Downsizing to Live on a Boat: Where to Start

When you’re downsizing to live on a boat, the way to start is to begin early, pick something easy and unsentimental, and decide each item’s fate the moment you touch it. That single habit, deciding on the spot instead of building a “deal with it later” pile, is what turns an overwhelming job into a manageable one.

Cruising comes in all forms, from weekends afloat to annual charters to a one or two-year mid-career break, part-year cruising, or going full-time. Almost all of it involves some downsizing, whether you’re moving to a smaller house or apartment to afford the boat, or selling everything for the financial and logistical freedom of living aboard.

But thinking about culling an entire house’s worth of belongings is daunting. Overwhelming. Even paralyzing.

I’ve done it three times now. Once to move from our house into an apartment before a lot of land travel in the late 1990s. Again in 2002 and 2003, when we moved aboard our first cruising boat, Que Tal. And again when we made Barefoot Gal our full-time home in 2015. Somehow, between each of those moves, we’d managed to collect more stuff than I thought possible.

Here’s how to get through it.

Start Downsizing Early

Start early, and start with the things that will go quickly and easily. You want to see fast progress, because progress is what keeps you going.

Don’t begin with something sentimental that’s going to be hard to let go of. Save those for later, after you’ve built some momentum and gotten comfortable with making decisions.

Touch Things Once

When you pick something up, decide right then what’s going to happen to it. Don’t set it aside to figure out later. If you do, you’ll just end up with everything in a “decide later” pile, and you’ll be no further along than when you started.

There’s one fair exception. You may have a few things you want to offer to family or friends first. Set those aside, but ask immediately. Take a picture, text or email it, or call. Then if the answer is no, decide on the spot what you’ll do with it instead.

Scan Your Photos

Scanning photos and scrapbooks is a wonderful way to take your memories with you without giving up any space. It takes time, so it’s a great job to chip away at while you’re doing other things.

It’s also one of the best downsizing moves I made, and there’s a faster way to get through it than scanning one photo at a time. Read my article on speeding up the job with a high-speed photo scanner.

Decide Your Basic Categories

Knowing the possible destinations for each item before you start makes every decision faster. When my brother unexpectedly offered some storage space before we moved aboard Que Tal, it was a wonderful gift, but I had to re-sort the entire “put in storage” pile because I hadn’t planned for it.

So decide your categories up front. Will you have a small storage unit? Leave things with one or more relatives? Hold a garage sale? Sell online? Donate to charity? Give things to family and friends? And there’s always the trash pile.

Once you know where things can go, the harder work is physically sorting, labeling, and staging it all, especially if your boat is hundreds of miles away. I walk through the system that finally worked for us, including a color-coding trick and a downsizing spreadsheet, in Organizing to Move Aboard a Boat.

Learn Where and How to Sell Online

If you haven’t sold online before, spend a little time learning the basics before you list anything. The selling landscape has shifted a lot in recent years, so here’s the honest current picture of where to sell.

• Facebook Marketplace: For most people, this is now the easiest place to sell locally. It’s free, it reaches a huge local audience, and it has largely replaced both Craigslist and the old “virtual garage sale” groups for everyday household goods. You’ll still need to meet buyers and handle payment yourself.
• eBay: Best for items you can ship and for specialty pieces that don’t have a strong local market. You pay a fee, but you simply ship sold items out instead of arranging meetings, and payment is handled through the platform.
• Facebook interest and hobby groups: A great way to sell specialized gear to people who actually want it. Friends report very quick sales when items are priced right. You’ll ship and handle payment, but there are no fees. Check each group’s rules on what and when you’re allowed to post.
• Craigslist: Still around and still free, but it has faded for this kind of selling. Worth a listing for larger local items, though expect less traffic than Marketplace.

You may also belong to groups, such as Scouts, a church, a sailing club, or a book club, where you can list and sell items. Learn their rules and listing procedures first.

Meeting Buyers

The biggest hassle with local selling is meeting people. It takes time, and there will be no-shows. If you live somewhere hard to find, know which map services can actually locate you and which can’t. Better yet, arrange to meet at a nearby business. It saves confusion, and it’s smart if you have any security concern about strangers coming to your home.

Taking Payments

Decide ahead of time which payment methods you’ll accept so you’re not figuring it out with a buyer standing in front of you.

• Cash is simplest for in-person sales.
• Venmo, PayPal, and Zelle work well for in-person sales too, especially for higher-priced items. A buyer can pay from their phone and you’ll see it almost instantly. Set up whichever apps you’ll use before you start selling.
• For shipped items, let the selling platform handle payment. eBay and similar sites process the payment for you, which is safer for both sides than arranging it separately.

A little caution goes a long way. Read up on common online selling scams so you don’t get taken in, especially anything involving overpayment or a request to ship before you’ve actually been paid.

Other Ways to Sell

Online isn’t your only option. A garage sale can move a lot at once, and being able to accept cards or app payments can noticeably increase what you sell. We also put some pieces in consignment shops.

For higher-value specialty items, a dealer who knows that category is often your best bet. When I was clearing out, I sold a few pieces to specialty dealers and learned a humbling lesson in the process: many of the things I’d treasured for years had very little value to anyone else. Knowing that early made the rest of the downsizing a lot easier.

List a Few Things Every Day

Larry Webber, one of our team, had a smart approach when he was downsizing. He listed just a few things for sale every day, so he never had to photograph, show, or ship too many at once, and so there was always steady progress.

“Otherwise,” he said, “it’s easy for a week to pass and you still haven’t gotten rid of anything.”

Pick the best venue for each item and list it there. If it doesn’t sell within a week or so, take the listing down and try it somewhere else. Don’t let things sit and stall your momentum.

Timing Takes Precedence Over Sentiment

Twice, we sold our Y-Flyer one-design racing sailboat. The second time, to move full-time aboard Barefoot Gal, was particularly hard. At Dave’s age, the chances of ever getting another one were slim. Dave had sailed Y-Flyers for 50 years, and I’d sailed them for 25. Our home club’s annual regatta was scheduled just two weeks before we closed the sale of our house, and we would have loved to sail it one last time.

But the reality was that all the out-of-towners coming for the regatta were our best shot at selling the boat. And if they bought it, they’d want to sail it themselves, since they wouldn’t have brought their own boat along. So we listed it before the regatta with a specific pitch: “Come sail the regatta in your new boat.” It sold. It was bittersweet to take the check at the welcome-aboard party, but the timing was right, and that mattered more than holding on for one last sail.

Get Rid of Stuff as You Go

Don’t let the piles, whether for storage, family, donation, or trash, grow too large. Get things out of the house as soon as you can.

Seeing the space open up is what keeps you motivated. A pile that lingers does the opposite. It just reminds you how much is left.

Above All, Just Start

Yes, the whole job looks overwhelming. So don’t think about all of it at once.

Pick one cupboard, one closet, one bookcase, or a single box from the attic, and deal with just that. Then do it again tomorrow. The important thing is to keep moving forward and do something every day. You’ll be amazed at how quickly you start plowing through it.

Make a Plan That Actually Gets You There

Downsizing is just one piece of getting ready to go, and it’s a lot easier when it fits into a bigger plan with a realistic timeline. If you’re trying to figure out everything that has to happen to turn your cruising dream into reality, may I suggest our online course, From Dreamer to Cruiser. We’ll walk you through all of it and help you build a timeline that works specifically for your situation.

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