given for free (as a joke) then proceeded to sail alone around the world (as the title would lead you to believe). At the time everyone thought that it would be impossible and likely suicidal to try and sail a boat so small around the globe and he apparently caused quite a stir when he did.

Of course The Long Way by Bernard Moitessier is an absolute classic for sailing literature. His was an account of the Golden Globe non-stop solo circumnavigational race, so there's not really any island hopping or drinks in paradise, but his writing is amazing and really gets to the zen of being at sea. He also named his boat JOSHUA after Cpt. Slocum mentioned above.

Jack London loved to sail and had a ketch (I thought it was a schooner, and Amazon page says schooner, but looking on GIS looks more like a ketch) built and sailed around the South Pacific and wrote about it in The Cruise of the Snark. London has some really funny commentary in there and it's a hell of a good read.

Last, and most expensive, is South Sea Vagabonds by John Wray. This book has been out of print for a little while and apparently is in high demand by looking at the price now. The cheapest I've ever seen it is between $40 and $50. I got my copy from a seller on eBay that lived in New Zealand for about $25 USD but after shipping ended up being about $40 total. That said, it was worth every penny. John Wray got fired from his job for daydreaming about sailing all day and since he had nothing but time on his hands decided to make a boat. Found all his wood on beaches and used his friends sailboat to haul it back to a mill, used a motorcycle and trailer to haul it from the mill to his house, then built a sloop with no prior ship-building experience. He sailed it all around the South Seas on various adventures and, like London, is a great and humorous author. Keep an eye out on ebay and used book sites for this one at a decent price (or find a library to borrow it from) because I guarantee that it's worth the effort and cash.

If you're into tall ships I just finished The Peking Battles Cape Horn by Irving Johnson which was a quick but thoroughly entertaining read. I'm now working my way through Two Years Before the Mast which is an amazing insight into the life of the merchant marine in the early 19th century aboard a square rigger.

I've kind of amassed a library. I'm a rank amateur, but here's what I've found helpful in at least orienting myself so far (I'm still working my way through these on a "total readthrough" basis, but I've flipped through and skimmed all of them) in the order that you should probably read them. Also, I've spent the last six months skulking around every sailing forum on the Internet.

I've found the greatest barrier of sailing for someone trying to get into it for the first time is understanding the language, and the second greatest is understanding the mechanical workings of the rig and how it physically interacts with the wind. These books have been super helpful in that respect. I can't speak to how much in the way of practical skill they may have imparted, but I know infinitely more about the subject than I did a few months ago.

• The Complete Sailor, Second Edition (mentioned already)
  
• The Sailing Handbook
  
• Don Casey's Complete Illustrated Sailboat Maintenance Manual
  
• The Sailmaker's Apprentice
  
• The Complete Rigger's Apprentice
  
• The Gaff Rig Handbook
  
• Hand, Reef, and Steer
  
  Those last two are because I despearately want a Gaff rig. If you're not planning on ever dealing with a Gaffer, you don't need them at all. If you only want to buy one of the books on the list, make it The Complete Sailor.
  
  There's also a bunch of online resources, such as about.com's "how to sail a small sailboat" article and ESPECIALLY the boating section of Animated Knots which can teach you a ton of knots.
  
  Hope that helps!

Tightening your cunningham flattens your sail, and a very direct consequence of this shape is that it opens your leech. This is generally a Good Thing^tm when you are in very light wind conditions.

If you have leech tell tales, you can look at them to see how your air is flowing out of your sail.

In general, in very light wind conditions (meaning the wind is likely more laminar than turbulent), a very draughty sail will stall easier.

Obviously this is all subject to experimental assessment, but the take home message should be this:

• light wind = laminar flow = easier stall
  
• more draught = more power but easier to stall
  
  Your goal should be to maintain flow above all else, and vary the parameters in that enveloppe. So try adding draught (loosening your cunningham) until you see your leech tales starting to curl back...
  
  (wave conditions also come into play when you realize that bashing into chop will stall the sail)...
  
