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…