Top 5 Lessons Learned Sailing 18,500 miles

Readers of the SailingBritican.com blog often send us questions and a popular one is, ‘What are your top lessons learned sailing?’ Within this article and video, Simon and I discuss five biggies.

This ‘Questions Answered,’ style article and video is a series of other common questions answered. Make sure to also read/watch:
– How did you get into sailing? (Q&A Video 1)
– Why we sold up and sailed away? (Q&A Video 2)
– What it’s like voyaging with kids – homeschooling? (Q&A Video 3)
– How we sold up and sailed away? (Q&A Video 4)

So, what are our five lessons learned sailing 18,500 miles?

Watch the video and then for more information and stories read the below article.

Lessons Learned Sailing Video


Lesson #1: It’s okay to make mistakes. In fact, it’s best to get comfortable making them.

If you can’t get over making mistakes you’ll find boating very difficult. We’ve met so many would-be-boaters that took their boat out once or twice only to quit boating after a some small mishap.

Sure, it’s embarrassing hitting a dock, anchoring too close to another boat, hitting a boat, failing to understand how to tie your boat to a dock, running aground, motoring on the wrong side of a shipping channel and, and…

The issue is, however, the only boaters out there enjoying the rewards of boating are those that fall off their horse and get back on (over and over again).

It’s often said that you’re not a boater if you haven’t run aground at least once!

Simon and I have sailed well over 18,500…that figure is just what we’ve done in our current boat over the last three years. In that time we’ve messed up quite a bit. Fortunately all our mess-ups have mostly bruised our ego only.

My worst recollection is when we took our old boat, a Moody 345, into Cowes Yacht Haven in the Isle of White. Cowes is the European sailing mecca. I believe it’s where the World Cup started.

Anyhoo, imagine Simon and I motoring into a VERY busy marina that’s full. We managed to get the last spot. Instead of it being a slip, we were instructed to ‘raft’ onto another boat. I yelled out to Simon, ‘how the heck do we raft?’ I had no clue.

Simon entered the marina where there were gin palaces that seemed three stories high – all occupied by upper-class, wealthy, gin and tonic drinkers. The watchers proceeded to look down upon us as Simon navigated into a DEAD END.

We had to somehow manage to back the boat out of the area we went down. And as many Moody owners will attest, ‘Moody 346’s don’t go backwards!’ Well, Simon managed to go backwards and forwards to do a 251 point K-turn.

Back, forward, back, forward, back, forward…

…And with only 6” to spare in the front and back. It was NUTS. I stood on the bow of the boat holding the bow line thinking, ‘God, please get me out of here.’ I was event temped to just jump in the water and end life.

We got out of the situation but we were still in the fire.

Simon managed to get around the correct corner and thankfully at the very last minute someone walked along the jetty to grab my bow line. I was thinking that I’d have to jump off the bow somehow, not realizing that it’s okay to get on another person’s boat when rafting.

And to make the horrifying experience even worse, when all was said and done I realized the front of my skirt was tucked into my knickers. HOW EMBARRASSING!

I shook for a couple hours while drinking a bottle (not a glass!) of wine.

Anyway – these things happen. If you get too shaken up about it you won’t go out sailing…you’ll spend all the time dreaming, getting the boat and then the boat will end up sitting in the marina.

So, get used to making mistakes. Get used to having your ego bruised. It’s part of the game.


Lesson #2: Servicing and repairs are the norm – expect them!

Everyone and anyone will tell you that boats need constant servicing and repairs. It’s 100% true. Not a day goes by where our servicing and repair list gets smaller. Once one thing is fixed two other breaks.

If you are going to get into boating and have the expectation that the lifestyle requires continues fixing/servicing it will make your life much easier.

When we started out we thought that once we fixed X, Y and Z we’d then be able to ‘enjoy’ the boat. Well, we’re still fixing X, Y and Z and the rest of the whole darn alphabet! Simon and I, however, have learned to laugh about our issues now.

We expect things to break and we now enjoy just getting on with it and fixing things.


Lesson #3: Don’t ever commit yourself to being at a particular place at a set date/time.

When we first started sailing we’d tell friends and family that we’d be in Greece by June or France by September. Not once were we correct in our estimations.

A few times we were caught out and had to sail non-stop for days to make sure we’d be where we said we’d be. Each time we took risks by sailing through storms that we should have avoided.

Lesson learned. We no longer tell people we’ll be anywhere. If anyone wants to fly out to us they need to get in touch a week earlier and then fly to the closest airport. From the airport our friends then need to find a ferry to get to the closest town.

It takes us all day to go the tiniest distance. We’ve learned that people need to find a way to get to us AND when we have guests, if we can’t get them to the airport in time we’re not risking a situation where we’ll sail through a storm.

When sailing there is almost never any certainty. Plans change. The weather gets in the way. Things happen. We learned the hard way…perhaps you’ll take this lesson from us and remember the lesson 😉


Lesson #4: There’s ALWAYS someone around to help when you have a problem.

This lesson kind-of makes ‘Lesson #1: It’s okay to make mistakes?’ a bit easier. No matter what country we’re in and what our situation is, someone is always around to help when we need it.

When our engine cut out in the Solent (one of the busiest waterways in Europe) another boat towed us to a marina. When our generator wouldn’t start, countless engineers/boaters helped to get it started (for free). During the scary situation of getting our main sail stuck up, a boatload of newfound Italian friends borrowed a friends boat and came out to help us get it down. This list goes on and on…

And in turn, we also are there to help other boaters all the time. We’re often helping newbies enter and exit a marina slip, help with anchoring or mooring balls. Simon has been known to retrieve countless run-away fenders, kayaks, hats and occasionally a tender or two.

The sailing community is amazing. Sailors help sailors.

But what we’ve also learned is that everyone we come across is happy to help – sailors and land people (landies). We’ve had several situations where we couldn’t communicate in the local language but that never stopped locals from helping us with all sorts of issues.

By sailing around the world we’ve learned that, despite what the media has to say, people are actually very kind and very helpful.

So…yes, you’ll run into issues. Yes, it’s often embarrassing or difficult to deal with when there’s such uncertainty, HOWEVER, in the end you’ll often find a solution AND make a new friend.

If you’re interested in knowing more about the variety of situations and experiences we went through during our 18,500 miles, please read my book, ‘Changing Lifestyles: Trading in the rat race for a sail around the world.’


Lesson #5: People will tell you you’re crazy and that’s okay.

When we first told friends and family about our sailing around the world plans the majority told us we were nuts. Heck, the Daily Mail in Britian published a few stories about us being the most selfish parents in England.

Looking back, I often felt very hurt by not having support. Simon and I truly felt as if we were on our own. We easily could have broken down and listened to our friends/family and stayed on land but instead we covered our hurt feelings and plodded on.

Now, everyone thinks we made the right decision and I oven overhear friends/family say, ‘I supported them all along! I knew they’d make a success of it.’

People are funny. Anyway, we learned a good lesson. When you go out and do things that are different from the norm, people often react in not-so-supportive ways. But that’s okay ☺

So, there you have it! Our five lessons learned sailing 18,500 miles. What lessons have you learned? Please leave a comment below as we love to hear (and learn) from others too!

Lessons Learned Sailing

Lessons Learned Sailing