Best Time To Go Cruising?

When people find out we spent six years commuter cruising the Western Caribbean, inevitably there are comments like:  “we’re going cruising, right after …. “.  There are gazillions of “right afters”, most of them entirely valid.

Crystal clear waters, sugar white sand, living the dream.

Crystal clear waters, sugar white sand, living the dream.

But if you really want to leave the country and “go cruising”, whether it’s for six months at a time like we did or full-time, there will never be the perfect time.  Children, elderly parents, grandkids, finances, needing a bigger boat and overall uncertainty are all high on the list of “reasons” that finish out the “we’re going cruising, right after……”.

Unfortunately there are innumerable “wild cards” out there that often seem determined to thwart even the most determined.    Health issues are the biggest of the wildcards.  It’s a fact, as we age, health issues arise.  And often thwart dreams of all kinds.

No one can tell you what’s right for your cruising dreams.  There are no right and wrong answers.  We’ve met families with small children to octogenarians all happily cruising the Caribbean.   All of them had something in common though.  They all decided what they were willing to give up in exchange for fulfilling their dream.  There is no free lunch.

Staniel Cay Yacht Club Docks.

Staniel Cay Yacht Club Docks.

We miss our granddaughter Gilly’s birthday every year, we missed holidays with family (plan to make up for it with “Christmas in July” — there are other alternatives to get family together and make memories), and many other things that we’d like to be around for, but there’s no way to leave and go cruising without missing out on something.  At least in our experience.  There’s always something … a birthday, holidays, a wedding, a graduation, the list goes on and on.     If we hadn’t agreed that we’d block an entire six months to devote to cruising, we’d never have been able to check that cruising dream off our bucket list.

If you are determined, arrangements for “life” can be made — one “reason” for not going cruising that I particularly hate is “I have to be around to deal with taxes”.   REALLY?  I cannot believe anyone lets taxes prevent them from achieving a dream.  We estimate, prepay our taxes via quarterly estimates and get an extension.  When we return from cruising, all the paperwork is there and we file our taxes.  Learn the rules and don’t let something stupid like “taxes” get in the way.   Medications can be challenging, but there are ways to figure it out if you’re determined enough.

Exploring paradise in our dinghy.

Exploring paradise in our dinghy.

Back to timing:  our logic was that we’d retire early and go commuter cruising six months a year as soon as our youngest son went off to college.  The advantage was that all three kids were happily busy with their own lives and didn’t really have much time to spend with Mom & Dad anyway.  And since we were/are commuter cruisers, we’re at the lake all summer when they feel the urge to go wakeboarding or skiing.  We had no grandkids yet, in fact, none of our kids were even married yet.

Our parents were approaching “older”, but were still living their own lives busy with their own friends.   Since all the family was busy, it seemed like the perfect time to go.  Oh wait, at the time I had my own company and David had his family owned business … after serious deliberations that lasted about a couple of seconds, we decided to sell both businesses to help finance our dreams.  We also sold my house and David’s truck – we didn’t really need two houses and three vehicles.  And we were young and healthy enough that neither of us had to worry about prescription medication refills.

We bought the boat four years before we planned to leave, which wasn’t exactly fiscally the best choice since we all know about B-O-A-T (bring out another thousand).  But it was the right decision for us because it gave us time to get the boat equipped and learn all the systems before leaving the US and becoming dependant on us to diagnose and fix stuff.

Make plans to realize your dream and sail off into the sunset.

Make plans to realize your dream and sail off into the sunset.

So if you have a dream, don’t just dream.  Sit down and talk about what’s right for you and come up with a “plan”.    It can change, but at least it’s a step in the right direction to actually making it happen.    Discuss what important life events you’re willing to “give up” and then make a plan to celebrate them at a different time. Decide how you’re going to finance the dream.   Think through how handling “life” will work — mail, taxes, communications, all the things that are impediments to leaving.

As the TV commercial says:  “your dream is out there, go get it”!   Please leave a comment and share how you made (or will make) your cruising dream come true.  Cheers!  Jan


  1. Great tips and encouragement … especially the timely one about “filing an extension” as a way to deal – or not deal – with the taxman. A growing concern and challenging part is getting on the same page when it comes to facing real and anticipated family “obligations.” I’m not sure how you pulled off 6 years in the Western Caribbean, but am sure you are glad you did?

    • Hi Rich! Our buddy boat friends always said “Life is in the timing” — and the six years we got to spend in the Western Caribbean was between most of the family “obligations” intensified. At that point the kids and the parents were both too busy doing their own thing to have any time to spend with their parents/kids. But I know what you’re saying, we did make some hard choices, such as missing our first granddaughter being born toward the end of our six years. Not sure we’d do that again. But yes, we’re happy we had six years — keep in mind, six months at a time — to spend cruising the Western Caribbean. The “off” six months allowed us to catch up and celebrate holidays – Christmas in July was popular until the family moved all over the country and now it’s harder to get everyone together. Cheers! Jan

  2. John & Jane Timmons says:

    We’re on our way. The house goes on the market in a few months. Lots of sailing and navigation lessons behind us. Searching for the right boat. Thanks for the inspiration.

    John Timmons
    St. Charles, MO (formally of Mattoon)

  3. Thanks for helping me keep the eye on the prize, Jan. We have planned to cruise for years and as you say, “things” just keep getting in the way. We have waited too long, but your writing/insights (even with all your enthusiasm) have made me more sanguine/realistic about life aboard…not so excitingly ambitious to have the “big adventure”. Feels better. Just need a new roof on our land base, then all attention is turned to getting MorningStar ready for the southern trek from Annapolis to Bahamas in the fall.
    Bari Spesard

  4. Keith Davie says:

    I suspect “As soon as we finish re-building the boat” is a valid excuse for putting of leaving, but even that I have to watch! The tendency could be to wait until the boat is “perfect” – which of course it will never be!
    But we’re in process, the refit is underway, and 2017 for launching, 2018 for departure is on the calendar. See you out there!

  5. Robert Snelling says:

    I’m working 4-week rotations offshore; by next fall (2016), I’m challenging myself to have the boat in warm waters and ‘commute’ to work. The return flights between Halifax and Freeport, Bahamas, cost the same as the fuel I was spending monthly commuting to work (when employed in a Monday-Friday job). It’s very feasible as I’m still working full-time. Your blog has been an invaluable motivator and resource. Thank you!!


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