Taming Your Fantasy-Like Expectations for the Sailing Life
My adult son had agreed to crew for me as I set out on my inaugural cruising voyage some years ago, an ICW run that was to take me and my 1967 Rawson 30 cutter south to warmer climes. Early in the morning of our departure day I started Ave del Mar’s inboard Universal diesel, and as it warmed, I poured two shots of my best spirits into two small pewter glasses. I knew I had to make a ceremonial offering to Neptune to secure a smooth journey.
Neighbors from the marina came out to see us off. As they stood on the dock, I made my soon-to-become standard pre-departure speech. My son and I sent Neptune’s whiskey over the stern and into the waters of Back Creek and each drained the few remaining drops out of our glasses and into our mouths. We were about to be real sailors. We were underway.
About four hours later we limped back into the marina slip with a transmission that sounded like a can of rocks falling down a set of stairs. We were humbled and a bit frustrated but happy to have met adversity and to have dealt with it. It was a full month before the transmission was rebuilt and a departure was again on the books, this time minus the crew.
The second journey started with less ceremony. Neptune got his pre-departure offering (as always), but missing were all those marina neighbors waving and cheering and wishing me well. This was still my first departure if one considers that during the previous departure I didn’t actually depart. This was when my friend and mentor Chip gave me some of the best sailing advice I have ever received: “Wish them well, if they are there,” he said to me of the dock crowd. “Tell them you are headed for the Bahamas. Motor off around the bend and out of sight, drop the anchor, and go to bed. Leave the next day. Or the day after that. It’s hard enough without you carrying the hopes and expectations of strangers on top of your own.”
For many of us that initial undocking for a cruising journey arrives loaded with emotional baggage. You have worked so long on the plan and have prepared so diligently for your departure. Photos of boat life have taken over your Instagram and Facebook accounts. Your coworkers know what you’re doing and are excited that you have this amazing spirit of adventure, a joie de vivre that may be missing from their own lives. Marina neighbors know you’re leaving, too, and might wish that it could be them. You’re on a high. There’s a swagger in your step as you walk down the docks. Then you leave, and the storyline frays at its edges.
I’m not suggesting that the cruising life will make you miserable or that you shouldn’t try. Quite to the contrary. But I also remember a coworker of mine when I first bought Ave del Mar who asked me, “What if you hate it?” That question blew my mind. It’s a boat, not a life sentence. I could pause, turn around, quit, sell the boat, die at sea… any one of a number of options. In the end cruising is just a transient state of being, and nothing more. It is a single tile in the mosaic of my beautifully complex life.
It isn’t other people’s expectations or fears that will impact how you and the cruising life get along—it is you and how you choose to react to bad decisions, bad luck, and bad days. My Bahamas Cruising class at Cruisers University at the Annapolis Boat Shows starts with a short speech that may border on being almost sermon-like about how easy it can be to be miserable in the Bahamas. The message is basically that if you are headed to the islands to find happiness, please don’t go. If you are miserable here, you’ll be miserable there.
Maybe you’ll be miserable that the groceries are expensive. Maybe you’ll be mad at the mosquitoes or noseeums simply for existing (that’s not hard to do), or mad at the weather for thwarting your sailing plans. Maybe you ran aground on a sandbar because your partner read the charts wrong. Maybe the mail boat didn’t arrive, or the store doesn’t have potatoes or cheese. I could fill an entire magazine with anecdotes of cranky sailors being crushed not by adversity but by the weight of their own expectations.
So, get ahead of the curve. Expect engine problems and mosquitoes—maybe on the same day. Maybe even at the same time. Maybe your transmission will fail as mine did. Maybe the fantasy-like expectations of the people who aren’t going with you are their own to grapple with.
All the highs are out there, too, occupying the same space as the challenges. Maybe you just need to tell those folks you are headed to the Bahamas when you really plan to go around the bend and sleep off the departure-related stress for a couple of days to get your head right. If you don’t tell them, they’ll never know.
About the author: John Herlig lives aboard his 1967 Rawson cutter Ave Del Mar and teaches at Cruisers University. Find him on Substack @jherlig.
