Why Isn't Cruising ALWAYS Fun?

After we released our last video, #119, 5 Bays in 5 Days, it got me thinking about what led us to this life. Like most people who chuck everything to dive into the cruising life full time aboard a sailboat, we had gotten a taste of it that led us to not only want more, but to get the whole enchilada. That could come in many forms, like a week visiting someone else who owns a big cruising boat somewhere on a coastline with infinite sightlines to the horizon, or having a smaller boat that you decide to take "camping" for the weekend at your local lake. For us it was both of those things...the latter for many years...but more so it was chartering a big boat in the Caribbean.


I had done it several times before meeting Loren, then we had the most memorable charter vacation of them all...the one on which we got married. It was the British Virgin Islands and it was an idyllic week, not only for a wedding, but for sailing in general. Joined by some close friends and family (one of which got his credentials on line in order to marry us), we sailed for just a couple days before landing at our wedding site of Marina Cay, formerly the site of a small open air hotel and a Pusser's restaurant. The wedding was too perfect and too full of storied to tell briefly enough here (maybe a later post), but it was also followed by a perfect week of cruising the BVI, like most weeks of cruising the BVI are. We swam, we drank, we ate out, we ate big on the boat as well, we sailed, and we repeated until we had to turn the boat back in.


With experiences like that, who wouldn't want to do it full time? But we're also not naive...well, not THAT naive, and we knew the cruising life wouldn't exactly resemble a cruising vacation. And it doesn't. Or at least it barely does. And I think this is what stops many cruising dreams short. Most people aren't naive enough to expect living on a boat to be one big endless sun-drenched, floating party. But I think most expect at least a little more of that aspect than they get.


Once you're living on a boat full time, especially if you aren't retired or already independently wealthy, you still have to work for a living. And in most situations, trying to do that aboard a rocking boat, in close proximity to your cruising mates, with sketchy internet, sometimes oppressive temperatures, and other detachments from the creature comforts we've all become accustomed to can be extremely challenging no matter your line of work. Add in for me the need for extreme quiet and we have additional stressors on me, Loren, and Rivers. You also have a boat to take care of if you want it to take care of you. Diesel to burn, water to make or procure, power to generate, numerous systems that require your daily attention to keep them functioning...things you give barely a first thought while chartering.


Another factor that surprises many is the fact that the cruising world as a whole is NOTHING like the BVI, where you can find an anchorage, and white sand beach, a beach bar, and a restaurant within 15 minutes of wherever the need for those delightful luxuries arise. The seas are almost never angry, the anchorages never rolly, and the wind a perfect 15-20 for sailing and 5-10 within the protected confines of the hundreds of anchorages available. There's a reason it's the most popular chartering destination in the world. Even the rest of the Caribbean doesn't resemble this. You come to realize that this is a good thing in many ways once you've been in the life a while and you start seeking seclusion more often than a crowd. But still, at first it can feel like a slight letdown. What do you mean there's only one anchorage on this side of the island? And did you say there's no groceries to be found without a taxi ride? And you can only catch a taxi after a 40 minute walk? And why is this sand so rocky? And why am I being blasted with 25 knots of wind for 5 days straight???


And now of course, I'm making it sound like a nightmare that no one in their right mind would put themselves through willingly...just charter a couple weeks a year and be happy with it. But that's just it...if it was easy everyone would do it. And even in this age of internet everywhere, an app for everything, and all our human whims easily satisfied with barely any effort required, many people still realize that doing the "hard" thing rewards you with a sense of accomplishment and pride that can't be recreated in any other way.


Now when we do find that perfect idyllic anchorage, it looks all that more perfect. And when we figure out the tricky system of where on a island to get what and how to do it, we begin to feel just a little bit like locals even though we're in a strange land and everything looks and feels more familiar; more comfortable. And when you find yourself in the right spot at the right time and have the good sense to drop the workload for a few days to hit "5 Bays in 5 Days", you get to relive what inspired this life choice in the first place.


Maybe just like in land life we only live the idyllic version of a cruising life for maybe 2 weeks out of the year (okay, probably 4-5 at least), but we get to do it in the midst of accomplishing things we didn't know we were capable of, and thriving in a situation where we're utterly detached from the grid of society. The sense of self and connection to the world this affords us is irreplaceable, not to mention the lessons we hope it's teaching our son. It's NOT always fun...that's just life in any form. But it IS always an adventure and a learning experience daily. Now the "5 Bays in 5 Days" stretches that so resemble our charter days mean so much more. And a sundowner in the cockpit in ANY port

can still make you feel like you're winning.

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