  
  ------------
  
  
  If you are really interested in the dynamics of how and why this happens, get a copy of Principles of Yacht design by Larsson and Eliasson, and look at the foils section for an excellent description of this. Also, you can look at NACA foil designs and how they work. It is very well explained in that book. You will be surprised how much information is actually codified proper in engineering/scientific terms (e.g. draught position on the sail)...
  
  PS. Sailing is a very dynamic field. You are best served by learning and understanding our current state of knowledge as opposed to taking blanket statements a-la "never do that".

That's a good starter list - if you like Slocum, then I have to throw in my next two fave 'around the world in a small boat books.


Around the World Singlehanded: Cruise of the Islander by Harry Pidgeon is great. He was also a photographer and took some nifty photos.

The Venturesome Voyages of Captain Voss by Captain J C Voss is also a lot of fun. His vessel was a sailboat made from decking over and rigging sail on a single log dugout canoe he bought from some Pacific NW native americans.

Flying Cloud: The True Story of America's Most Famous Clipper Ship and the Woman Who Guided Her is the story of the fastest clipper ship ever to sail the horn. A most amazing feat still not equaled (OK some catamaran managed to beat her time a few years back - but all it carried was a crew - Flying Cloud carried a full cargo and paid for herself several times over on the first voyage).

Blown Away is a somewhat more modern tale of a couple with kids who chuck it all and buy a boat. Pretty funny.

Flirting with Mermaids : The Unpredictable Life of a Sailboat Delivery Skipper is a fun read of misadventures at sea.

I'm sure you already are but if not, start keeping eyes on the local used boat market. Wait and watch then pick your pitch. If it's too good to be true, it probably is BUT there are motivated sellers. People buy 2nd boats before selling their current one all the time, people inherit boats they can't afford upkeep on, people leave them at boat yards. This is especially true for smaller and older boats where the annual storage and upkeep can exceed the value of the boat itself.

Set up a separate bank account and figure out your annual cost of ownership. Start getting used to setting that money aside automatically each month. It'll give you a head start on your sinking fund so any early upgrades or repairs don't sting as much.

I watched and saved for 3 years until I was able to make a late-season steal on a well cared for Cal 2-25. Owner bought it for 6k, was paying 3500 for a slip and 1600 for winter storage. He was asking 5k but I waited until late in the season and offered 3400 pointing out the fact that he's breaking even on asking price by avoiding the looking winter storage. We settled on 3800 and we took ownership with 2+ months of the sailing season left.

While you're preparing, read the following books:

• Buy, Outfit, Sail: How To Inexpensively and Safely Buy, Outfit, and Sail a Small Vessel Around the World https://www.amazon.com/dp/1456310038/ref=cm_sw_r_cp_apa_Hi8YzbQ3KFZYY
  
• Don Casey's Complete Illustrated Sailboat Maintenance Manual: Including Inspecting the Aging Sailboat, Sailboat Hull and Deck Repair, Sailboat Refinishing, Sailbo (International Marine-RMP) https://www.amazon.com/dp/0071462848/ref=cm_sw_r_cp_apa_lj8YzbYPNZDPR

Putting a bluebook value on boats is really difficult. The equipment and condition can vary so greatly from one boat to another that it would be impractical to group them all together.

In my experience, the best way to get a feel for the value of a boat is to look at a lot of boats. Check out many listings of boats that are in your target size/style, and go and check them out. Even take photos and make notes so it's easy to remember what features were with which boats. Eventually you will come across one that just seems to be a good value when compared to the others that you have seen. It's a bit more time consuming this way, but I feel that you'll get a better boat in the long run using this method.

The problem with surveys is that many surveyors just don't do a thorough job. I wouldn't pay for a survey for a boat until I was quite certain that it was a boat I was ready to purchase. And even still, for a boat of this price a survey may not be worth it. Grabbing a copy of This Old Boat by Don Casey may be worth far more to you than paying for a professional survey since you'll be able to use the information on many boats, and you'll learn a lot about your future boat in the process.

I know I'm not really giving you a solid answer but I'm not familiar with the market in Seattle, and as you've mentioned, location can make quite a difference in the listing/selling prices.

Good luck!

As the widely varying answers in this thread suggest, the size of the boat is far from the sole criterion you should be considering; people have traversed the oceans in rowboats. It's not comfortable, but it CAN be done.

