Are you a planner or roll with it cruiser?

Feb 6, 1998
11,722
Canadian Sailcraft 36T Casco Bay, ME
I fully admit that my family and I don't really sail with a plan. By that I mean when we plan to head out sailing all we know is we are going sailing for approx XX days and may perhaps have a general coastal vicinity in mind but no more. Other than that we usually have no clue where we are headed. Apparently many of our friends don't cruise this way, perhaps 2/3 of them, and some can't fathom how we do what we do.

Last Tuesday evening friends wanted to plan vacation in order to meet up with us on our cruise. When they began asking questions like "Where will you guys be on Monday.". My wife would say "No idea, probably somewhere in Penobscot Bay". It went on for about ten minutes when my wife's friend became really outwardly frustrated. "How do you guys go sailing for 12 days and not know where you'll be?". To which my wife replied "How do you know where the wind will be three months out?".. I just laughed....;)

When we left the mooring the other day, a late start of about noon, all we knew was we'd come back Sunday or Monday (still on the boat now so apparently it's Monday). As we left the mooring the wind was good for Harpswell and my wife and I just kind of said "Harpswell Sound?". So there we are a few hours later almost to Small Point which is well beyond Harpswell Sound. The sailing was perfect so we just kept going, it's why we own a sail boat. Here in Maine you motor a lot, so when the wind is ripe we take a big bite....

Nearing Small Point my wife looked at me and said "Sebasco Harbor?". The wind was still good so I just shrugged a "perhaps" sort of look. An hour later, wind still excellent, and we were approaching Seguin Island, well beyond Sebasco, and my wife said "What about Five Islands?". Again I gave her the "perhaps" shrug and we kept on sailing. As evening was approaching we were nearing Damariscove Island. My wife looked at me and said "Damariscove?". This time I grabbed the binocs and counted four masts in a two-boat cove, "Nope, not Damariscove.".

I fell off a bit and we headed up towards Squirrel Island and we wound up in Boothbay. This morning we ran into some friends who were shocked we were there. They planned their trip months ago, reserved a mooring and took two days to get there. When they heard we'd left at noon with no plan to even go to Boothbay they were quite stumped, especially seeing as we had a spot in the inner harbor right next to them...

We love the spontaneous nature of sailing without any hard plan but realize some are really out of sorts without a full blown itinerary...

Are you a planner with a set firm destination, or do you roll with the wind & a whim?
 
Feb 10, 2004
4,184
Hunter 40.5 Warwick, RI
We have a general plan but it gets adjusted as we go along. We generally stick to the plan even if the wind is not the best. If the wind is really unfavorable, we change our plan. We really should be more flexible, but if we have a certain number of days and want to go to a list of spots, then we need to do more motoring.

Hence the sailing criteria:

You can select a destination.
You can define a schedule.
You can sail.

Please pick any two.
 
Sep 15, 2009
6,244
S2 9.2a Fairhope Al
i like what you have written in your post and i like the fact that you do it that way ( it's a good way to ward off disappointment of failed or changed plans )...serendipity ( the devil may care sorta of thing ) is always good ....planning is for practice.....being flexible is the way you have to deal with the wind so why not do voyages that way to ....i don't like dead lines when it comes to leisure time it take the relaxing out of relax time
 
Oct 2, 2008
3,811
Pearson/ 530 Strafford, NH
Maine has so many options that it is easier to alter plans. Further along the coast south our options get fewer. We wait for good weather to do the longer days otherwise our Monday is from October to June. (not so much this year)

All U Get
 
Oct 26, 2008
6,370
Catalina 320 Barnegat, NJ
I like your "plan" ... spontaneous works best for me. But it makes a big difference to have options.
 
Feb 9, 2008
292
Catalina 22 Long Beach Harbor, MS
Good post! That is how i discovered my love for night sailing. Nearing harbor at sunset, wind perfect, keep going! Sometimes the conditions are so right (you, the boat, the wind, the water are as one) you just have to stay in the moment.
 
Feb 6, 1998
11,722
Canadian Sailcraft 36T Casco Bay, ME
I like your "plan" ... spontaneous works best for me. But it makes a big difference to have options.
I do recognize that we are very lucky here in Maine, with literally hundreds and hundreds of options.... My Grandfather used to take my dad and his brother cruising and my grandmother would often stay behind on the "boys trips".. "When will you be back?" she'd ask, and my grandfather would simply say "When we're done.";) They would often be gone for a week or more and would occasionally hit shore and call home..

It's not that we don't ever have a plan but it is much rarer for us to have one than to not have one...
 
Jul 27, 2011
5,144
Bavaria 38E Alamitos Bay
I suppose we can appreciate a slight modification of General Eisenhower's famous quote: "In preparing for battle [= ocean sailing] I have always found that plans are useless, but planning is indispensable."

It's sort of the way I look at it. Yes, we have planning--sometimes rather extensive planning. I wouldn't say that plans are always useless; sometimes, perhaps, if the trip is very long in days, weeks, or in distance. Obviously, if you're outside your "planning" none of the associated plans would work. It's also like the relationship between strategy and tactics. For example, my strategy might be to arrive at destinations in time for a nice afternoon happy hour in the cockpit, securely anchored; so I plan a route compatible with that. Tactics would be how I "execute" that plan, including the option of alternative destinations, even delayed departure, if things go to s..t!:D

Another "strategy" or planning in venues where the wind blows predominantly from the same direction [California coastline] is to make the most up-wind destination(s) early when weather predictions are more certain; return by sailing downwind to home, etc. The actual selection of "stops" awaits the "mood of the day", as in Maine Sail's scenario.
 
