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.

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.

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.

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.

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