Jan 16, 2010

How To Go Cruising Now (a step by step guide)

Step by Step: From no experience, to crossing an ocean:

Even before you hit step one, I recommend you tell no one! In my experience, most people are terrified to pursue their own dreams. To make themselves feel better they will try to hold as many people back with them as they can

1. Get a book on sailing. I've listed some that I have found useful here.

Time frame for step 1: a weekend or two.

2. Get a small sailboat. 15 feet or less? It's up to you. You just need to get your feet wet. Learn the basics on a boat that doesn't cost a lot. A Sunfish is a very popular, fun boat to sail. Start looking here: Craigslist.com

Time frame for step two: One month.

3. Get a sail boat with a cabin. Twenty five or Thirty feet. The purpose of this boat is to take some longer trips. Learn how to anchor for the night. Learn how to sail all night. Learn what it is like to be on a small boat. Don't let the small size fool you. Many people have sailed around the world on boats less than 30 feet long. For example, The Contessa 26.

Time Frame for Step three: A year or more.

Step three is the last step. Sail the boat as far as you can, as long as you can. You will always want a larger boat, but keep in mind: The boat you have now, is the one you can cruise in now.

Buying a bigger boat means you need to save for it. Which means you cant go cruising in the boat you own now because you are busy working so you can buy the next boat!

For other opinions on this line of thinking, visit this forum: go small, go now.


  1. We waited 4 months for that come on MORE and did the cat go with the boat?

  2. Just curious, was there a person who inspired the term "walter"? If so, is he a jackass dock hand in charleston, sc?

  3. Yep, walter was a real person from Charleston. I don't know if he is a dock hand these days.

    One time we were coming back to the dock from sailing on a friends boat. it was late at night and dead calm. He wanted to try backing his boat into the slip.

    Walter was standing on the dock watching. We were a little off coming in, but we could have man handled her into the slip, so I tossed a line to walter. He threw it back at me with a string of curses - berating us like he was our father with bad language.

    The guy driving the boat lost confidence, and pulled his boat in bow first. It was pretty sad to see someones confidence get crushed like that.

    That is the only docking story I have about Walter.

  4. Nice guide, although mine is a little different. I have a young family coming with me:

    Step 1: Get a book or 10 on sailing
    Step 2: Work very hard for a year saving as you go
    Step 3: Go boat shopping
    Step 4: Dont just buy any boat, buy the one that feels right between 30 and 40 foot (whilst sticking to your budget)
    Step 5: Start refurbishing her
    Step 6: Take her for small trips to get used to handling her
    Step 7: Slowly make your trips longer and try and cover more miles
    Step 8: Move onboard
    Step 9: Travel the World!

    Its a 3 year plan, steps 5, 6, 7 and 8 can be done when most of the refurbishment is complete.

    Wish us luck!

  5. Best of luck Tony!!

    I think I should change the first step on my list to:

    1. Muster up the balls!

  6. My first visit: Great web-site, and I love what you are doing.
    As for these steps, one should really really focus on the small boat skills prior to buying or trying to cruise a larger boat. The skills learned through experience on small boats will be invaluable. Subscribe to Small Craft Advisor magazine, join a sailing club or take some on water classes, cruise in small boats and learn all you can about big boats before buying one. Incidentally, after small boat cruising you may never want the big boat. If you still do, I'm sure you will find yourself more prepared and experienced than most other cruisers. The skills aquired by experience on small sailboat are in my opinion, the most important ones to anyone intending on extensive cruising. Cheers.

  7. I'd add that small boats make you into a better sailor. Big boats are forgiving right up until the point where you find out you don't know what you are doing and make mistakes. Small boat will give you the instincts and confidence to dock up sail and all the boat handling tricks you need to know. Then move up to a bigger boat--but don't rush it. Finally, I made dozens of trips offshore as crew with experienced skippers before I began skippering boats myself. And coastal sailing is more dangerous than offshore sailing--always know exactly where you are or you could kill yourself on a reef. Even if you think you know where you are, verify it over and over again.

  8. i agree a small centerboard sailboat is far less forgiving than a larger boat. i spent many years owning 10-15 small boats, reading MANY blogs and cruising articles and finally moving up to a sanjuan 23. i was amazed at how easily it handled and performed and HOW MUCH MORE forgiving it was in comparison. My wife and myself spent about a year fixing up the $1000 sanjuan 23. took her for only one test run on a smaller lake then threw ourselves into a two week cruise on lake michigan. dont let the fact that its a inland lake fool you, lake michigan is one of the deadliest bodys of water in the world ( google it). but the years of small craft sailing made everything second nature, accept my wifes almost never ending sea-sickness. her having no big water experiance was our only hitch. but she did well until we were anchored at a wonderful beach when a storm blew up in a matter of 15 min. we borded the boat and headed out in 3-5s that turned into 8-10s right now. we spent 18 hrs in a hellish storm with winds recorded @80 plus mph in a boat with an 8' beam. but the boat did everything it was suppose to as did we. now i beleive my wife is ready for anything. so as said above get some knowledge and dont let anything but fear stop you. no one is ever really ready and crapy things WILL happen, but if you can deal with them you are as ready as you will ever be. hate to quote nike, but (just do it). sorry for the corny ending