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Sailing vs. Sailing

Last week I went sailing with my friend Charles.

We cruised out of the marina at Matheson Hammock on Sunday morning and headed south through the Florida Keys. After mooring for the evening in Blackwater Sound, we pulled up to Shell Key on Monday evening. It took us two full days to travel about 75 miles.

Now I've driven through the Keys hundreds of times before – without the undue traffic of an accident on US1, it usually takes about an hour and a half or so.

I've also come down by powerboat, and that took roughly five hours. I bicycled down with my daughter once and getting that far also took about two days. And one time my friend Richard Kane, the founder and CEO of VeriJet, flew me down in his brand-new Cirrus jet. That trip lasted all of 15 minutes, even though we started in Opa-Locka (about 25 miles north of Matheson Hammock) and landed in Marathon (another 25 miles south of Shell Key).

Of course, there are lots of practical reasons why our sail took so much longer; we were at the mercy of the wind, we had to steer slowly through narrow parts of the Intracoastal Waterway, and the obvious point that Charles' 41-foot catamaran is a lot bigger and heavier than my bike, my car, my powerboat, and Richard's jet all put together.

But there's another reason that has nothing to do with the functional aspects of traveling down to the Keys – not the speed of the craft, not the method of propulsion, not the size, not the weight.

Our sail to Shell Key was all about the journey, not the destination. With no particular place to be and no particular time to get there, we removed the constraints and pressures of most travel.

When I'm flying to a speaking engagement, I have to be at the soundcheck, the CEO dinner, and on stage for the keynote at a certain time. I'm usually wondering when the plane will land or when the car service will show up because I have somewhere to be.

It's much the same when I'm traveling for a consulting assignment. My agenda is planned, my objectives are set, and my deliverables are deliverable. I need to be there at a very certain time.

Even leisure vacation travel, which by definition is supposed to be relaxing, is ruled by the clock, what with hotel reservations, theater tickets, museum entry times, and restaurant seating, to name just a few.

But here, our plan was different:

1. Leave Sunday morning.
2. Sail southwest through the Florida Keys.
3. Turn around Wednesday morning.
4. Get back to port before dark on Thursday.

Sure, there were some things we wanted to do:

1. Grab a fish sandwich at Gilbert's in Key Largo. (We didn't, although we did sail past.)
2. Kayak into Lake Surprise. (We did – surprise!!)
3. Kayak around Shell Key. (We did – and saw three pairs of nesting Ospreys!!)
4. Tour Lignumvitae Key (We went on Tuesday, but they're only open on weekends.)
5. Tour Indian Key. (We did – it was the Key's county seat in 1836 and it's still fascinating nearly 200 years later).

But other than those few things, the only thing on our to-do list was to sail.

The word “sailing” is interesting because while the noun has a clear definition of the skill required to operate a vessel, the sport of operating or riding in a sailboat, or a departure time, it also paints imagery of tropical breeze, picturesque skies, and clear, blue-green water.

And while sailing most certainly used to be a means of transportation ruled by time and tide, my experiences last week suggested otherwise. For us, sailing was a journey rather than a destination, a state of mind more than a way of getting anywhere specific.

What I discovered was that sailing, whether actual or metaphorical, is something we should all do more often.