Should You Sell Your House When You Go Cruising?

Should you sell your house when you go cruising? It depends on five factors: whether you’d want to return to this specific house, what happens to it while you’re gone, whether your mortgage requires you to live there, whether you can afford both the boat and the house, and whether selling the house will affect your ability to get boat insurance. That last one is new in the past ten years and surprises most cruisers.

Somewhere in the “planning to cruise full-time” stage, this question lands in your lap. Sell the house or condo? Keep it? Rent it out? There’s no universal right answer, but there is a set of questions that will get you to your answer, and one of those questions didn’t exist ten years ago.

The Questions I’ve Always Asked

For years, when people asked me whether they should sell, I pointed to the same set of questions. These still matter. Start here:

• Would you want to return to this specific house after cruising? Think about the city, the neighborhood, the size, and whether it still fits the life you’d come back to. A house that was perfect for raising kids may not be what you want in your sixties.
• If you don’t sell it, what happens to it while you’re gone? Leave it vacant, hire house sitters, rent it out? Each option has costs, risks, and someone who needs to manage them. Will it drive you crazy dealing with plumbing calls from an anchorage in the Bahamas?
• Does your mortgage require you to live in the house? Owner-occupied loans often do. Read your documents before you assume you can just leave.
• Can you afford both the boat and the house? Add up the mortgage, property taxes, homeowner’s insurance, HOA, management fees, repairs, and routine maintenance. Then compare that to what rent would realistically bring in, after a property manager’s cut. A lot of people discover the numbers are tighter than they thought. If you’re still working out the boat side of that equation, How Much Does It Cost to Live on a Boat? walks through the real numbers.

These questions haven’t gone away. But there’s now a fifth one that can override everything above.

The New Factor: Boat Insurance

Before you decide what to do about your house, call your insurance agent and ask a specific question: will owning a house or condo affect my ability to get boat insurance?

This isn’t a hypothetical concern. More and more cruisers are discovering that having a land residence, and actually spending time there, makes it easier to get boat insurance. Some of the biggest carriers (State Farm and Progressive among them) will not write boat policies at all if the boat is your only home.

I’ll be honest: the logic doesn’t make sense to me. A full-time liveaboard is on the boat, noticing leaks, watching the weather, dealing with problems the moment they happen. That sounds like a better risk to me than a boat sitting empty while the owner is at their land house. But underwriters see it differently, and their view is the one that matters when you’re trying to buy a policy.

Underwriting rules change constantly, and I’m not an insurance broker. I can’t tell you what any specific company will do. But I can tell you this: this question needs to be on your list before you sell anything. If you love the idea of selling the house, starting fresh with just the boat, and simplifying your life, and then you discover six months later that no carrier will insure a liveaboard without a land address, you have a real problem.

For the broader picture on how boat insurance works for liveaboards, including what’s changed in recent years, start with Insurance If You Live On A Boat: Where To Start.

A related piece of advice while we’re on the subject of insurance: investigate it before you make an offer on a boat. Every year, underwriting gets stricter. Every year, more people are surprised at how hard insurance has become to obtain. Do not assume you’ll qualify, even with years of experience on similar boats in similar waters.

One More Piece of Advice: Don’t Sell Everything on Day One

If you do decide to sell, and you can possibly afford it, wait.

Not forever. But don’t sell the house, or everything in it, until you’ve been cruising for at least six months. A year is even better.

The first year of cruising is a steep learning curve. Some people love every minute. Others discover, honestly, that the reality doesn’t match the dream. Knowing that you haven’t made an irreversible decision, that there’s a house to go back to if you need it, makes the hard days of that first year a lot less stressful. It takes the pressure off.

If the numbers don’t allow you to keep the house for six months, consider keeping just the contents in a storage unit while you rent out the house. That gives you a softer off-ramp than selling everything at once. Getting Ready to Start Cruising and Feeling Overwhelmed? has more on giving yourself an out during the transition — worth reading if you’re in the middle of making these decisions.

The Bottom Line

Should you sell your house when you go cruising? It depends on:

• Whether you’d want to come back to this specific house
• What happens to it if you keep it, and whether that arrangement is workable
• What your mortgage requires
• Whether you can carry both
• Whether selling the house will cost you access to boat insurance

Buying a boat and getting it insured has gotten more complex in the past ten years. I don’t say any of this to discourage you. Far from it. I say it because I want you to be ready for the reality, to have thought through every factor carefully, and to arrive at a decision you can live with for a long time.

Figuring Out Your Cruising Plan

If you’re in the middle of sorting out housing, finances, timing, and what order to do everything in, may I suggest From Dreamer to Cruiser? It’s our step-by-step planning course for people making exactly these decisions: defining what you want from cruising, understanding the real costs, building skills in the right order, and creating a realistic timeline so the pieces actually fit together.

Some links in this article (including all Amazon links) are affiliate links, meaning that we earn from qualifying purchases.