My friend Behan, on Sailing Totem, has this saying that she invokes frequently. “Misery is Optional.” This is a great reminder that we can choose our circumstances (or at least our attitudes); when we’re talking about weather and passages, it’s the circumstance angle I want to focus on.

We’ve been excited for this season for a while. Major boat projects will be done, we’ll be in warmer waters enjoying snorkeling and hiking. No more seeing our breath all the time! We’ve done the ICW route a couple of times to get to the Bahamas, and one we’d-prefer-to-forget series of hops to go east from the Bahamas. And while we love the Bahamas, it has been close to 30 years since we’ve explored the Caribbean (other than the Dominican Republic.) We’ve also never been to Bermuda. Perfect, we thought. We’ll go to the Caribbean via Bermuda.

One big reason we’re not opting for the Bahamas this time around is the sheer challenge of getting east from there. The journey from the Bahamas to the Eastern Caribbean is sometimes called the “Thorny Path” - the prevailing winds are easterly, meaning you’re trying to go in the very same direction the wind is blowing from. While it’s possible to do it in hops from island to island, those hops are frequently difficult and any progress hard fought. If you’re not comfortable with multi-day ocean passages, the idea of most nights being safely anchored somewhere can be very reassuring. Because to go direct to the Caribbean from the US East coast is a 1300 mile trip, give or take a hundred miles or so. On Calypso, we’re expecting it to be between 10 and 16 days, maybe longer.

Bermuda would split the trip up. About 600 miles for that first leg, and another 800 for the second. A little longer overall, but shorter duration passages. Hypothetically, you ride the back of a cold front to Bermuda, taking advantage of a shift in wind direction. By the time you get to Bermuda, you’ve done most of your easting, meaning you can do a direct shot to the islands with that standard easterly wind on your beam. Sounds idyllic.

Not so fast. Like, big picture not so fast. Because you need to thread the needle between any tropical systems (hurricane season runs officially through the end of November) and winter gales; the further north you are, the more frequent those gales tend to be. Finding the right weather window just got a bit more tricky.

This time of year is an itchy one for boats wanting to move. A lot of insurance companies have hard and fast rules about timing and geography (stay north of Cape Hatteras until November 1 is common), and rallies have sprung up to offer a “sail in company” community to take advantage of that timing. One of the largest on the US East coast is the Salty Dawg Sailing Association’s “Caribbean Rally”. Boats leave from either Hampton (Virginia) or Newport (Rhode Island) to head to the eastern Caribbean (or the Bahamas); the official start date is November 1.

I think the Salty Dawg is an awesome organization. I especially like the emphasis on making your own decisions as regards to weather; unlike most other rallies I’m familiar with, this one does not have a “start date” that’s akin to a race start. It’s more the gates are open for travel, with weather guidance provided starting even a few days before that. So the “start date” is really a suggestion.

And it is, of course, weather dependent. This year? Chris Parker, the former cruiser/long established weather forecaster who advises the Salty Dawg fleet, had some bad news. A frontal trough in the Eastern Caribbean was stubbornly sticking around and would move west, making eastward travel extremely challenging. Inadvisably challenging. After the third person queried him directly about leaving anyway, he finally said it bluntly. “Don’t go.” He continued to point out that very strong easterlies (and accompanying large seas) made it very likely that if you were headed to Antigua, you’d be lucky to make it as far east as Puerto Rico - and a diversion to the Bahamas was not remotely impossible. Ooof.

(This is second hand information as we are not part of the rally; we’ve got friends who are and they shared some of this. We also can see the boats in the rally from the website and see the questions they are asking during Chris Parker’s regular webcasts. As we too are watching for a good window from the same general location, we’re keenly interested when Chris answers!)

This is a fleet of 120 boats, a large portion of whom have finagled time off work, rounded up crew, bought plane tickets home from Antigua. They’ve stocked the boat with provisions, gotten themselves psyched up to be away from land for 10 days or so. This rude awakening to the realities of life afloat (where the weather rules all) wasn’t something everyone could handle.

Some stayed put. Some went back to home ports. Some changed plans and headed to the Bahamas, or down the coast to Florida, instead of Antigua. Some decided to hell with it and took off anyway.

We’ve been watching this tracker, seeing boats leave after hearing Chris tell them in essence “Be into Bermuda by Thursday night or else be prepared to get pounded”. 2 of the 3 boats that left Newport for Bermuda turned back after 2 days. One boat left Hampton for Bermuda on Sunday; on Wednesday, they turned around. I have to imagine the conditions were just terrible and forecast to deteriorate.

I’ll stress that every boat is different. Every crew is different. Every decision is unique. Weather forecasts are, at best, a best estimate of what’s to come; sometimes the weather is better than the forecast would have you think. Sometimes it’s worse. It’s a little like having a camera with five or 6 different filters you can layer on to see the image you want to create. We make decisions through different filters - and sometimes the deadline filter, or the dream filter, or the “I’ve raced in weather like that and did just fine” filter is in finer focus than other ones.

Behan’s mantra, “Misery is optional”, seems like a hell of a good filter to view things through. Sure, the weather might be better than forecast. But would I WANT to be out there in that?

It’s not that we’re quite ready to go. There are fastener holes on the deck to fill. One last anchor-related piece to craft. We need to button Mischief up properly, and make sure we’ve got all the gear we need aboard Calypso. Still we’re itchy. It’s getting colder and the islands are calling.

But reminding ourselves that “Misery is optional” is a way to calm the itch a bit.