It is a common life theme. The kids are grown, parents no longer require care, and the house is too big and full of a lifetime of stuff. And we wind down our careers or retire.

It is time to make plans for a life change.

I bet this resonates with a lot of people, especially those who live where cold winter weather no longer appeals. Whatever path a couple chooses, it is surprisingly unique to each couple yet about as universal as it gets. At some point the light goes on.

“Why don’t we buy a boat to live on and go somewhere warm for the winter months.” Sound familiar? Find the right place to liveaboard full time for three or more months. It may take a year or two to pull this together, but it is a fun journey filled with anticipation and opportunity.

The Plan has two agendas. First, being settled in one place for the winter is a fine way to spread out, furniture and flowers no longer stored for long days under way. Travel is done, and now it is time to get one of the family cars down to wherever the boat is, likely a liveaboard marina with reasonable monthly rates for slip, electric, and other services.

(Seen below: Stock Island Marina Village allows living aboard your boat in the majestic Florida Keys.)

living on a yacht in florida keys 

The second agenda for The Plan is that living in one place for several months allows each person to decide if this zip code is possibly a place they might like to live permanently when it is time to settle down in the golden years.

The Plan has worked for dozens and dozens of people I know, using their trawler or motoryacht to live comfortably while scouting out a different destination each winter. And somewhere during those years, decisions are made.

The checklist goes like this. Find potential winter havens through the Internet, social media, friends with winter residences, and other resources. The place does not have to be a tropical paradise, just warm enough to enjoy outdoor living. This is not the same concept as finding a fun place to spend the winter and return year after year. For as long as I remember a group of trawler people reconnect with each other every winter in the Florida Keys. It is their ritual. That is fine but not what we are talking about here.

Another important item on the checklist is to find a place where there are things to do, not just hang around the boat and enjoy evening sundowners with others in the marina. This is an important distinction from cruising. You are not on vacation but experiencing living full time in a new place. There must be museums, beaches, shops, restaurants, classes, golf courses, walking and bike trails, whatever fulfills personal interests besides doing boat projects in the marina. For East Coast boat people, this might be Charleston, or Stuart, or Hilton Head. Or Jacksonville, Ft. Myers, or Savannah.

If you live in the Pacific Northwest, one of the best places to retire is in the San Juan Islands. Winters are mild and the summers are to die for. Cruise the area and in time you will find your own sweet spot.

(Seen below: Cruising the San Juan Islands is one of the most visually rewarding boating destinations in the world.)

cruising the san juan islands on a yacht

One way some couples search out possible winter destinations is to take an exploratory road trip. They visit chambers of commerce, visitor’s centers, take tours, and talk with marina managers, other boaters, even yacht brokers. A week or more on the road may be just the trick to scout out several potential places to consider.

The Plan may also include buying a more appropriate boat if the one they own isn’t fit for the mission. A summer cruiser may be fine for that two-week vacation, but not well suited for three months or more. It will be your home, after all, not a camping experience.

While this kind of cruising is quite different from traditional trawler cruising, moving from one paradise spot to another, it can be every bit as satisfying. Shopping for the right boat is exciting. And hopefully The Plan results in an answer to that universal question everyone asks at some point: “Where do you want to live?” These days the answer does not always center around grandchildren, who may be scattered around the country.

In the past couple of years, I have seen many people from my yacht club in Annapolis make such changes, although only a few were consciously working The Plan. The others just decided to run their trawler down the ICW in the fall to escape the cold, and slow down once they reach warmer weather. At some point in their travels, they simply fall in love with a place or are attracted by their friends in Annapolis who are already down there, essentially bringing the community south. Community is important.

For many, the wintering experience eventually leads to the purchase of a townhouse or condo, setting the stage for a long-term winter home base.

The big boat, no longer serving as a winter residence, is eventually replaced by something more suited to the kind of cruising they do in the summer. Just yesterday I spoke with a woman who told me she and her husband traveled down to Florida for several years on their roomy 45-foot trawler, and they became enchanted with the Stuart area. She said there are now about 50 yacht club families who own or rent condos for the winter in nearby Jupiter. So, they bought a condo last winter in Jupiter and replaced their big boat with a Downeast-style Legacy 32 for cruising the Chesapeake Bay during the season. They are thrilled at how it worked out.

(Seen below: Legacy Yachts offers traditional downeast-style cruising in a comfortable and manageable size.)

legacy yachts downeast

If you are at a certain age, chances are you have been thinking of The Plan as it relates to your situation. I have lived in Annapolis on and off for decades, yet I think the time is coming for me to develop one. If you love cruising, you embrace change. And, of course, life is at its best when that change is made by you, not for you.

A mindful approach to where you end up may be the sweetest place of all to be.