Thursday, September 12, 2013


Annapolis, MD

Congratulations, you are embarking on a voyage that will have many adjectives attached to it: exhilarating, energizing, terrifying, confusing, exhausting, challenging, exquisite, joyful. Come back here a year from now and add a few more of your own.

As part of the Monkey's Fist topic "Advice for the Freshman Cruiser," you will get some great tips about anchoring, navigating, passages and marine heads, all valuable. So, instead of piling onto the teetering mound of things you think you should know, I thought I'd take a different tack.

  1. Trust yourself. You have great instincts. They've just been buried under a heavy coating of civilization. Listen to your body, that small voice in the back of your head, that intangible feeling in your gut. Nobody, no matter how long they've been sailing, is wiser than your own instinct. If it doesn't seem right, don't do it. Period. Just smile and wave as everyone else leaves the anchorage, pour yourself a big cup of coffee and enjoy the day.

  2. Listen respectfully. You will get tons of advice, most of it welcome and all of it well-meaning. Take it all in, then go below, just the two of you, and make your own decisions. Learning to be a good listener will serve you well in all aspects of cruising -- and life.

  3. Pay attention. Retrospect will always tell you there were signals. Be particularly on guard when you say, 'that's strange,' like when the engine makes an unusual noise, or when the boat ahead of you going out the inlet is being tossed around like a child's toy. Pay attention, process the info, act on it. Don't hesitate to hesitate. Slow down, stop, turn around, question, regroup.

  4. Be open. You are going to meet hundreds of kindred spirits and many of them will turn into lifelong friends. Engage. Ask people about their lives, their families, their boats, their stories. (See #2.) Be prepared to tell your own story over and over and over. (You'll be SO HAPPY next time you see an old friend who already knows your story.)

  5. Slow down. This was one of my hardest lessons in breaking away from land. I was all goal-oriented and get there, get there! Then I realized I was already there, and I wasn't enjoying it. Cruising has taught me to enjoy now, to stay where I am until it's not fun any more, then meander to the next spot, sometimes only five miles away. Read #3 again.

  6. Go alone. With 1 through 5 in mind, go it alone. It's important to make your own decisions, and learn your own lessons. Don't let other people's plans or decisions interfere with your experience. (This is SO difficult your first year.) Every boat and crew has its own strengths, limitations and comfort zone. Meet up with friends at the next stop or the next. Keep in touch. Have a blast. Just make your own decisions and movements.

  7. Embrace everything. This isn't going to be fun all the time. That pristine anchorage in turquoise water off a deserted island comes with a price. You'll have moments when you hate the boat, the ocean, the wind, the waves, your spouse, yourself and sometimes all at once. It's okay. It will pass -- and it will make a great story. 

  8. Savor it. You'll never have another first year of cruising, where everything is crackling with newness, where you learn something every waking moment (damn it!), where nature electrifies you with its beauty and its power, where you are over-prepared, over-stimulated, overwhelmed and overjoyed. You have done an amazing thing. You had a dream, and you made it happen. You are the elite -- when you leave the dock the first day, when you sail into your first foreign port, when you raise that brand new Q flag and even when you're yakking over the rail into the Gulf Stream. You are awesome. Enjoy every single second of it.




who are these people? me | chip | cara mia | our very long timeline


  1. What timely advice for us. We toss off the docklines, out of our slip, no more home for Dos Libras... October 1. GULP! We are so excited! I'll remember this post all year long.

    1. Fair winds to you! Can't wait to hear all about it!!!

  2. Beautifully written Tammy! I will be saving these points in my notepad and talking them over with my wife. We are in the process of buying our first sailboat (currently living aboard an old powerboat) and dreaming of the day when we will cast off our lines on our first major cruise. Really enjoying your blog and the openness with which you write!

    1. Hi Kevin! I'm so excited for you! Even the planning and dreaming are rewarding. You might enjoy my old blog about that phase @ At the time, I found it so frustrating that nobody logged the preparation mode.

      Thanks for reading. I look forward to hearing about your adventures. Please let us know if you have questions. We love to give dreamers a hand.

      Sail on,

    2. Thanks for your warm response Tammy! Will do. All the best to you and Chip! By the way, did you mention what your post Cara Mia adventure might look like yet?

    3. Hi Kevin, We have not yet announced our new adventure. Some hints soon .....

  3. Thank you! We're trying to get out there as soon as possible (even though we're just in year 1 of a 5-year plan to get out on the water). It's a lot of "hurry up and wait" right now, and this was all great to keep in mind.

    1. Congrats on making the plan Devon! You might want to look at my old blog It is the last two years of getting off of land, much harder than anyone realizes. Feel free to ask us questions and keep in touch!