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The Uncertain Cruiser

The Uncertain Cruiser

A practical guide to help the Uncertain Partner & Enthusiastic Partner explore the potential joys and pitfalls of cruising life • Dual track, one for each partner

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    • A practical guide to help the Uncertain Partner & Enthusiastic Partner explore the potential joys and pitfalls of cruising life
    • You are unsure if you have the skills necessary to cruise
    • You are unsure if you will enjoy life on the water
    • Or, as the Enthusiastic Partner, you dream of cruising while your partner is uncertain

This guide will help you untangle your uncertainty, make a plan to develop the skills you’ll need, and help you find fulfillment in the cruising lifestyle

  • Untangle Your Uncertainty

    You’ll be able to articulate to yourself (and your partner) your specific uncertainties.

  • Know What Questions to Ask

    You’ll know what questions to ask as you and your partner consider the decision to cruise.

  • Make a Skills Development Plan

    You’ll know how to bring your existing skills aboard and how to develop other skills.

  • Discover New Joy

    You’ll have new sources of joy and fulfillment to explore in the cruising life.

  • Support Your Uncertain Partner

    As the Enthusiastic Partner, you’ll have the tools to build your partner’s competence, confidence, and contentment.

“These courses broke everything down into steps I could actually follow.”

What We'll Cover in The Uncertain Cruiser

14 Modules – Dual Track • Last Updated:


  • The Uncertainties of the Decision to Cruise

    Naming the uncertainty and talking about the uncertainty

    Making the decision to cruise:  Go or No-Go?

    Considering alternatives to full-time cruising

  • Building Skills to Increase Confidence

    Transferrable and non-technical skills you can bring aboard

    Skills you can develop before you start to cruise

    Skills you can build even while landlocked

  • Enthusiastic Partner Track

    How to fuel your partner’s competence

    How to fuel your partner’s confidence

    How to fuel your partner’s contentment

Frequently Asked Questions

I haven’t heard of you. Are your courses legit?

100% yes. You may not have seen us on YouTube—but our team has nearly 100 years of combined cruising experience.

We’ve taught at Cruiser’s University, the American Sailing Association, and major boat shows. You’ll find our bylines in all the major cruising magazines, and we’ve been interviewed by The New York Times and The Weather Channel.

These courses aren’t just “what worked for us.” They’re built on years of teaching, writing, and helping thousands of cruisers solve real problems and live their dream.

No clickbait, no “everything is perfect,” and no constant disaster stories. Just a realistic, practical look at life aboard—so you can skip the trial and error and get to the good parts faster.

Can I take the course designed for my partner?

Yes! Each course was designed to be helpful for the relevant partner, but you are ncouraged to peruse the course and activities for your partner. There is no additional charge for you to take the partner course.

Are you going to push me to say “yes” to cruising?

No. This course is not going to push you to agree to go cruising with your Enthusiastic Partner.  The course will give you tools and techniques to work through your uncertainties so you can decide for yourself if cruising could be a good fit for you.  We will also offer alternatives to full-time “forever” cruising you and your partner may consider.

I’ve already started cruising and I am uncertain about this lifestyle. Is this course for me?

Yes! Most of the tools and techniques will be helpful even if you’ve already moved aboard.There is a module on coping with lingering uncertainty in the cruising lifestyle.

Is there a schedule? Do I need to show up at a certain time?

Nope! There’s no schedule, no set times, and nothing you have to “catch.” The course is entirely on-demand—just text and photos you can go through at your own pace, whenever it’s convenient for you.

How long will it take to complete the course?

Plan on about 4 hours for the Uncertain Partner to go through the full course and 2 hours for the Enthusiastic Partner. This course may involve a shift in mindset, so you’re encouraged to take the time to process the material and complete all of the activities.

Can I start the course right away? Can I wait?

Yes — your choice! You’ll get immediate access after purchase. Your login info will be emailed to you, so you can start whenever it’s convenient for you.

Is it okay if my spouse, partner, or crew goes through the material too?

Yes — we actually encourage it! If someone routinely boats with you, it's helpful for everyone to have the same understanding. We just ask that you don’t share access with others outside your boating team.

How long do I have access? Is this a subscription or will I have to pay again later?

You get lifetime access with a one-time purchase — no subscriptions, no recurring fees. That includes all future updates, too!

Is the course video-based?

No videos. The course is entirely text-based, with helpful photos throughout. That makes it easy to read, even with limited internet or noisy surroundings.

Do I need internet access to take the course?

Yes, but you don’t need high-speed or perfect service. Because the course is all text and photos (no video), it loads quickly even with spotty or low-bandwidth connections.

Can I do the course on my phone or tablet?

Absolutely. The course works on phones, tablets, and computers—use whichever device is most convenient for you.

What if I’m not happy with the course?

Every course is backed by our 90-day hassle-free refund policy. If it’s not right for you, we’ll give you your money back.

What if I have another question?

Just ask! I’m Carolyn Shearlock, founder of The Boat Galley, and I’d love to help. Whether you're unsure if a course is right for you or have a question we didn’t cover, feel free to email me directly. You won’t get a bot—you’ll get a real reply from someone who’s been there.

Meet Your Instructor:

Katherine González

Katherine was the epitome of an Uncertain Cruiser, having spent exactly 30 minutes on a boat before meeting Andrés who had a dream to sail the world.  Three years and many days of sailing courses later, Katherine and Andrés sailed 11,000 miles across the Pacific Ocean on a 34-foot boat. She wrote about the joys and trials of their adventure in her book
The Co-Captain’s Log.  She’s excited to help you navigate the journey to become a fulfilled and skilled partner. 

Why Choose Our Courses?

Practical and Proven
No fluff, no filler—just clear steps that work for real cruisers.

Learn Without Overwhelm
Breaks down big topics into easy-to-follow lessons you can actually absorb.

Fits Your Life
No schedule, no deadlines. Learn when it works for you.

Instant Lifetime Access
Start today. Come back anytime. Includes all future updates, free.

Incredible Value
All the insight of seminars or coaching—at a fraction of the cost.

Made by experienced cruisers, these courses are like having a trusted friend show you the ropes—so you can move forward with confidence.

Trusted by over 8,200 cruisers (and counting)

How It Works

Pick Your Course or the All Access Pass
Choose the topic you need—or get all 9 courses in one discounted bundle.

Start Learning Right Away
Log in immediately from your email.

Go at Your Own Pace
No schedules, no deadlines. Come back anytime, from anywhere.

Raved About By Cindy G. . . .

This course gave me the tools and words to be able to discuss my fears with my partner, and for him to understand why I was so nervous. Even better, it let us work towards some compromises and now, guess what? I love being on the boat -- my way!

Verified Purchaser, The Uncertain Cruiser

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Our Guarantee

At The Boat Galley, we have one mission: to help you cruise with confidence.

 

As liveaboard cruisers, we understand the challenges and questions that come with boat life. That’s why we create practical products and courses designed to tackle the same issues we’ve faced ourselves—making your life on the water easier, safer, and more enjoyable.

 

Try our products and courses for yourself. If they don’t make your boat life better, use our 90-day FREE no-hassle return guarantee.

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