Instead, you should ask yourself the question "What do I want to accomplish, and what are the options available to me within my budget?" The Pardeys circumnavigated in a 24-footer that I would find extremely cramped, but they were competent sailors, knew what they enjoyed, and they did a great job of it.

If you're thinking about production boats, this book would be a good place to get you started. In the end, it's a combination of factors having to do with you, the boat, and the way you intend to sail her.

This isn't an answer to your specific question, but maybe it's helpful: The Complete Sailor, 2nd Edition has good sections on leaving from and returning to moorings and docks. Understanding the strategy and practicing in a safe place seems like the best way to learn.

Caveat: I've never sailed before. I'm just preparing to learn.

I think this is possibly the best: The Complete Sailor. Cleanly written, beautifully illustrated, and I learn something new every time I open it.

Btw, professional lessons are a relatively new invention. People have been learning to sail from their friends and neighbors for thousands of years, and all of the sailors I know are happy to pass that knowledge along. You might be better off, and save a ton of money, by joining a sailing club. Plus that way once you have a boat you'll have a group of peers to crew with you, go on cruises together, etc.

Hey, congrats, you have a budget. The downside though is your budget is pretty small for a world cruiser. You're going to be limited to older boats in the 26-30ft range and even then you may need to save up some to equip some addons like a liferaft, windvane and maybe a SSB radio or something for weather.

A start would be here: http://www.atomvoyages.com/planning/good-old-boats-list.html

You can also start with this book: http://www.amazon.com/Twenty-Small-Sailboats-Take-Anywhere/dp/0939837323

I wouldn't start collecting equipment now. I'd be looking a good solid core boat that you like the layout on that fits your current budget with some money left over. I'd then start cruising more locally on it first and then add the gear you want and need on her for an ocean cruise. Basically shake her down and learn on her with smaller cruises, then work up to bigger ones.

But you want that good solid base of a boat first. Something you can really trust to keep you safe in bad weather and rough seas.

Another option would be to just crew on other people's boats who are cruising the world.

Check out a couple of books by Nigel Calder. I recommend starting with Nigel Calder's Cruising Handbook as it's a pretty good general overview of everything you need to know for cruising, then try Boatowner's Mechanical and Electrical Manual as a guide to all of the stuff that you will spend all of your free time fixing and maintaining. I also have Marine Diesel Engines. He does a great job of explaining everything you need to know in an accessible way. He manages to get to some pretty advanced skills without assuming very much previous knowledge.

I was pretty much you last summer. Land locked state, no sailing club close by, no relatives or friends who sail, and a burning desire to get out on the water.

I was able to learn to sail in four steps:

1. Read a beginners book on how to sail. The book I chose to read was The Complete Sailor by David Seidman. http://www.amazon.com/The-Complete-Sailor-Second-Edition/dp/0071749578 This was a fantastic book that was only $10 bucks for the pdf version. It is well written and contains some fantastic illustrations. Talks about everything from keeping a sailors eye on the wind and weather, to docking and anchoring, and even has a chapter on trailering your sailboat if I recall correctly. Also Inspecting the Aging Sailboat by Don Casey was a fantastic read to help a brand new buyer have some idea of what to watch out for and what questions to ask when buying a used boat. http://www.amazon.com/Inspecting-Sailboat-International-Marine-Library/dp/0071445455/ref=sr_1_1?s=books&ie=UTF8&qid=1449298309&sr=1-1&keywords=inspecting+the+aging+sailboat
   
   
2. Buy a small, cheap boat. I decided to start small and limited myself to getting a dinghy sailboat that was under a thousand dollars. I have heard that starting on a dinghy is ideal. Learning sailing theory in small, responsive craft will help you when/if you move up to larger keel boats where it isn't as obvious that you are making small mistakes. A thousand dollars is easy to make at a summer job. The repairs on small boats are really cheap and if things break your not usually out much money. You will learn the fundamentals in an environment where mistakes like bumping into the dock are not overly disastrous.
   
