Goodbye Season: The Ebb and Flow of Cruising Friendships

What it Means to Say Goodbye to a Fellow Cruiser

Fall is Goodbye Season for cruising sailors, and I stink at goodbyes. I am the worst person to be writing about this because I am the perfect model of what not to do. I go completely overboard wanting to shower the departing crew with attention and wine and dinners and thoughtful little items. I stay up too late making care packages, having drinks, chatting into the wee hours. And then overtired and hungover, I tearfully blubber goodbye as they cast off. Oh, but it doesn’t end there. I then walk around for a couple of days all deflated and lonely, wondering when we will ever share a harbor again. 

Saying goodbye is an inevitable part of the cruising lifestyle
Saying goodbye is an inevitable part of the cruising lifestyle

Really, it’s pitiful.

Yet it’s part of this life afloat, a big part of it. Sailors sail around, they meet other sailors, become fast and deep friends, and then sail away. Maybe forever. The end. So why do we put ourselves through this? The answer of course is that the friendships are worth it.

The Chesapeake Bay in general, and Annapolis in particular, is the super highway for cruisers headed basically anywhere. To and from Maine, Bahamas, Europe, Canada, the Caribbean, Bermuda: somehow all watery paths lead through Annapolis. New friends, old friends, internet friends: they all end up coming our way at some point. 

As a liveaboard and former cruiser, I somehow end up connecting with so many of them. It’s not always a love match. Sometimes, I can tell we will just say “hi,” make small talk, and part ways. Other times I know they are just looking for a car to borrow that afternoon, or a clean place to wash clothes and have a shower. And sometimes, we just won’t click and that’s okay. It’s okay because it saves me another heartache. The best are the ones who come and instantly become like family. Or even if it’s a slow friendship, the “close” is closer than normal. 

Sorry landlubbers if you just don’t get it, but it’s a hard fact. People living and cruising on their boats form very quick, very tight bonds that most land folks just don’t experience. I think it may be because boat people need each other in very real ways that don’t exist on land, and we know that deep inside. When you are out there without 911, without a plumber, electrician, or marine chandlery, you better have good relations with your fellow sailor because they will be your only hope in a pinch. Likewise you will come to the rescue of your fellow sailor many times, too, sometimes literally rescuing or sometimes just having curry on hand while someone is mid-dinner prep. 

The connections that cruising sailors make are unique and often inexplicable
The connections that cruising sailors make are unique and often inexplicable

There are a few different types of goodbyes. There’s the last blow out, six wine bottles until 3 a.m. goodbye. And there is the carefully planned exit, “we have a schedule to keep but we hope to see you next season” goodbye. And there can also be the radio call in the morning saying “the wind was right and the tide was high,” and “sorry, but we just had to go while the going was good.” 

Sometimes we see them again and again. Sometimes a decade and thousands of miles under the keel pass, but it’s like no time passed at all. Sometimes we promise and promise to see each other again, and we’re still trying. And the worst ones are when you know it just won’t happen. Those words are not uttered of course. There’s the old “the world is round, and so we’ll always meet again” saying that sailors toss about. Inside you know it’s just a Facebook thing from now on.

While cruising sailors may never meet again face to face, the connections and memories often remain
While cruising sailors may never meet again face to face, the connections and memories often remain

Often I find myself meeting a new boating bestie who I just know would hit it off with another one from last year, or five years ago. It’s hard to play matchmaker among sea gypsies, when plans are written in the low tide sand and dictated by the wind. One dear cruising friend of mine and I are now separated by half a continent, but we talk regularly on Facebook. When we’re having a fabulous chat online, typing at gale force and wishing the conversation were real rather than virtual, we both immediately refer to “the island.” The Island is a mythical place we have in our hearts where all of our favorite boating friends live together, anchored out or settled on land. We are in no particular country, with no particular plan; the important thing is that we are all together in the same place, kids running on the beach, dinghies nestled side by side, drinks flowing, music playing, and conversation going as long as we want. And the best part about The Island is that there are never any goodbyes. 

Winnie the Pooh sums it up best when he supposedly says, “How lucky am I to have something that makes saying goodbye so hard.” It’s true. I may cry with each stern wake that points away from our boat and long for the ones who are so far over the horizon we may never meet again, but in the end amazing friendships are not a problem I can complain about. 

By Cindy Wallach

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