Decision Time

So now we come to the crux move. It’s decision time. And as those of you who know me can attest, I torture myself over personal decisions. I get there, eventually, but it’s never easy. Here’s where I’m at right now:

Further in the boat lift headed back to the water after being treated and released by the boat docs

Further is back in the water after a few days on the hard having the shaft seal and two through-hulls replaced. So I am mobile once again. And the Salty Dawg Rally, for which I am already registered and paid, is scheduled to depart Hampton, Virginia (at the lower end of Chesapeake Bay), tomorrow morning, and there’s no way I can get from Annapolis to Hampton by then (it’s about a 20-hour trip on the boat) and I’d want to spend a day or two in that area resupplying before heading offshore, so that’s out, right?

Well, the weather router who does forecasts for the rally said conditions over the weekend did not bode well for a Saturday departure and instead advocated leaving Monday afternoon. That’s doable for Further and I. And even if it isn’t, we could still head out to sea later in the week or next weekend or even later in the month.

But here’s the thing: I’m nervous. Scared, even. Yeah, I said it. I’m scared.

No, I’m not scared about the boat sinking or dying or hurricanes or anything like that. Further is a sound, ocean-crossing vessel, and the weather can be forecast (to a point, but to a point where severe stuff can be dodged over the course of a weeklong trip).

I’m nervous about all the things that can go wrong that are way less than sinking but still significant. Things that are significant financially, to be blunt.

The canvas dodger, which protects the cabin, is disintegrating after many years in the sun. I haven’t been able to get the rig (the mast and the shrouds that hold it up) checked. The jib has some tears in its edge. The engine runs fine but it’s old. The newly replaced shaft seal still leaks—but it will for a little while until the flange seals with use. And I wonder about just how much it will cost to live down in the Caribbean.

Every single one of those fears has a rational counter. I don’t need a dodger, and I now own a heavy-duty sewing machine so I can patch the holes (once I learn how to use the damned machine). The rig is and has been solid, as far as I can tell. I have some sail tape (and the aforementioned sewing machine) with which I could fix the jib (not that I know how). The engine, as I said, runs fine. The flange on the shaft seal will seal soon. And the guy who redid Further’s electrical system, a local boat-whisperer who knows EVERYTHING about boats and cruising, remarked the other day that living in the islands is, “on the cheap.” Hell, I even have a willing—nay, gung-ho—crew rarin’ to go.

So why the fear? The answer: I don’t know. I’ve always been one to jump at chances. Case in point: I got offered the job in Alaska on a Thursday; I was on the road on Monday and in Anchorage on Wednesday. That’s impetuous. And I didn’t just visit Montana, I moved there.

So again: why the fear? Is it age? Could be. A lot of people ask me how I can afford to do such a trip and the answer is: if I were a typical modern American, I can’t. I’ve spent a significant chunk of my retirement on chasing this boat dream. And I haven’t worked in two-and-a-half years. Having some money coming in rather than just going out would be a really nice change.

To that end, there is one job opportunity here in Annapolis that is intriguing. (The interesting job in D.C. about which I wrote earlier evaporated; my friend and former coworker found what he called “a slam-dunk candidate” who got the gig.) But there is a yacht brokerage agency is looking to pay someone for some office/marketing help—someone to help with their website and social media and such—while also training that person to become a broker. I have no interest in being a used-car salesman, but such a situation might be a way for me to break into the marine industry. This agency believes I might be that person and wants to talk later today, and I am inclined to listen.

Along another line: earlier this week I sent out an invoice for some freelance copywriting I did for another former coworker of mine. That felt good: doing the work and then issuing an invoice. It was just a few hundred dollars but still, it’s a start. Or it could be. Do I stay here in “society” and try to establish a freelance career? If I could get that going, that would be something I could do from anywhere—say, on a boat in the Caribbean. Do I stay in the States (if they still exist after Tuesday’s election) and address the issues/concerns I have about Further while also building up my cruising kitty and establishing an income source for the future, all while living in a place I like and where I have a lot of friends, and then go next year? It’s a compelling argument.