   
3. Watch YouTube videos. I ended up purchasing a Hobie 16 after reading the books. I had the gentleman I purchased it from help me step the mast and raise the main before I finally bought the boat. No test sail, just did it right there in his front yard. Most people will be more than happy to help you rig it up the first time if you just ask. Afterwards I hit Youtube and watched videos on how to rig the boat to make sure I had it right. Searched for more videos about "How to sail a Hobie 16" and watched all the videos I could find.
   
   
4. Practice, practice, practice. After I had watched several videos, read the books, and set the sails up in the yard it was time to get out on the water. I literally just picked a day with 2-3 mph of wind, put the boat in the water and went for it. Once I was actually out and sailing, the details worked themselves out. I watched even more videos and asked Reddit the occasional question.
   
   I was able to go from no sailing experience to flying hulls in 20~ mph wind inside of a summer with this method. https://www.youtube.com/watch?v=c105II-L8OA Far from perfect, but we are having a blast. I think a teenager would be able to pull of a similar feat with no problems. You will find fumbling around on the water is far better than dreaming from the shore.
   
   
   
   
   

Hey friend. Pilot/Sailor here. There are parallels between aviation and sailing..absolutely, but my advice would be to approach sailing with the same independence with which you approached flying, initially.

There is an ENORMOUS body of information for potential "cruisers" available on line, luckily. I recommend that you hit the forums on Sailnet.com, for starters.

Boat-length isn't really the driving force behind your decision, so much as stability and ease of handling. Ease into the information you read through, and disseminate thusly which sort of cruiser you aspire to be. There are TONS of options.

Bluewaterboats.org
& this (basically a rod machado's take on sailing.)

I think you're getting a lot of good advice because

1. You've identified your needs and background
   
   
2. You've pointed out a bunch of specific boats you're thinking about.
   
   In addition to what's already been said on this thread, I'll point out a book I try and always recommend highly to folks looking at buying older sailboats. It'll really help you zero in on what to look for as you're sizing up older boats in terms of condition.
   
   https://www.amazon.com/Inspecting-Sailboat-International-Marine-Library/dp/0071445455
   
   The other thing to realize is that there absolutely no need to be in any kind of hurry. Buy in haste, repent at leisure. It's ALWAYS a buyer's market for old 70s vintage 30footish sailboats. Even if any of these gets snapped up, another one will come along.
   
   EDIT: one more thing. Do consider where the boat is currently moored, and find out if you can transfer the slip to your name. Finding a place to keep a boat can be a hassle. And if it's already in a good location for you, that can be a plus and can save you some work once you own the boat. I wouldn't make that the overriding concern. But could definitely be a tie-breaker between otherwise comparable boats.
   

http://www.amazon.com/Fast-Track-Sailing-Learn-Three/dp/0071615199/ref=wl_it_dp_o_pC_nS_nC?ie=UTF8&colid=1J4DZ3N7YF0RQ&coliid=I2B25B3Z0DNFA9

http://www.amazon.com/Annapolis-Book-Seamanship-Edition-Revised/dp/0684854201/ref=sr_1_1?ie=UTF8&qid=1345094921&sr=8-1&keywords=Annapolis+seamanship

As former instructor and 45+ years of sailing...2 good books for beginners. Colgate's Fast Track gives a very concise, clearly written 3 day program. A better 3 day jump start than any other I've found. Focuses on the core skillset to survive your first few missions. The Annapolis book is your in-depth comprehensive reference for all sailing related subjects. Way to thick to read straight through. Use it like an encyclopedia.

Knot books:
This book is great for the basic, every day kind of knots. I'd suggest this one to get the basics down.
If you have a lot of time/money/desire to learn knots, this is the knot bible. It is awesome. I found a used copy in good condition for cheap, so if you have a used bookstore, I'd suggest poking around in there for a copy. This book is HUGE (600+ pages) and incredible. However, it is somewhat excessive, with a lot of knots you'll probably never use.
As for sailing books, I like this one for explaining the basics. It not only explains how to do certain maneuvers, but why. The example on proas tacking is one of my favorites.

I know you said books are not right because of time, but I still want to highly recommend The Complete Sailor, Second Edition.

Amazing intro book on sailing. Amazon Prime in just a few days if you can wait that long!

I like that mug! Great handle.

I didn't include a link to the book because there are so many re-printings. I've got a nice hardcover that also could make a good coffee table book. This is it. Had to go find it, again.

