So you want to be a sailing family

Are we cut out for this?

In our last blog post I talked a little about the fascinating phenomenon of cool things happening in those times when we don’t plan.  Often our most memorable experiences are surprises.  That’s serendipity.

But if you want to go sailing for a week in the Med and you don’t have a boat or know how to sail you’re going to have to plan.  Book a captain.  Secure a boat.  Get yourself to the marina.  Buy Gravol.  Maybe more Gravol.

You can’t plan awesome

A few things can happen when planning something that you hope will be an amazing experience for you and your family:

  1. It could be disappointing because the experience was not as advertised or your expectations were too high
  2. It could turn out pretty much exactly as you thought – which would also be disappointing in my opinion
  3. It could turn out better than expected which, by definition, requires you to leave room for the unexpected:  perhaps you spent time with some interesting people, experienced some pleasant surprises, or overcame challenges you didn’t think you could

A lot of the value of our experience hinges on what we do before the experience.  If you get your hopes up too high, you are bound to be disappointed.  If you plan every last detail of the event, there is no flexibility to pursue spontaneous opportunities.  If your mind is already made up, you’re less likely to listen to other people’s good ideas.

To put it another way: you can’t plan awesomeness.  The best you can do is to put yourself in situations where awesomeness can happen.

Testing the waters

For us, this charter was literally about testing the waters.  We liked the idea of “cruising” but had next to no real experience.  So, we were excited about sailing for a week, but also very open to the possibility that it might just expose us as unrealistic land-loving dreamers.  The kids might fight all the time, some could get seasick, Linds might hate cooking in the small kitchen . . . all kinds of things could go wrong.  But, just like this trip, even if we learned it’s not for us, that’s a valuable lesson.  Like it or not, awesomeness and adversity travel the same highways and we were on the onramp.

We booked a charter with Jonathan Ross Sailing.  He answered a post Linds had put up on a Facebook group and we liked his style of communication.  He’s a professional one man show (plus his partner, Nathalie) with lots of experience and promised to have a 46′ catamaran ready for us in Mallorca for a week at the end of September.  I know a lot of you are curious about cost, so here it is:  we sent him $4500 and hoped he was legit (he is).

After a handful of emails back and forth to ensure things like passports, payments and provisioning would be taken care of, we met at the marina, made our introductions and boarded the 2006 Fountain Pajot Bahia 46.  The vessel was a little dated, according to Jonathan, but certainly seaworthy.

Our floating home

To us, she seemed like a lot of boat!  Four double cabins plus four more single beds in addition to four heads (bathrooms), not to mention the galley (kitchen), salon (table and seating), and all the exterior living space.  As Lindsay says, it was like a floating house.

We unpacked our things, had a little meeting about the rules of the boat, learned how to operate the heads and motored out of the marina as fast as we could to our first anchorage (anchoring is free, docking costs money).

A day in the (boat) life

Here is what an average day on the boat looked like:  Everyone woke up on their own time.  Some jumped in the water to wake up, others had a leisurely coffee and breakfast.  Half the day was usually spent snorkelling with schools of blue fish and exploring whatever cove or beach the kids called their backyard that day.  The other half of the day was spent sailing.  Some strong winds kicked up mid-week, but we stayed on the leeward side of Mallorca, so we could head out into them for some fun or tuck into bays for shelter.

The sailing was my favourite part.  Real sailors prefer monohulls over catamarans, but for me it was nothing short of thrilling to raise the sails and cruise at 8 – 9 knots in 25-30 knot winds.  We purposely took the boat out in the 1.5-2m swells – pretty big seas, according to our captain – to see if we could handle it.  We plotted a course, tacked and gybed, unfurled the headsail, took in a reef on the main . . . and sailed.  It’s hard to explain the serene, focused contentment that you feel when sailing.  It’s awesome.

We went through exactly zero Gravol.  In fact, everyone loved it including Lindsay (the closet thrill-seeker).

As for the kids . . .

As for the kids, they adapted to life aboard like it was second nature.  With no wifi or reliable power source on this boat, when they weren’t swimming, they commandeered the large table in the galley (since we ate at the outdoor table for every meal).  They drew pictures, learned how to solve the Rubik’s Cube, and played chess.

Their favourite game, however, was “All you can eat Cafe”.  One or two boys would run the restaurant and one or two would be customers.  The customers would order food that would then be built out of Plus Plus blocks (kind of like tiny Lego) and served.

At one point we heard Eli say how amazing the food was. Jake then replied, “Oh, I’m glad you like it, please give me 5 stars on TripAdvisor.”

Eli says, “I will and I will follow you on Instagram too!”

I guess we are officially a traveling family. These kids didn’t even know about TripAdvisor three months ago now it’s part of their every day lexicon.

Back on land

There is a lot to learn about sailing and we appreciated how keen Jonathan was to teach us every single day.  One week isn’t enough to become a captain, but by the end of that week our knowledge level and confidence had increased by leaps and bounds.

Even more importantly we stepped back onto land at the end of the week with a conviction to one day become a sailing family.  We’re not finished with our land-based travel yet, but we can envision phase two of Big Family Small World being on a sailboat.  Perhaps in 6-12 months.

Not that we’re planning.


  1. Love, love, love! Congrats to the mighty Crew! So cool to see how your kids went back to “old fashioned” creative play. And I love the line “Like it or not, awesomeness and adversity travel the same highways and we were on the onramp.” Will try, try, try to heed your words as I obsessively plan. 😉

    P.S. We have our website name (though it’s not up yet):
    We were tempted to pick SmallFamilyBigWorld but didn’t want to be too unoriginal or steal your great ideas. 😉

    1. Truthfully, I’m writing about it because we’re trying to reconcile the planning vs. spontaneity thing ourselves! At our current lodgings we don’t have wifi (which is a bit of a shock to the system!) so we spent the afternoon at a restaurant trying to plan our next steps from this location. Stressful! I want to know that our choice of accommodation will be awesome and am very uncomfortable with the fact that I can’t. Also, a week ago we had a plan laid out based on cheap flights and now everything has changed – ugh! So, don’t get me wrong – we don’t have this all figured out.

      Myers on the Move – perfect!! We will be the first to subscribe and will anxiously await every post!

  2. I found your website through the world schoolers Facebook group. We also have four, ages 3-10. We are working towards long term sailing. What you guys are doing also looks awesome. I would recommend reading “Voyaging with kids” and following Sv totem on FB, family of five that just completed a ten year circumnavigation. They also offer affordable monthly coaching that let us ask questions that I haven’t found covered in books.

    I am looking forward to following your adventures and starting our own soon.

    1. Hi Carl! Great advice – we’ve been aware of Sailing Totem for quite a while now, read their blog, FB, the sit down they did with SV Delos a while back. They are the godparents of family cruising, for sure, and well-deserving of their excellent reputation. We are still happy backpacking – there is so much more inland to see! – but even now we are considering signing up for their consultancy/coaching program in anticipation of that lifestyle change in a year or so.

      When are you guys starting? Where? What kind of boat? So curious to hear more . . . if you have a blog send it along or feel free to send us an email at

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