Sail Away, Sail Away, Sail Away: Retiring on your boat

Planning to spend your retirement years aboard a boat and navigating the world seems like a great idea – and it can be one, with proper planning and considerations.

LONG BEACH—Have Boat – Will Travel. No, you’re not looking to navigate the high seas like the gunslinger Paladin, who traveled to Old West looking for work. Instead the open water is where you see yourself retiring. Calling it a career, buying a boat and sailing off into the sunset until Kingdom Come is quite the romantic idea – and something totally possible, if you’re committed to making it happen.

The Log’s Parimal M. Rohit and Kevin Davis have yet another Nautical Banter exchange, this time chatting about the nuances of retiring aboard a boat. Davis and his wife both live on a boat and are planning to retire soon, so he shared his perspectives of what sailing off into the sunset looks like – sure, it’s a lot of work, but you can do it with the right amount of planning and patience.

Parimal M. Rohit: There are so many romanticisms and expectations of buying a boat, retiring from one’s career, and sailing around the world. Obviously, there’s so much more to this than just hopping on a boat and sailing into the sunset. What are some of the realities here that people should know about? 

Kevin Davis: There are so many things to consider before setting off, too much to list. However here a few things to consider: the type of sailboat you’re looking for or can afford; what you need to do to get your boat into shape as well as yourself to set sail safely; where do you want to go; what’s your exit plan; what’s your timeline; what’s your budget (have you put enough away); and, so much more. Before all that, however, you need to build your sailing confidence. Learn everything you can about sailing/your boat, take sailing lessons, learn how to navigate, maneuver your boat under power (get your boat in and out of the docks without damaging your boat and anyone else’s boat), learn as much as you can about sailing techniques, learn the language of sailing (a line is a line, not a rope), read everything you can get your hands on, and watch lots of YouTube videos about sailing. Honestly ask yourself: do I really want to live on a boat/can I live on a boat? Learn how to keep yourself and your crew safe all times. Learn how to anticipate, all the time.

PMR: Following up, what are some considerations anyone should factor in before taking the leap and retiring on a boat (and, possibly, exploring the world)?  

KD: Wherever you decide to set sail, find out as much about the area, the country, it’s language, and its people. Know what documents you’ll need to pass through customs. How will you communicate with your connections back home? What do you do with your mail? How do you access funds? Again, so many things to consider.

PMR: You and your wife are actively planning to retire aboard the IndySent Lady. What was it about the retired-on-your-boat lifestyle that most attracted you? Just the same, what’s your biggest worry? 

KD: It’s a long story about a quick decision. Yes, wine was involved. We’ve always had a gypsy heart. Setting sail just seems natural. Don’t get me wrong, it’s not easy. We don’t anticipate it to be easy. However, part of the sailing life that we enjoy is learning how to adapt and overcome. Our biggest worry is our greatest anticipation – what lies ahead. We’ve not lived or even written that chapter. To borrow a quote from “The Shawshank Redemption,” “I find I’m so excited that I can barely sit still or hold a thought in my head. I think it’s the excitement only a free man can feel. A free man at a start of a long journey whose conclusion is uncertain.”

PMR: Is there anything you think you’d miss once you’ve retired and sailed away? Would you miss this thing so much that you’d reconsider your retirement? 

KD: I’m sure we will miss the niceties and conveniences that we have now. However, moss does not grow on rolling stone. ANCHORS UP!

PMR: When will retirement aboard your boat start feeling real for you (assuming it already hasn’t set in)? 

KD: That’s a hard question to answer. I really don’t know. I guess when we don’t feel Monday is the start of a new school/work week. I believe you trade one thing for another. However, we’re ready to take on the other.

PMR: Tying this discussion to the pandemic, has Covid-19 forced you to reconsider any of your plans? How could a pandemic derail or enhance anyone’s retirement plans (assuming, of course, good health)? 

Right now, NO (fingers crossed). We are keeping our eye on the situation. We are hopeful that by year’s end/early next year things will be back to some normal. Yes, the pandemic has and can derail plans. Fortunately for us it hasn’t much of an effect. No one could have anticipated what 2020 held. However, we have adapted and overcome.


Share This:


Your email address will not be published. Required fields are marked *