When Does Cruising Really Start?

I’ve learned a lot of lessons from cruising, and some I hope I’ve learned. The importance of being present to what’s happening, even while deep in the midst of prepping to leave, is one I’m still working on.

I was 21 when Jeremy said 4 words that would forever change my life.

He waited until the waiter at the pizza place had left the menus, then leaned in.

“I’ve got something to tell you.”

I stared at my hands. At him. At the menu. It’s likely there were tears in my eyes. Was this the break up talk? At College Inn pizza, on a Friday night, surrounded by strangers? My brain raced with the what ifs. Am I the only one whose brain goes immediately to “what did I do wrong” when someone says those words? It feels like being back in the principals office.

The waiter came back. I’m pretty sure I ordered something – that is, after all, what you do when you’re out for dinner. The waiter went away and my fear rushed back in. My mouth went dry and my hands got clammy.

The words came as if from a far distance. “Let’s buy a boat.”

Jeremy, walking down the Lawn on graduation day.

I can still vividly remember the almost levitating feeling of relief. “Is that all?”

“I want to go cruising.”

He’d been sailing and talking about sailing for as long as I’d known him. We met on the sailing team at the University of Virginia (we sailed on a man-made inland lake about 25 miles away), and he’d been teaching sailing on big boats in the Bahamas and the Eastern Caribbean during spring break and summers since his first year at school.

This wasn’t that big of a surprise. How hard could this cruising thing be, anyway? It’s like a fulltime vacation, right?

So we graduated, landed jobs, and moved to Texas (in 1991, there were not many options for a non-US citizen in a really awful job market) with this goal in our heads. The apartment was chosen because it had the all-important second bedroom – not for guests, or for a kid, but for the wooden dinghy he started building even before we unpacked all the boxes. Evenings were spent eating rice and beans (to save money), poring over cruising guides and boat magazines, endlessly discussing the kind of boat we should buy and where we should go. By the following spring we’d found the boat, the 28’ Bristol Channel Cutter we still own, adopted a beagle, and began the cruising prep in earnest.

It was decided. A 2-year cruise was what we could swing, we thought, based on a pulled-from-thin air budget of $1000 a month. Our destination? The Bahamas and the Eastern Caribbean, though the idea of a Caribbean circumnavigation was entertained more than once. Every instant was spent talking about the boat, working on the boat, or discussing the cruise. Was there anything other than the future?

Cruising prep involves a lot of projects, a lot of lists, and a lot of learning. I remember certain moments about those 3 years, but mostly I remember worrying about what was next. A project was finished (putting the head on the boat, building the galley) and immediately the next one started. Enjoy the process? Who has time to do that, when the TO DO list was longer than I am tall. I think I took maybe 3 pictures the whole time, mostly of the mess or of the dog curled up in some corner.

Questions swirled. Would we be able to get the finished dinghy out of the room it was being built in? How would the dog do on the boat? What would life be like in such a small space? How could I cook aboard? Could I get tired of beaches? What actually do you do on a boat all day?

The next three years flew by in a blur of endless boat work and more endless driving (my commute was 70 miles each way, and we carpooled together to save money), and on September 10, 1994, we slipped under the Kemah bridge and into Galveston Bay with enough gear on board to put us down an extra 2 inches on our lines, towing that dinghy (it came out of the room!) and followed by a few friends on their own boats cheering us on as we headed off for our adventure.

I found one of the log books we kept during that first cruise, a map-decorated hardbound journal. Here are some of the entries.

July. We leave in 2 months to go cruising. It’s starting to be real. We’re prepping now – we’ll really be cruising once we leave the dock.

October 10: One month in. We need to find a place to tuck the boat while we head back to Houston for an appointment. When we get back from that, we’ll really be cruising.

November 25: Thanksgiving tied to the dock at Dotty and Waldy’s, finishing up the dinghy seats. They loaned us a car for easy provisioning. Next stop, the Dry Tortugas. When we get there, we’ll really be cruising.

December 25: What a crappy Christmas. It's dumping rain and howling wind. We're all alone in the anchorage, with canned ham, canned peas, and canned potatoes for Christmas dinner. We leave for the Bahamas tomorrow. I can’t wait to really be cruising.

May 1: We leave for Rum Cay tomorrow, then on to the Turks and Caicos. I think this is where we really start cruising, when we leave the Bahamas. I wonder who we’ll see there.

When I re-read logs from the first year, the “we’ll really be cruising when . . .” line is repeated over and over again. It almost makes me sad to go back and read it. Not for the adventures and mishaps that are chronicled, and not even for the sense of nostalgia as I read the words written by 24 year old me. But the constant looking ahead, FOMO even then. That was a lifetime ago. Have I learned anything since then?

How much cruising, how much life, did I miss wondering when it was going to start?

We are less than 2 years out from our next cruise, this time with a timeline of “as long as it’s fun.” There are lots of projects. Incredible lists that now have titles like “selling the house” and “getting the kids settled in college” and “MUST DO BEFORE WE LEAVE”. The learning feels just as steep, though a few of the worries are just not there any more. There’s no dinghy being built in a spare bedroom, no concerns about “what do you do out there all day?”

I’m trying to be present, to focus on what’s happening now. I know that this part, the prep part, is as valuable and as valid a part of cruising as any of those perfect sunsets or incredible beach walks.

It’s all cruising. No waiting required.