Sailing Totem: Intentionally Unplanned

The wise cruiser has intentions, rather than plans.

October 28, 2019
Catching the sunset from a paddleboard
Floatdowners replaced sundowners in Baja’s summer heat. Behan Gifford

Every journey to cruising is unique, but common themes abound. Our family shares aspirations similar to many who wish to strike out towards the blue horizon: seeking to change lives overfull with things that are urgent, yet unimportant, for a focus on what really matters. We feel the years flying by and hope to slow down, building memories that let us someday look back to smile on a life well lived instead of one with “…wish we’d…” regrets.

Our intention to take a sabbatical cruise of two to five years is either glorious success or utter failure, considering that we are now in our twelfth year of voyaging. I promise this: the open-ended cruise wasn’t something we expected. And yet most of us set out with a particular set of expectations, only to have them evolve along the way. The wise cruiser has intentions, rather than plans.

Pre-cruising days were a hectic collection of going to and from numerous places: work, school, sports, birthdays, shopping, etc. They started early, ended late, and were largely overfull with being busy in ways we couldn’t recall a week later. Weekends broke up the routine of the week, and vacations livened up a season; often well planned to make the most of them, I can’t tell you how most were spent now.

Fishing in the Sea of Cortez
Hand line fishing in the northern Sea of Cortez. Behan Gifford

This may seem pedantically subtle until foul weather holds you up for a week or two. The autopilot becomes less auto, and more kamikaze like. Replacement parts due in “any time now” don’t care about The Plan. Maybe you meet a terrific group of cruisers and your partner or your kids would rather diverge from The Plan for social fun, but captain curmudgeon starts grumbling about falling behind and needing to meet the relatives flying in for a vacation, just a few weeks and many miles away.

Whether cruising is a sabbatical or lifestyle, planning beyond the cast-off date is tempting but tends to result in a flawed list of unlikely expectations. The relative unknowns of a life traveling on the water don’t match well with the strategies of a successful land dweller, and can lead to a very short term as a cruiser. A plan creates a fixed set of expectations whereas having intentions implies the hope of achieving something, but with flexibility.

One thing you can plan on is these types of scenarios happening. Unfortunately, when, where, and for how long are unknowns. This is when stress and frustration creep aboard. If one reason to go cruising is to get away from stress and schedules, why bring it on yourself?


Crow your plans and those back home may actually hold you to them (that bucket-list mindset, again). It’s exciting to roll out a map marked up with a routes and dates, waxing-on about trade winds and cyclone seasons. A year later when your actual location is not even close to what you said, those at home get worried. The “why” question reemerges; followed by articles on pirates and severe weather patterns.

Checking the rigging
Rig checks in Cabrales Boatyard. Behan Gifford

Heading out with unplanned intentions in no way implies a willy-nilly, careless approach to cruising. In fact, having the flexibility of intentions is thought provoking. Unlike a plan devised on a suburban kitchen table, taking into account real variables that shape the actual time and place is realistic. It also keeps cruising fun and exciting. Our favorite anecdote: when long-time cruisers we’d been hanging out with in Mexico decided to head west with the flotilla of friends heading for the South Pacific instead of following their “plan” to go east for the Mediterranean, because – well, why not extend the good times we’d been having together, for the sake of a plan?

Baja from a drone
The beauty of Baja. Behan Gifford

In our coaching work to mentor hopeful cruisers, about 1/3 specifically state the goal to circumnavigate. Others have ambitions that aren’t calibrated to probable success: routing distance better suited to a car going 60 knots than a boat going 6 knots, not understanding seasonal go / no-go timing, and no offshore experience while talking of crisscrossing oceans like it’s a trip across town. A dose of reality, pledge to remain unscheduled, and openness to flexibility. Most fine happiness in a path they couldn’t imagine.


Living a role of supporting dreams, not squelching them, we gently reset and provide context to the real challenges and typical paths. It’s often better to hold plans close and be selective with details, sharing specifics those who will be champions of the hopeful instead of holding their dreams against them. Be open to the definition of success: the enthusiastic would-be circumnavigator may find happiness without leaving the Caribbean, and that needs to be just as OK as looping the globe.


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