And then there’s this fabulous quote from late actor Sterling Hayden. The guy was a movie star, but before that he grew up in a rough-and-tumble orphan’s existence in Massachusetts and Maine, and he became a Grand Banks fisherman and then a sea captain. As a captain, he even ran guns for what was then the CIA into what was then Yugoslavia during World War II. In short, the guy was a badass. But he has this fabulous quote to which I return again and again:

To be truly challenging, a voyage, like a life, must rest on a firm foundation of financial unrest. Otherwise, you are doomed to a routine traverse, the kind known to yachtsmen who play with their boats at sea…”cruising” it is called. Voyaging belongs to seamen, and to the wanderers of the world who cannot, or will not, fit in. If you are contemplating a voyage and you have the means, abandon the venture until your fortunes change. Only then will you know what the sea is all about.

Granted, that’s easy to say when you’re a movie star and can fly back to Hollywood to make a cool hundred grand in a month (exorbitant wages in those days) whenever you’re broke, but the sentiment remains. (And the continuation of that quote, the first one on this page, is equally brilliant.)

But all the signs I get from the universe tell me to go. I even changed my phone’s lock screen from a photo of the late, great Spoondog to an exhortation that reads, “Life will only change when you become more committed to your dreams than you are to your comfort zone.”

And that’s what it all comes down to: stay in my comfort zone or chase my dream. In years past, I’d have already leapt. And I started my leap with this dream. But for some reason I’ve paused at the end of the diving board. Whether I take the plunge or tiptoe back to the pool deck will be determined in the next few hours. Stay tuned.

Return to Naptown: An Update

Put this guy to work scaring off the 30-plus ducks that were overrunning Stella’s Marina. He did his job well.

Apologies for being radio silent since I brought Further south to Annapolis. Yes, I’ve been busy but I’ve also been lazy, too. And a tad frustrated. Details on all of that follow.

So, the plan was to be here in Annapolis for a couple of weeks, primarily to help a friend with her booth at the U.S. Sailboat Show and also to get some work done on the boat, before wending my way down the Chesapeake to Hampton, Virginia. I would be there for a week or so, linking up with the Salty Dawg Rally and departing offshore for Antigua on 3 November.

Well, the boat show was interesting. I’ve done the show most years since 2011 but this was the first time I actually OWNED a boat. So instead of being a show of daydreams, the sailboat show became a show of “do I really need that?” and “can I actually afford that?” Between that personal shift, and the very real sense that the show was smaller and had less stuff than usual, and this year’s U.S. Sailboat Show was kind of a downer.

Still, I did buy a few things, including some nesting kitchenware that fits in my galley (so I could ship my Calphalon pots back home to Plum Island), some odds and ends, and even a long-desired sewing machine. That’s right: I bought a sewing machine. And I’ve spent time since the show learning how to use it. It’ll be a while before I’m whipping out awesome canvaswork, but it’s a-comin’. You just wait.

Enjoying a glass of wine by the fire at Stella’s Marina

It was around the time of the show that I discovered that Further was in need of some work. The shaft seal—where the propeller shaft passes through the hull of the boat—developed a slow leak. Not enough to sink the boat but enough that I was wary of going offshore without fixing the situation. In looking back over the receipt from when I had the engine checked out last March, I rediscovered this tidbit: “Packing box is out of adjustment range (PSS over compressed). Replace when needed.” So it was really nothing new, it just wasn’t pressing…until now.

