How to Help Solo Sailors Keep Their Sanity!

My noforeignland writing colleague Telicia Campain recently wrote an excellent article about how relationships are created and formed while cruising.  Sundowners, cockpit gatherings, beach cocktails, and chance meetings on shore are all common experiences. I’d like to add an element to consider in this discussion; How do solo sailors fit into this system?

I have no statistical data to support this next statement, but from my observations, the cruising community is likely broken down into a few key demographics that look something like this:

• The Cruising Couple – 60%
• The Cruising Family – 25%
• Solo Sailors – 10%
• Other – 5%

If this is even remotely accurate, 85% or more of us always have at least one person with whom to converse, discuss ideas with, or to turn to for comfort in awkward situations, including social settings.

My journey

I fit into the ‘Solo Sailor’ category. I left Ontario, Canada in September of 2025, and have cruised my 1978 Tartan 37, SV Unhurried, solo through the Erie Canal, Hudson River, down the East Coast of the US, and island-hopped in the Bahamas for a little over 3 months.  I’m writing this while sitting in the Turks and Caicos.

I don’t speak for all solo sailors, of course, but many of us are a little different. We have to be. I’ll come back to that in a minute.

A common mindset in the cruising community

A cruising friend recently said about cruising sailors:

“We live a totally different lifestyle than everyone else. All cruising sailors are, like, 60% crazy to start with, so we all have that in common!'”

I think he’s about right. We all have more in common with each other than most any group we might have been a part of during our time on land. This is what should, and usually does, make striking up a conversation with strangers relatively easy.

The Solo Sailor

Let’s get back to the Solo Sailor. Lots of us have ‘normal’, healthy relationships back on land – husbands or wives, girlfriends, partners, kids – that we’ve chosen to leave behind for whatever reason. We’ve got friends, co-workers, and all the other types of relationships that cruising couples and families do.

On the boat, though, we’re entirely alone most of the time. That requires a certain mindset. Higher than normal independence, responsibility, and often, some introversion.

This means a couple of things.

1) When we get to a harbor, anchorage, or event after a lengthy period of being alone, the solo sailor is often STARVING for some social interaction.

2) We’ve have been in isolation for sometimes days or weeks – I went through a 15-day stretch in the Abacos where I did not meet a single person, for example. The sense of relief I felt when I next met a cruising couple caught me a little off guard!

3) We may not be entirely comfortable in group social settings to begin with.

It can be hard to switch gears from being entirely alone into social mode. I can honestly say that the first time I went to the famous Chat-n-Chill beach in George Town, Exuma, I was already feeling overwhelmed by the sheer number of boats in the harbor, the organization of the Cruisers Net, and the variety of activities that were being enjoyed around me. I walked around the picnic tables and beach area, passed through the bar, and looked, in vain, for a familiar face.

In most cases, what I saw were groups of families and couples, engaged in conversation. I couldn’t quite work up the courage to plunk down in an empty seat at a table, and I ended up getting back in the dinghy and going back to the boat.

The social upside of sailing solo

Here’s the interesting part.  I believe that solo sailors actually have an advantage in this scenario, although many of us may not quite realize it.

All of us cruisers are out here, doing something amazing, each in our own way.  This lifestyle is challenging, has inherently more risk that most land-based lifestyles, and generates opportunities to create interesting stories.

The solo sailor is doing all that by themselves.  I have not yet met a cruiser who doesn’t automatically respect that, with some small level of awe or amazement.  Cruising couples frequently have questions about how I manage watches on long passages, or whether anchoring alone is more or less stressful than anchoring as a couple.  (HINT- no one is there to yell at me, when I inevitably screw something up!)

There’s the paradox.  In my experience, solo sailors are welcomed into most conversations with open arms, IF we can work up the courage to try.

Making connections as a solo sailor

As a solo sailor myself, my advice, and request to you is this:

For solo sailors

If you are a solo sailor who would like to be a part of more social interactions, but struggle to break the ice – know that you are a unique individual within this community, and the vast majority of cruisers will want to hear your story, and ask questions about how you manage your vessel alone.  Be prepared with a couple of quick anecdotes.  Boat cards are, of course, a huge asset.

For other cruisers

If you are one of the cruising majority – a couple, or a family, try to keep an eye open for the person who might be looking for an opening to join your conversation.  Key tips for spotting a solo sailor:  walking slowly, looking around subtly (different from the head swiveling of a guy who’s lost his wife at the beach!), and especially if you see that person multiple times in the same area, there’s a good chance they are seeking a social opportunity.  Nervously sipping a drink is another strong signal.

Create openings

It doesn’t take much to create an opening.

• Make eye contact, and shift over a few inches on the picnic bench; even if there is already ample room, this is a clearly welcoming gesture!
• If you’re standing in a loose circle, shift your feet in a way that turns your body to be more open.
• Smile, and say hello – I cannot tell you how powerful that simple action is. If someone says hello to me while I’m walking by, I will always stop and introduce myself.

Part of the community

For many, this article will read as nothing more than common sense, and something that they’re already doing. That’s great!

However, if one Solo Sailor reads this, and takes comfort from the fact that they are not the only one who has to challenge themselves to overcome some social hesitation, I’ll be happy with that.  If one person who is part of the social majority makes a special effort to watch for and include a Solo Sailor into a conversation, that’s a win, too.

As Andy reflected, many solo sailors have unique tales, so who’s the most memorable solo sailor you’ve met along the way? And if you are a solo sailor, how do you manage the social side of life aboard?