The Cruising Life: Decisions and Doubts

A cruising sailor's course corrections will be alright in the end

Have you ever set off in a sailboat cruising for the Caribbean with a boat full of provisions only to realize that the schedule you’re on is totally wrong? Did it sting, even just a bit, to do the right thing and park your beloved vessel in a slip? Did it bring a tear to your eyes to walk away from her, even if it was only for a month or so?

cruising boat in slip
When the obligations on land have been met and you return to your cruising boat, where are you going to go?

When you gave all your perishables to strangers at the boatyard, did you feel like you were giving back, or did it feel like you were taking a step back? Do you think that nice sailor from New Jersey actually ate the green cabbage you gave him? Or was he simply too polite to say ‘no?’

When the NOAA buoy close to your boat at the mouth of the Rappahannock River clocked winds at 56 knots sustained with gusts up to 91, did you worry a little? Do you know how long it takes to get to the boat from where you are so that you can see if she’s okay? Are you sure you doubled all the dock lines before you left her there to fend for herself?

Did you have fun trying to figure out how to quasi-winterize your boat so that she wouldn’t sink? Did you find a solution that means she will still be mostly ready to go next month when you return? How did you ever figure out what to do or not do? Remember that moment when you decided that removing the end cap from the heat exchanger would let the raw water drain and eliminate the risk from freezing? Have you ever heard of anyone trying that before? How confident are you that it was the right thing to do?

What could go wrong with the boat while you’re away? Will the cockpit scuppers clog and be a problem if a cold front brings epic precipitation? How many wraps did you put on the jib, and how well did you tie off the furling line so you could be sure it wouldn’t let loose under load? 

When your obligations have been met and you return to the boat, where are you going to go? Is St. Martin still the goal, or should you consider a change? Would heading to the Virgin Islands be better? Have you considered Culebra? If you do change your plans, will you really be ready to give up all that potential easting so easily?

What part of all of this made you feel like a bluewater cruiser while you added logs to the fire at your sister’s house? Are you going to be out of rhythm again when you get back aboard? Have you paused to consider that February sailing might be more challenging than November sailing would have been? Will it all seem like it was worth it when you’re back on the boat? 

Have you ever scanned social media to stare at friends’ photos from warm tropical islands, while back on land you dig through boxes of old clothes looking for wool socks to squelch the cold that has crept into your toes and now refuses to leave? Have you caught yourself staring at your own sailing photos, convinced that if you try just a little harder, you can will yourself into remembering what warmth feels like?

How does it feel to check your friends’ trackers every morning to see where they are? Is it a bit of a farce when you log in to offer support, advice, or opinions? Are you maybe kind of phoning it in at this point?

How many of your followers think that right now you are basking in a sunny, tropical anchorage? Have all those other cruisers found the balance between sailing and life, or are they, too, mucking through and just doing their best? When you get back down south, how long will it take for the sunshine and blue waters of the Caribbean to scrub the last shard of doubt from your mind? 

But aren’t you also pretty sure it will be alright in the end? Was that ever really a question?

by John Herling

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