5 Important Considerations Before Retiring on a Sailboat

Retiring on a sailboat is an amazing not to be missed experience!  Toes buried in the sand, snorkeling in the world’s largest and clearest underwater aquariums, immersion in different cultures, watching as the dolphins pirouette off the stern as you sip coffee in the early morning, I could go on and on.  It has definitely enhanced our lives!  But there are a few things that you should consider before you sell everything and sail off into the sunset.

1.   Before you sell everything, stop and think.  Will you want to come back and visit?  What alternatives do you have?  If you want to cruise full time to start, how about renting your house while you’ll be gone.  Admittedly, there are drawbacks and I’ve known cruisers dealing with renter issues but you still have the “homestead” and if you change your minds, there’s a place to fall back on.

Cruising the 10,000 Islands last winter.

Cruising the 10,000 Islands last winter.

2.  Do it sooner rather than later.  David and I were lucky, we sailed off into the sunset for the first time as retirees when I was 49 and David was 57.  Sailing and cruising takes a bit of physical coordination and exertion.  As we age, I’m convinced we get more conservative and less daring … maybe that’s not your experience, but it’s definitely ours.  Even if you take a sabbatical and just sail off for six months and then return to your careers, do it sooner!

The emergency room at San Andres, Colombia ... we waited outside the solid metal doors until they cracked just enough to call us inside ... I was happy to receive good medical care.

The emergency room at San Andres, Colombia … we waited outside the solid metal doors until they cracked just enough to call us inside … I was happy to receive good medical care.

3.  One of the top subjects whenever cruising comes up is medical care … both insurance and actual care.   Insurance is a complex issue and not the topic of this post.  Suffice it to say, spend some time, research the options and make the decision that’s best for you.  Don’t assume that insurance is a deal (cruise) killer, because it’s not.  You just have to manage it — hopefully with the new health care policies, it’ll become easier and more affordable, but who knows.

Because we weren’t traveling outside the US for more than six months at a time, we simply kept our Blue Cross Blue Shield regular health insurance policies until David went on Medicare, then I got my own BCBS policy and we got him a BCBS supplemental policy.  We also added DAN medical evacuation insurance.

Medical care outside the US can be very very good – often with US trained doctors and well equipped facilities at a fraction of the cost.  I had to go to the emergency room in San Andres, Colombia, I had an English speaking doctor (even though I was able to communicate rudimentarily in Spanish), had tests run, we waited for the results for about an hour, then the doctor came back with my diagnosis — a freaky fungal infection, the prescriptions, one of which she just gave me and apologized for the bill being so high and that I’d have to pay it on the spot.  It was $22 US total.  Other friends had major surgery in Guatemala City (removing 12″ of a blocked colon) and paid out of pocket less than their deductible would have been in the US.  It’s a personal decision and the options are too extensive to get into here, but it’s a major consideration.  And if, we needed medical evacuation, DAN’s travel insurance is very inexpensive and works.

David relaxes at the lake cottage with granddaughter Gilly and grandson Dane

David relaxes at the lake cottage with granddaughter Gilly and grandson Dane

4.  Grandkids … even if you decide to sail off into the sunset full-time, you don’t have to give up close relationships with grandkids.  Cruisers skype with their families regularly, providing an outlet where the grandkids can actually see you and you can see them.  Of course, when some cruising friends returned to visit in their daughter’s house, the three year old kept running to the TV — he couldn’t figure out why grandma and grandpa weren’t in that box!   🙂

10 month old Chase pushes 3 year old Rowan in his quest to learn to walk

10 month old Chase pushes 3 year old Rowan in his quest to learn to walk

Another option for older grandkids is to have them aboard.  We have friends that had their 9 year old plus grandson visit them every summer for a month aboard.  He got to experience cruising and when he went back to school in the fall and the teacher asked them to write about what they did this summer, this kid probably always had the most interesting summer…. collecting jellyfish in a bucket, snorkeling, swimming, sailing the boat, exploring exotic locales and playing with other kids from a different culture.  Grandkids can greatly enrich the cruising experience – we can’t wait until ours are old enough to spend some time aboard.

