The Next Trip of a Lifetime - Sailing Our Boat to the Caribbean

Last weekend we had an amazing day on our sailboat with our friends Dave and Kira. We snacked and drank, swam in the surprisingly warm September waters of Lake Ontario, had a glorious daytime fire on the beach, did some campfire surfing, ripped around in the dinghy, and talked and talked and talked. We were so busy talking and having fun that we abandoned our original plan to drive into Hamilton for a big arts and music festival.

At one point we were sitting around fire discussing our upcoming trip and Kira said, "You know, you guys told us about this trip shortly after we met. You said that as soon as your kids were out of high school and on their own you'd be sailing away."

"Really?" I said as I munched on a handful of delicious Snyders Hot Buffalo Wing pretzel pieces. "I don't remember that."

"Well," said Ana, easing back in her fireside chair. "That would have been about fifteen years ago, memories fade. But I'm not surprised."

"You guys have been planning this trip for a long time," Dave said as he tossed another pile of brush on the fire.

They were right. We have been planning this trip for a long time. In just over a week we will be taking leave from our jobs and embarking on a nearly five thousand mile round trip to the Bahamas aboard our sailboat SeaLight. 

Why now? Three reasons.

First, our parents are mostly healthy. Or better stated, our parents aren't likely to be getting more healthy in the future.

Second, our kids are mostly self sufficient. Sure, they can't cook much, they don't know how to fix a toilet, and they think vehicles are somehow self-gassing. But they are willing and able to figure out these things and whatever else comes their way. The only only real obstacle that has prevented them from learning more life lessons up until this point is us, their parents.

Third, this is the right time for an adventure. Our life of work, eat, sleep, work, eat, sleep, work, eat, sleep, work, eat, sleep, work, eat, sleep, WEEKEND, work, eat, sleep...has become less inspiring of late and we need a break. A real break. Not just a frantic week or two off for summer vacation or a quick winter getaway, but some serious time to reset and refocus. The privilege of waking up each morning not knowing where the day will lead, what incredible experiences we'll have, what disasters may befall us, what characters we will meet, where we will travel to, what we'll find. The excitement of daily surprises. The luxury of an unset schedule.

For us, this trip is an early withdrawal on retirement. It's a learning sabbatical. It's a pre-emptive strike on cancer and whatever other god-awful afflictions may be awaiting us in the future. We're not waiting until we're in the grips of a disease before we start wearing the "Fuck Cancer" t-shirt. Fuck Cancer right now.

The trip will take us from Lake Ontario through the Erie Canal which terminates near Albany, New York, and from there we sail down the Hudson River into New York City. From here, we take an ocean passage down the east coast, past Atlantic City, then up into Delaware Bay and south through the massive Chesapeake Bay, passing by Baltimore and Annapolis with likely day trips to Washington, DC. We will reach Norfolk, Virginia which is the start of the Intracoastal Waterway (shortened to ICW), and this will lead us through a series of rivers, inlets, bays, and man-made canals, all protected from the ravages of the ocean. We will travel through North Carolina, South Carolina, Georgia, and Florida, hopefully reaching Fort Lauderdale or Miami by Christmas, then making the jump eastward across the Gulf Stream to the Bahamas where we'll have two to three months of leisurely cruising through the hundreds of islands and thousands of beaches. Sometime in March, we'll turn around and head back home, returning to Lake Ontario by the start of June. The entire trip will take us eight months.

It's a huge trip, much further than we've ever taken a sailboat. Are we scared? Anxious? A bit. But we've spent the summer toiling on an endless series of boat improvement projects, so SeaLight is as ready as she can be. We've been getting down to the nitty-gritty the last few weekends - selecting the right forks, knives, and spoons for the trip, and in the right quantities. Inventorying every single piece of kit on the boat and removing anything that is not required to free up space for things we do need. Waterproofing the canvas. Loading jars of instant coffee and cans of food into containers in the bilge. We even made a SeaLight Visitor Guide for the folks that decide to join us for segments of the trip.

This is the boating trip of a lifetime and will be a good test as to whether we enjoy the cruising lifestyle. We know it's not going to be easy - navigating complex tides and currents will be tricky and new to us, spending endless days motoring down waterways will get monotonous, the boat is sure to break (likely several times), we will get on each other's nerves, we will get lost and stuck and confused . But hopefully the great days will outnumber the bad ones, and we'll handle the problems we encounter with determination and fortitude. And if it all goes to hell in a handbasket? Well, we'll figure it out. But I think we'll do just fine and have an incredible adventure - one that ushers us into this next phase of our lives.

We're ready.