I would second the Kon-tiki reccommendation.

I would also highly recommend Bernard Moitessier's "The Long Way"

Mainly for his passages about nature, the sea, and his views of humanity. He was a pretty quirky french guy who grew up in Vietnam, but it struck me as some of the best writing in that vein by a sailor.

>"I am a citizen of the most beautiful nation on earth. A nation whose laws are harsh yet simple, a nation that never cheats, which is immense and without borders, where life is lived in the present. In this limitless nation, this nation of wind, light, and peace, there is no other ruler besides the sea."

and

>"You do not ask a tame seagull why it needs to disappear from time to time toward the open sea. It goes, that's all."

Seem to be very in line with what you're writing about.

Your local power squadrons are a great idea if you're planning on larger cruising boats. But they do mostly course work classes for people who own their own boats or are planning on buying their own cruising boats.

Dinghy sailing just drop by your local dinghy sailing centre and ask them what their lessons start for.

The best book that I've ever found for learning how to sail is the following: http://www.amazon.com/Royces-Sailing-Illustrated-Patrick-Royce/dp/0894716964/ref=sr_1_1?ie=UTF8&qid=1374379136&sr=8-1&keywords=royce%27s+sailing+illustrated

The best way to learn is to get out on the water though. Whatever avenue you take it should involve actually getting out there.

I'm in the same spot for dreaming about sail cruising after the kids move out. I really enjoy listing to the podcasts on https://www.59-north.com/ and really want to sign up for an ocean passage with the company. Meanwhile I'm studying the The Annapolis Book of Seamanship and following a couple of folks on youtube like https://www.youtube.com/user/drakeParagon. With all my armchair browsing on Yachtworld I'm always searching in the 20'-30' foot range for affordable daydreaming. A rule of thumb I've heard is to have triple the boat price saved up. I like the saying I've heard of "Go Small, Go Simple & Go Now"

If you pull that off shoot me a message and I will email him all the pictures. Another thing I will suggest is a book called "This Old Boat" http://www.amazon.com/This-Old-Boat-Second-Completely/dp/0071477942 I have the first ed. but I am sure its all still there. It is a great reference on restoring all kinds of boats but especially older smaller sailboats.

I charter right now, OCSC is A-B-C docks. I don't know anyone who knows diesels, sorry. But I have worked on motorcycle engines (never cracked the case open, though). Between that, whatever you know, and this, you might be in good shape. I'm willing to give it a go if you are, anyway.

Best of luck!

If it helps, here were my requirements when selecting one, in no order:

• Folding, for convenience;
  
• Secure lock for the blade;
  
• Easy one-handed opening. None of those little fingernail slot things;
  
• Blade approximately 3" long. Much less and it isn't useful; much more and it's considered a weapon in some places;
  
• Blade part straight and part serrated, for versatility;
  
• Marlinspike;
  
• Good value / relatively inexpensive. I can't spend my hard-earned money on a mother-of-pearl inlay or whatever, though spending extra for quality construction, good steel, etc. is worth it;
  
• Rugged construction, as I need to be able to trust my core gear without question;
  
• Lanyard loop placed where I can open either the blade or the spike and use them naturally without interference from the lanyard;
  
  Based on this, I selected the the Myerchin P300. I've used it for about four years now, sailing 100 to 130 days per year. This thing is rugged and well built. The pliers seemed like a gimmick at first but I have used them so many times, usually when I don't expect to need them (otherwise I would be carrying the right pliers for the job), and they're just the right size for a lot of tasks.
  
  The Boye is my second choice, but at over four times the price I think I would be kicking myself if I lost it or saw it washed overboard.
  
  My third choice is the Camillus rigging knife. The construction just doesn't feel as rugged to me as the Myerchin, though I haven't really given it a fair shake.

Sensible Cruising is both incredibly practical and timelessly wise. Don Casey, one of the authors, has written some of the best manuals on sailboat maintenance and repair in existence. If you want to extend your cruise, this is your book

What did they re-core the decks with? Older boats are cheaper then newer boats. This doesn't necessarily equate to problems but if everything seems in fair shape, you could look into a survey to make sure it all checks out. The main issues from older boats is rot, either the core or interior's. LifeCaulk (which is what was used on most all of the hardware) has a lifespan of 10 Years, max. They used to claim it was good for the life of the boat, and a lot of people never took up the hardware to rebed it. Causing leaks. The windows/portholes also are something to look at for leaks.