My Dad at 92 and me, nice to have the boat closer to where he lives

My Dad at 92 and me, nice to have the boat closer to where he lives

5.  Elderly parents… they took care of us, now it’s our turn?  We were lucky.  My Mom was fiercely independent and even though she had Parkinson’s Disease early, she managed her own health care.   Her favorite saying was “if I’m going to have to go to a nursing home someday, I’ll pick the very best and pick it MYSELF, thank you”.   And she did.  She chose a lifecare facility which means that they had their own apartment with other seniors making for great social life.  Then when they need more care, my Mom could move to the assisted living or nursing home arms and my Dad could stay in his own apartment.  My Mom passed away years ago, but my Dad is still living in that apartment and loving life at 92.  But he is getting older, so we’re staying closer to the US for now.  Every cruiser makes individual decisions for care of elderly parents.  But it’s definitely a complex issue.

For many, cruising full-time is an enriching experience and they wouldn’t trade it for anything.  For the rest of us, cruising for six months a year, leaving the boat wherever we happened to be and flying back to spend time with family, friends and now grandkids, makes it even better.

Anchored in paradise ... a dream come true that we just keep on enjoying, even if it's different these days...

Anchored in paradise … a dream come true that we just keep on enjoying, even if it’s temporarily modified these days…

A couple more options …  1.  we’ve known cruisers that sell the homestead and buy an RV so they can be mobile.  This would actually work for us since our kids and grandkids are scattered over three states and, of course, none are geographically close together.     2.  we’ve also known cruisers that sell the homestead, but opt to buy a condo in a resort area – something like a snow ski resort – and the entire family congregates there once a year for a month.   They’re full-time cruisers, but take a month break to spend with family.

Downsize, do whatever you need to do, but seriously consider not getting rid of a “home base” until you’ve been cruising for a bit to see if you prefer full-time cruising or you’d be happier as commuter cruisers, like us.

Happy cruising!  Any other important considerations that I’ve missed?  Please leave a comment and share!  Cheers!  Jan


  1. Thank you for that advise … all of it is very good. We are Canadian and will be looking for medical insurance for the States and Bahamas, for 2014. Do you have any information on that ????

  2. The reality side. Go to the Middle East you are safer renting a house in a war zone.

    Maritime Lawyer here: First a boat is a the worst waste of money other than lottery tickets and you have to pay into the Abyssal Plain – it never stops. Items are rare and expansive –the fewer made, the price goes up. Secondly, you are at the mercy of all of mankind’s worst actors even when you are young and on your vessel, be it sail or power. At retirement age you are surely not at your military recruitment best. Coast Guard is to protect the U.S. Coast, not these phony pictures of “paridise”. Also only U.S. flag 1330s are C.G. responsibility. These unfortunates are either being paid or are just a total fraud. Medical Care? Think about it, what doctor is going to do cancer surgery off a boat yard? Death or illness of your family is more likely as you get old. Your kids don’t worship you as you think. Old people are not part of society really. And nobbody is going to buy your condo vacation property when real estate falls – that’s the second worst purchase. Nobody wants you around or your boat with all it’s problems. Retirement is hard enough in place even in well settled cities. Finally some minor points: death of someone, storms, insurance, thieves love marinas. Murder is easy – no body. Just chop and go. Stay home or bareboat charter for a week at the spot you think you are going to live. I have no reason to make this up – who is selling to who? Me or them? Think about it.

    • Wow — I don’t know you, but with that attitude, I REALLY REALLY feel bad for you. No one’s selling to anyone, just making options available. Enjoy your retirement, however you choose to spend it. Yikes. Cheers anyway – Jan

    • Augusto Ferreira says:

      Maritime Layer, I agree that a vessel is a black hole sucking money, specially those parked at Marinas across the country. Now if live in one crossing the oceans at least you are using it and you are fulfilling a dream. If someone has the means and the dream to Sail around the globe why not? Who are you to judge? It takes guts, and good planing. As you mentioned “Old people are not part of society really”, so which one is better , to be forgotten rotting in a condo in Florida or chase you last dream while in this planet. I rather die chasing my dreams.

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