Thing is: to replace a shaft seal means pulling the boat out of the water, and boat yards hereabouts are pretty busy this time of year. I found one yard (where my friend, Renee, had a ton of work done on her boat last autumn) able to do the work. I spoke to them early last week, at which time they said they’d get the parts in first and then I’d bring the boat over for them to haul out and do the work—Thursday-Friday of last week, or maybe Monday-Tuesday of this week. I got an email from them last night saying the parts will be in by the end of day THIS Thursday, meaning the work won’t begin until Friday. And it’s a two-day job, minimum, so I’d have to scrounge up a place to stay over the weekend (I can’t live aboard while Further is out of the water). Sigh. I’ll talk to them today about when the work is ACTUALLY going to get done.

As evidenced by the yard, the marine industry here in Annapolis is very much on island time. I’ve written about this before: “No worries, mate” and “Soon come” and “Mañana” are the M.O.’s in Naptown. So my guess is: I’ll take the boat over on Monday, the work will get done Monday through probably Wednesday (because a two-day job will invariably take longer than two days), and then I’ll be back in the water.

But that means I’ll be back in the water too late to join the Salty Dawg Rally. As a result, I’ve been pretty despondent since last night’s email. Hell, I even had one or two quality people lined up to go along as crew for the trek. Really. Again: sigh.

In the mud yet again. Compare how the stern is up out of the water…

No matter. I know I have it good and easy compared to billions. My town didn’t get nuked off the map by a hurricane a couple of weeks ago, I have a roof over my head and food on the table, and despite being stuck in the mud in the marina (as I experienced so much last year), things in Jones Cove are quite enjoyable. Oh, and I’m quite certain I’m going to win that $1.6 billion lottery tonight, too, so there’s that.

…with the waterline in this photo. Further afloat in her slip…what a concept!

And if going south doesn’t happen (although there’s no reason I can’t go on my own, separate from the rally), there’s an open slip at a nearby marina with deeper water AND a couple of job prospects here in the Annapolis/D.C. area, so another winter in Naptown may be in order. And in a worst-case scenario, I could haul Further out of the water, winterize her and go back home until spring.

Autumn twilight over Jones Cove

So there’s a lot on my plate right now. And then there’s the little fact that the Red Sox start the World Series tonight…

The Best Laid Plans

I mentioned at the end of my recap of the sail to Annapolis that I had some pondering to do regarding next steps. That may come as a surprise to those who read my recent post laying out my plans for this fall and winter. Namely: heading to Annapolis, then down the Chesapeake and then, in November, heading offshore with the Salty Dawg Rally to Antigua. “Life is now,” I wrote, and I was emphatic in my declaration(s).

Well, the journey south last week has given me pause, and I am now having some second thoughts about my plan to go offshore. It’s not that I don’t think Further can handle the trip. Quite the contrary: the boat is bomber, made to go offshore fast and in comfort. And it’s not that I don’t think I can handle the trip, though I will say that I have more faith in the boat than I do in myself. But last week’s trips shed some light on certain aspects of both me and Further than have me, well, pondering.

As for Further, again, she’s solid. The hull and rig are made to go, even in the lousy conditions we endured last week. But some of the auxiliary aspects on board the boat are a concern.

For instance: the dodger, the canvas “windshield” that sits at the front of the cockpit keep that area relatively dry is a shambles. That’s not a big deal—Magellan and Capt. Cook circled the globe without a dodger—but not having a dry spot from which to handle the boat is a drag and can be a safety factor when it comes to fatigue over time. I’ve looked into replacing it since last spring but canvas workers both here in Annapolis and back home in Newburyport were too swamped to take on the job and they still are.

And my jib is showing signs of wear and tear. Do I really want to get down to the islands and have my jib explode? That would suck, to put it mildly. Now, I read about sailors down there making do with jury-rigged sails after they lose a mainsail or headsail and can’t afford a replacement, but is that really how I want to tour the Caribbean?

Similarly, after last week’s fun and games, I’m kinda thinking I’d like to have a smaller jib at the bow of my boat. It makes no sense to have a sail, as I do now, that is reefed 90 percent of the time you use it. Better to have a sail sized properly for the prevailing conditions—and be a little under-gunned at times, then to be putting undue stress on your primary driver. But getting a new sail made is not going to happen in the time frame I’m dealing with, never mind the fact that I don’t have the money for a new jib.