You should probably pick up this book, https://amzn.com/0071445455 read it over and as always with a large investment get it survey'd.

Oh wow, I have not read that one - I'll have to get a copy.

I've gotten much enjoyment out of reading Royce's Sailing Illustrated, Capable Cruiser by Lin & Larry Pardey [along with everything else by them], and the Annapolis Book of Seamanship, among others.

The Complete Sailor is an awesome book - use the Look Inside feature to check out the illustrations - they give the book a lot of character so it's great for a coffee table or for casual reading. Might be a little too novice for a 1-year sailor, unless your dad hasn't had much formal instruction.

As mentioned already, Chapman's is good - it's the bible for any waterman. However, it has so much stuff there's very little on sailing (only 40 pages on the topic). It won't tell you much about sail trim, for example. But it covers a lot - I read it cover to cover last year and if I retained anything (I didn't) I'd be a damn genius.

I can't wait for The Annapolis Book of Seamanship to come out with it's much needed 4th edition in January. I hear this is the bible for sailors, but I haven't picked it up since I'm waiting for that new edition. But only because it has more electronics/GPS mentions - I'm sure all the actual sailing stuff is the same between the two.

Haha! Around really hard core racers I feel that way all the time still. I just shut my mouth and nod sometimes. Being immersed in a new language helps some.

I found this book to be particularly helpful.

Highly highly recommend The Complete Sailor by David Seidman. Not sure why but I find myself reading and re-reading this one more than Chapman (which is another must have). Happy hunting!

The Complete Sailor, Second Edition, by David Seidman is the best beginner book I have found. It covers a lot of ground and is very clear in what it covers.

Once you've read Slocum's book, check out The Long Way, By Bernard Moitessier.

Some other books I highly recommend, especially if you're setting out alone

• [One Hand For Yourself, One For The Ship, by Tristan Jones] (http://www.amazon.com/One-Hand-Yourself-Ship-Essentials/dp/0924486031/ref=sr_1_1?s=books&ie=UTF8&qid=1345689272&sr=1-1&keywords=one+hand+for+yourself) sexy title!
  
  
• What Shape Is She In Seriously, get this book and take it with you when you start looking at getting a boat.
  
  
• Celestial Navigation for Yachtsmen Forget your gps, get a sextant and do it for real.

I've read a lot of sailing books. Slocum is good, but it can feel a bit archaic at times. In my opinion the book that truly captures the spirit of sailing is http://www.amazon.com/The-Long-Way-Bernard-Moitessier/dp/0924486848 - It's the closest thing to a bible I'll ever own.

I have enjoyed these:

https://www.amazon.com/gp/product/0756689694/
https://www.amazon.com/gp/product/0071350993/

Edit 1 to add: Also, for entertaining reading, Joshua Slocum's book and Voyage for Madmen

Definitely. You'll save A LOT of pennies too, more than you could possibly imagine right now.

One option if you want to get going sooner is to buy an engineless beater, and Don Casey's book, and get going: http://www.amazon.com/Caseys-Complete-Illustrated-Sailboat-Maintenance/dp/0071462848/ref=tmm_hrd_title_0?ie=UTF8&qid=1370306245&sr=8-1

https://www.amazon.com/Boatowners-Mechanical-Electrical-Manual-Essential/dp/0071432388 This will help you fix nearly everything. It's slightly technical but has very good information.

Best investment you can make! Everyone should have this on their boat! http://www.amazon.com/gp/aw/d/0071432388?pc_redir=1397569458&robot_redir=1

Cap'n Fatty has at least one book that addresses this question. He would add a #4 to your list, "You live frugally while at sea." But he also mentions a pretty good list of "jobs you can do at sea" - including skills in demand among other boat folks. He even mentions a dentist who had an exam chair in one of the cabins on his boat, IIRC.