Oct 3, 2008
325
Beneteau 393 Chesapeake Bay
It depends. I often sail with a group of friends, each in their own boats, and we meet up somewhere to raft up. So, in that case, some planning is needed. However, if we are out by ourselves or just going for a day sail, then I don't plan much at all and just go where the winds take me.

It's funny though, because many of my boating friends like to plan where we are going days in advance and every once in a while, we all agree in the morning after a raft up to go "wherever" and meet "there". Really gets some of them disturbed.
 
Jul 27, 2011
5,144
Bavaria 38E Alamitos Bay
Last year near this time my group of companion boats were anchored in Pelican Bay in windy conditions [see my avatar of that morning]--the most up-wind destination of those planned. Our route plan was to go to Little Scorpion that day to anchor there for the night but we ended up at Yellowbanks on the south coast of Santa Cruz Island instead. Nobody sweated that; much better protected there!!
 
Oct 4, 2010
7
Pearson 323 Rockland
Weekends are generally unplanned, unless I have made prior arrangements to meet up with friends. My longer cruises are generally part of my Power Squadron cruises, which are planned in April. But even those are "subject to modification" as needed when we set off.

Much is wind and weather dependent, but it's always nice to have a goal. As I moor in Rockland, Maine the "goal" for the week long cruise is generally Downeast, often to Northeast Harbor or Roque Island, with variations. Weekends are easier, as there are many, many quiet anchorages around Vinalhaven or the many islands south of Deer Isle.
 

Robin3

.
Dec 29, 2014
14
beneteau oceanis36cc Daytona Beach
after a lifwtime of cruising different boats different areas;-

weekends, go with the flow

Vacation cruises, we used to have 2-6 weeks, have a provisional pencilled in plan to have some idea of latest date to start the return and make it back work on time and in between when and where to restock food, charge batteries top up water tanks, do the laundry etc. In later years when I ran my own business ( now retired) I could be more flexible and 'work' from the boat

We cruised in Europe where tides (heights and flow rates) and weather were critical decision makers and right place right time had to have some kind of planning. There were times and places when we would plan to wait for the morning seabreeze to build before upping anchor and other times when we would leave at night for a lighter wind or breeze off the land. Tidal gates were places where you had to pass with a fair tide or spend hours motorsailing and still going nowhere fast
 

zeehag

.
Mar 26, 2009
3,198
1976 formosa 41 yankee clipper santa barbara. ca.(not there)
schedules wreck boats.
the more ye plan the harder the gods laugh...
remember my plan to get to caribbean in x number months...rodlmffao----

ROLL WITH IT!!!!!!~~~~~
 
May 23, 2004
3,319
I'm in the market as were . Colonial Beach
I have a general plan but I then alter it a lot. I generally know when I am going out. Once out of the Potomac I then like to see what the wind direction is blowing before I head a direction.

If you plan you will usually end up fighting the wind, motoring all day, or something like that. Heck, the best made plans still have issues!!

Go out, have fun, come back in time, and all is good.
 
Jul 27, 2011
5,144
Bavaria 38E Alamitos Bay
schedules wreck boats.
the more ye plan the harder the gods laugh...
remember my plan to get to caribbean in x number months...rodlmffao----

ROLL WITH IT!!!!!!~~~~~
IMHO, planning and "scheduling" are not exactly the same things; you can have planning w/o "scheduling."
 
Feb 26, 2004
23,131
Catalina 34 224 Maple Bay, BC, Canada
...or do you roll with the wind & a whim?
You mean there is another way?

How could that be?

. I generally know when I am going out.

Go out, have fun, come back in time, and all is good.
As a singlehander, too, I rarely know.

But once I do leave, I remember to bring myself with me and enjoy myself, as long as I write down that's what I should be doing. Oh, and when!!! :eek:
 
Sep 17, 2012
112
Morgan 383 Fairhaven, NY
The Admiral & I do a week or two cruise on Lake Ontario. We leave a float plan at our YC with a "be back by" date. Our actual itinerary is dictated by the weather. We don't transit across the big lake when its angry. NOAA marine weather is frequently inaccurate but they usually get the "big stuff" correct. It takes 8-10 hours to get from the 1000 Islands to NY south shore. The bad news, it can be a long, pukey, rolling day with short frequency 8 footers from the NW. The good news it'd be a beam reach!
 
Sep 16, 2013
38
MacGregor 26S Peoria, IL
Interesting post and I agree with most of these replies. Regarding safety, Zeehag has it right - sticking strictly to a schedule can lead you to make some very bad decisions.

Our recent cruise of the Grand Traverse Bay & Manitou Islands on Lake Michigan is a great example of how we cruise. Working with our friends who were sailing with us, we selected our starting point and made reservations based on launch ramp and trailer storage, central location, etc. From there, we selected ports we wanted to visit and left the details to the day of departure based primarily on weather. In actuality, we did get to visit every port and then some, however, our plans did change daily. That's what works for us!
 
May 4, 2005
4,062
Macgregor 26d Ft Lauderdale, Fl
Maine has so many options that it is easier to alter plans. Further along the coast south our options get fewer. We wait for good weather to do the longer days otherwise our Monday is from October to June. (not so much this year)

All U Get

1+ in SE Fla, you have more limited options. and the wind is typically E-SE.

once in the islands there are many more options.
 
Jan 12, 2011
930
Hunter 410 full time cruiser
For a longer trip like a week I start out with where I wish to go for the first long leg, which depends on where the wind is forecast to blow for the next two days. There once I leave I have a couple of ditch points in case the weather guys lied!

After that my plan mostly is that I have to be back by a certain date and I fill most days till then based the forecast that morning. This sometimes means I head back sooner because it looks questionable to do a couple days later.