There are also a whole host of little items that, taken together, make things a pain in the ass when the going gets tough. I still can’t seal the windows in the cabin top so they leak a bit when taking on heavy water; the hatches on the foredeck also seep a bit; the one fridge is such an energy suck that I wonder if the electrical system could keep up its needs in the hot climate of the Caribbean (another fridge works fine) without having to run the engine (and thus burn diesel which costs money) all the time.

And then there’s the fact that I still only have a year under my belt with Further. What is there on board that is on the verge of giving up the ghost and, since I don’t have a lot of time with her, I won’t know it’s coming until I get out of the country? Maybe I need more time to really know her inside and out?

Again, at her core, Further is a beast. A fast, beautiful beast made to go to sea. But all those side items add up to make me nervous sometimes. Like, say, in the middle of last week’s tumult.

As for me, well, I’ve been offshore. Several times. And I’ve been in some bumpy water and relatively high winds. But I’ve always done so as crew, never as captain. And going offshore as captain is a whole other ballgame, as I learned last week. And what I learned is this: I can’t do it alone. And not just any crew will do. I need people on board I can trust and in whom I have complete confidence. Last week’s crew, Capt. Ed, is one such person. But as last week showed, two is not enough. At least not yet in my captaining experience, anyway. Someday, I hope to be just two on board: me and my significant other. And we’ll know each other—and the boat—so well that we can handle everything thrown our way. But until that time, I need a few experienced and/or game folks along for the ride (three other people would be optimal). And they’re hard to find.

I’m on a couple of crew-finding websites and several people have expressed interest. Some of them are experienced sailors and quite intriguing. But I don’t KNOW them, so I’m wondering about how much confidence and faith I can have in someone I don’t know, especially if we’re five days into a 10-day offshore passage and the weather turns to shit.

And then there’s the ongoing question in my mind, one I’ve raised before: namely, do I want to go on such an adventure alone? Let’s say I find decent crew for the rally south; once I’m there and they all head back to the mainland, I’m on my own. I’m sure I can handle the boat in that situation, but do I want to? As much of a hermit as I can be, that might be biting off more than even I can chew. Wouldn’t it be so much better to have someone along to share the fun? Even if I had several friends come visit over the course of the winter, wouldn’t it be better to have someone equally invested in and excited by such an adventure?

So this is what weighs on my mind in the wake of last week’s trip through the rinse cycle of a washing machine. And it is these things I will ponder in the coming days here in Annapolis.

Fortunately, there are alternatives available to me. Maybe Further and I will motor our way down the Intracoastal Waterway (after the water in the Carolinas clears up in the wake of hurricane Florence) and spend the winter in Florida. The Bahamas are an easy jaunt from there and I’ve long wanted to go back to the Florida Keys, a place I’ve not been to since I was a little kid. And I hear great things about places in between: places like Charleston and Savannah and such. I could spend some time exploring and adventuring in a place where there are resources readily available and not have to venture offshore for a week-plus.

Maybe I’ll stay in Annapolis another winter, only now that I know the area and the scene and the Chesapeake better, I can build more experience all winter long AND use the town’s yachting resources to address those items aboard Further I listed above. And, in fact, I mentioned in a post script in my “Life Is Now” column that there’s a job opportunity that very much intrigues me. Well, it’s in Washington, D.C., and if that should pan out, staying in Annapolis would be a great way to resume my career AND keep building up my boat-management chops AND be in a place that I very much enjoy and where I have friends and a good life. I’ll be exploring that possibility while I’m here; I’d appreciate it if you’d cross your fingers for me on that one.

So, yeah. There is much to ponder. It all seemed so clear a couple of weeks ago, but a tumultuous jaunt across a couple hundred miles of Atlantic Ocean last week jostled that clarity quite a bit. Stay tuned for the next installment…