“You can’t have a schedule.”
“Schedules will get you into trouble.”
“Always allow plenty of extra time to get somewhere.”
“The weather will dictate your travel.”
“Don’t waste a good day.”
“Don’t waste sunshine.”
Before we start cruising, we hear these words of wisdom from experienced cruisers and think we understand the meaning. But we don’t. Not really.
We’re used to traveling by car, by plane, even by bus, train or metro. We decide when we need to be somewhere, figure out how long the trip is likely to take, give ourselves a little extra and off we go. Maybe rain or snow will slow us down a bit, but land travel is remarkably predictable.
Travel by boat just isn’t. Weather and nature play a far bigger role. Wind. Waves. Swell from a system over a thousand miles away. Current opposing wind. Needing to time a cut with the tide. Where there’s an anchorage. Fog. Lack of wind. Restrictions on entering an area, or exiting.
And, I hate to say it, but there seem to be more mechanical problems with boats than cars. I remember when I was a kid, the family car would periodically break down on a trip. But that’s pretty rare now. We’re not used to delays of that sort — or that we might have to fix it ourselves.
To me, both from our own experience and talking to others, the unpredictability of travel time is one of the biggest lessons of first-year cruising.
Coming from land-based travel, it seems totally reasonable to say something like, “I can easily make 40 miles a day. And where I want to go is 400 miles away. So that’s 10 days. I’ll give myself two weeks since everyone says to allow extra time.”
It might work; more often you might either find yourself making alternate arrangements to get there (such as putting the boat in a marina and taking a bus) or traveling in marginal — or worse — conditions.
The past few weeks I’ve had notes from a couple of readers and seen a whole lot of Facebook posts of people not getting where they wanted by a specified date. One, Larry Webber, gave me permission to share his story to show how the delays just happen. He bought Catriona, a 31′ Pacific Seacraft Mariah in July in Rockland, Maine. The original plan was to start heading south in mid-August.
- Waiting for dock space to install a windvane pushed him back about two weeks from his original “six weeks to make 600 miles” plan to get to Annapolis for the sailboat show.
- A dropped part in murky water caused a 3-day delay in the installation until the third diver called in found it.
- Squally, windy weather delayed departure another 2 days. Needing high tide to leave the dock meant leaving late morning.
- Another day of bad weather along the Maine coast kept him at anchor one day.
- A day and a half of pea soup fog made travel impossible.

- Gooseneck on boom broke, causing him to pull into an anchorage early one day to attempt a repair. It didn’t hold, which caused another short day the next day to stop in Salem, Massachusetts to get supplies for a better fix.

- Holed up in Salem for another day to let the remains of Hurricane Florence pass overhead.

- North winds against large swell from the south kicked up by Florence made for nasty 5 to 8-foot square waves in Massachusetts Bay. Took five days to make 50 miles. Extra miles added to find protected anchorages.
- The Cape Cod Canal has to be timed with the tide and current, and also has to have favorable winds for exiting.
Larry thought that four weeks was plenty of time to go 600 miles from Rockland, Maine to Annapolis for the boat show. The family he’d bought the boat from did the reverse trip with their new boat in two weeks. A singlehander, and new to cruising, Larry admits that he’s still getting into the rhythm of being on the move. And learning to equate weather forecasts with he actually sees on the water. Each decision, taken in isolation, is simple. The cumulative effect of all the individual decisions gets complex.
This past week, he had to make a choice: forget about the boat show (no), sail Catriona to Newport, RI where there is a military marina where he could leave her while going to the boat show by land, or leave Catriona where she was in Scituate, MA and travel by land from there.
At first, he said, “it looked like there’d be a great 4 or 5-day window to get down to Newport, maybe even New London. Then it was a 3-4 day window. Then a half day in the middle of that which was really adverse.” There were also budgetary concerns: leaving her in Scituate would be considerably cheaper than Newport or New London, even with the below-market-rates of the military marinas.
As the weather forecast for getting to Newport looked increasingly iffy, he went with the safe option of leaving her in Scituate. At the same time, he’s questioning not just this decision, but all of them. Deciding to stay in Rockland to install gear. Not pushing harder on good days. Not pushing harder in marginal conditions. Not trying to make Newport.
Larry’s note to me said that the transition to boat travel has been more trying than he expected. “So many parts, all constantly moving!”
From the others who have written me with similar tales, it’s not a matter of being unprepared. Of not knowing how to sail or plan a passage. It’s just that learning to do it day in, day out — figuring tides, winds, timing cuts, figuring stops and backups — is hard. Made even harder by the fact that for however many years we’ve been traveling on land, things usually went pretty much according to plan.
Cruisers joke about plans being written in Jell-O on a hot day, or in the sand at low tide. We say we understand that when we start cruising, but all it takes is our first trip to grasp that we really didn’t. We all start out making plans and having schedules because that’s what we’ve done all our lives. And we soon learn that Mother Nature may have different plans. And hers win.
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Carolyn Shearlock has lived aboard full-time for 17 years, splitting her time between a Tayana 37 monohull and a Gemini 105 catamaran. She’s cruised over 14,000 miles, from Pacific Mexico and Central America to Florida and the Bahamas, gaining firsthand experience with the joys and challenges of life on the water.
Through The Boat Galley, Carolyn has helped thousands of people explore, prepare for, and enjoy life afloat. She shares her expertise as an instructor at Cruisers University, in leading boating publications, and through her bestselling book, The Boat Galley Cookbook. She is passionate about helping others embark on their liveaboard journey—making life on the water simpler, safer, and more enjoyable.
Kimberly says
As brand new cruisers (almost one month now!) who have been trying to go south from New England for the first time, this post really rang true for me. Thanks for showing me that we aren’t the only ones whose plans are continually getting thrown out the window. I’m finally starting to realize that “plans” are truly written in sand when cruising!
Pamela Webster says
And the biggest challenge is not learning the skill set for planning (weather, tides, repairs, etc.) It’s the emotional management.
Anyone can eventually learn to plan boat travel. But only the cruisers who can manage their own expectations and emotions during the process will be successful and content.
Great post!
LeAnn Thurman says
As first-time cruisers, we thought we could make it from St.Petetsburg FL to New Bern NC, making a pit-stop at Marsh harbour Bahamas in 4 weeks. Well, never made it to Marsh Harbour and made it to New Bern NC in 7 weeks. Lessons learned.
Sheila says
We left Toronto August 2nd, 2016, expecting to be in the Bahamas for Christmas that year. Arrived Bahamas January 2018. Family challenges at home, hurricanes, repowering, weather, weather, weather, repairs, repairs, repairs. Want to make God laugh? Make boating plans :-). But along the way, staying in different places for much longer than we expected, we met so many lovely people – both sailors and land lubbers. For that, we are grateful.
Athena Carmichael says
Really the biggest challenge is not learning the skill set for planning. thanks
Jeff Forman says
There’s an old Yiddish saying that I think applies to these dilemmas and to sailing in general…”Man plans, and God laughs”
Fair winds and following seas.