I've had people here recommend me some good books on this topic:

Inspecting the Aging Sailboat - Don Casey

For fiberglass specifically:
Surveying Fiberglass Sailboats - Henry C. Mustin

Buy this book, it's great!

Don Casey's Complete Illustrated Sailboat Maintenance Manual: Including Inspecting the Aging Sailboat, Sailboat Hull and Deck Repair, Sailboat Refinishing, Sailbo https://www.amazon.com/dp/0071462848/ref=cm_sw_r_cp_api_tiBTybADK132Z

This is a great reference! https://www.amazon.com/gp/offer-listing/0071477942/ref=sr_1_4_olp?ie=UTF8&qid=1506370390&sr=8-4&keywords=don+casey

I have a copy of that book - I don't remember it as being very good.

David Seidman's The Complete Sailor - it's so good that it defies words; it's hard to explain how clear and well-structured it is.

Twenty Small Sailboats to Take You Anywhere
https://www.amazon.com/dp/0939837323/ref=cm_sw_r_cp_apa_i_CAPWCb34QV9EG

These will be more in the civic line, although in terms of good little work horses, they can usually still play.

I have this guy, I really like it. Small and good for unjamming ropes and cutting them if you need to in a hurry

http://www.amazon.com/Camillus-Carbonitride-Titanium-Folding-6-5-Inch/dp/B005LHGBB4/

In addition to the other great advice, I'd suggest reading The Complete Sailor, and to emphasize, sail as much as you can.

So, coastal cruiser, homebase Maine, 'Snowbird' itinerary.

That leaves the budget question as the big variable we need if you want specific recommendations. You can do this at many different $$$ levels...but the boat selection and priorities will change.

This is a good place to start: Greg Nestor - "Twenty affordable sailboats to take you anywhere"

http://www.amazon.com/Twenty-Affordable-Sailboats-Anywhere-ebook/dp/B00422LH04/ref=sr_1_1?s=books&ie=UTF8&qid=1368355828&sr=1-1&keywords=Nestor+sail

If you need to go for less $$$...that means either smaller, older, or more 'sweat equity' by you. Don't give up here. Many sailors have years of fullfilling cruising under the 'go small, go simple, go early' approach. Refer to this very similar book by John Vigor - "Twenty small sailboats to take you anywhere"

http://www.amazon.com/Twenty-Small-Sailboats-Take-Anywhere/dp/0939837323/ref=sr_1_cc_2?s=aps&ie=UTF8&qid=1368355337&sr=1-2-catcorr&keywords=Vigor+sail

Plan on 50% of purchase cost, additional, to put it right, depending on the boat and your plans. Strongly consider a survey for the boat that is the "one". They cost too damn much to do more than one, but can save you from that BIG mistake.

The three books about the first Golden Globe solo round the world race:

• The Long Way by Bernard Moitessier
  
• World of My Own by Robin Knox-Johnston
  
• The Strange Last Voyage of Donald Crowhurst by Nicholas Tomalin and Ron Hall
  
  The first two are autobiographical. All three are great reads about the first solo round the world race.

oh..shameless plug for one of my heroes.

​

https://www.amazon.com/Buy-Outfit-Sail-Inexpensively-Safely/dp/1456310038/ref=sr_1_1?ie=UTF8&qid=1537972806&sr=8-1&keywords=goodlander

I taught myself to sail with this book.

http://www.amazon.com/dp/0684854201

Read it, bought a boat, and started practicing. Have fun!

THIS:

>Once you've read Slocum's book, check out The Long Way, By Bernard Moitessier.

He was fascinating.

Start with the classic, "Sailing Alone around the World", by Joshua Slocum. I would also recommend some other older accounts, such as Cruising under Sail, by Eric and Susan Hiscock.

Get to know Lin and Larry Pardey and their books.

For specific advice on boat systems, see Nigel Calder's books Nigel is a very clear and detailed writer.

Work random jobs at hotels when your in port for a month or so. Looks like he's a freelance photographer as well. Probably runs a website too. The most expensive part is getting the boat.

Edit: Awesome book on the subject

http://www.amazon.com/Inspecting-Sailboat-International-Marine-Library/dp/0071445455

This book is pretty something you may need to look at.

Regarding financial stuff, this is very good:

http://www.amazon.com/Voyaging-Small-Income-2nd-Edition/dp/1888671378

Some good reading:

http://www.amazon.com/Cape-Horn-Starboard-John-Kretschmer/dp/1580801625/

http://www.amazon.com/World-My-Own-non-stop-voyage/dp/0713668997/

http://www.amazon.com/Sailing-Alone-Around-Joshua-Slocum/dp/0486203263/

http://www.amazon.com/The-Long-Way-Bernard-Moitessier/dp/0924486848/

http://www.amazon.com/Across-Islands-Oceans-Journey-Around/dp/1470004615/

http://www.amazon.com/Voyages-Extraordinary-Times-Larry-Pardey/dp/1929214987/

Is this it? I'm thinking of getting it and want to make sure.

I've got the Sailing Bible. I hear the Annapolis Book of Seamanship is a must have as well.

If you have a boat you need to get "Don Casey's: This old boat" It will explain this repair as well as all other you might need.

John Vigors 20 small sailboats to take you anywhere:

https://www.amazon.com/Twenty-Small-Sailboats-Take-Anywhere/dp/0939837323/ref=sr_1_1?ie=UTF8&qid=1499492768&sr=8-1&keywords=20+small+sailboats+to+take+you+anywhere

Go get yourself a copy of "This old boat" by Don Casey. They should be widely available secondhand.

He recommends installing a second maintenance bilge pump with a smaller hose, which mops up whatever the big one lets back down again when it turns off the power.

I agree it’s not a reputable blue water boat, but the Catalina 27 is listed in Twenty Small Sailboats to Take You Anywhere because many people have crossed oceans in it.

https://www.animatedknots.com/boating-knots

​

In addition to showing how to tie the knots, there is a lot of information about when and when not to use each knot.

​

And, unlike The Ashley Book of Knots, there is a reasonable number of knots.

​

Animated Knots would suggest that the halyard hitch might be what you are looking for,

​

https://www.animatedknots.com/halyard-hitch-knot

Buy a book!

Inspecting the Aging Sailboat (The International Marine Sailboat Library). https://www.amazon.co.uk/dp/0071445455/ref=cm_sw_r_cp_apa_i_cbDqDb8T5QNS7

http://www.amazon.com/This-Old-Boat-Second-Edition/dp/0071477942

this is the book you are looking for

For all knots and uses there is a book called Ashley's book of knot's it has all the knots you need to know and more

Link to the book: https://www.amazon.com/Ashley-Book-Knots-Clifford-W/dp/0385040253

The Annapolis Book of Seamanship

http://www.amazon.com/Annapolis-Book-Seamanship-3rd-Revised/dp/0684854201

The book “the long way” is a must read for sailors

https://www.amazon.com/Long-Way-Bernard-Moitessier/dp/0924486848/ref=nodl_

Go to your local library and check out any books they have on the subject. I found that my library has books for sailing in two different Dewey decimal system locations so check them both out.

The two big ones that I hear people recommending all the time are these two:

http://www.amazon.com/Chapman-Piloting-Seamanship-Edition-Handling/dp/1588169618/ref=sr_1_1?ie=UTF8&qid=1380854381&sr=8-1&keywords=chapmans+piloting+and+seamanship

and

http://www.amazon.com/The-Annapolis-Book-Seamanship-Edition/dp/1451650191/ref=sr_1_2?ie=UTF8&qid=1380854397&sr=8-2&keywords=anapolis+book+of+seamanship

Although that second one doesn't come out with the revised version until january. (The last update was 1999)

[Dove] (https://www.amazon.com/Sailing-Alone-Around-Joshua-Slocum/dp/0486203263)


[Sailing Alone Around The World] (https://www.amazon.com/Sailing-Alone-Around-Joshua-Slocum/dp/0486203263)

[The Long Way] (https://www.amazon.com/gp/aw/d/0924486848/ref=mp_s_a_1_1?ie=UTF8&qid=1496093457&sr=8-1&pi=AC_SX236_SY340_QL65&keywords=the+long+way+sailing&dpPl=1&dpID=51L%2Btgd-fQL&ref=plSrch)