
Are you just starting to think about cruising on a sailboat or a trawler? Are you wondering what it’s really like and how you go about making it happen?
On one hand, there’s a lot of information out there about cruising on your own boat. On the other hand, it’s like trying to drink from a firehose. Where do you start when you don’t know anything? It’s easy to get lost in the details when you don’t know what the big picture looks like.
So let’s look a bit at the “big picture” of cruising. What is cruising really? Can someone like me actually go cruising?
Let’s start with a video of photos taken in my 11 years of cruising and living aboard a boat. First are some pictures of what the living space looks like on several different boats, then photos from our day-to-day life.
You probably notice that I’ve included both the fun, amazing times that are part of cruising and also the work and tough times. It’s easy just to focus on the good times and ignore the harder times when you’re first considering cruising. Don’t. While parts seem like a vacation, it’s not. It’s a way of life.
The good parts are really, really good. But they don’t come free. There’s a lot of work involved; I think the good times are even sweeter because of what it takes to experience them. I love it, you might also. But it’s not for everyone.
Before you start asking about how to buy a boat, learn to sail and navigate or move aboard, let’s explore a little more of what all is involved.
Cruising in General
There is no single definition of cruising. There’s no one type of cruising boat. That’s the beauty of cruising on your own boat: you can generally pick and choose the parts that you want and you may find that what you want your cruising to be changes over time.
That said, sometimes you can’t have everything you want: for example, it’s hard to cross an ocean and not be willing to repair anything that breaks. One option would be to cruise only near your home port and to employ a mechanic to keep your boat in tip-top shape. Another would be to learn to maintain and repair your boat so that you can go to progressively more remote places or cross oceans.
Most of us have a dream of cruising that includes clear blue water, white sand beaches, and tropical sunshine. But the reality at least part of the time may be lumpy seas, squalls, sunburn, biting insects and frustration getting needed parts. If you want to go cruising, you have to be willing to not just accept those days but smile your way through them.
Want to learn more? Take a look at these articles to dig deeper into whether the reality of cruising appeals to you:
Could I Cruise?
The short answer is that almost anyone can cruise — if you really want to. You can find ways to deal with almost anything that seems like it would be a problem, although the solution may involve changing your plans a bit — but I bet not as much as you think!
Most medical conditions can be accommodated; I’ve met a number of cruising sailors with heart conditions and cancer. I know of two amputees who cruise solo. In Mexico, we met a cruising couple who were both legally blind and another cruising family with two of seven children in wheelchairs. CPAP machines (for sleep apnea) can be run onboard. Lots of people cruise with kids and/or pets. If you want to do it, there are ways to make it happen! Wanting is the key; it’s not always easy, so your desire to make it happen has to be strong.
Read more:
Could I Afford to Cruise?
The other big roadblock to cruising is how to finance it. It’s pretty hard to cruise if you don’t have at least a little saved up, but it’s totally possible to start with just a little in savings and then work as you go. If you fall into this camp, a great book to read is Get Real, Get Gone: How to Become a Modern Sea Gypsy and Sail Away Forever.
Cruisers tend to fall into two camps: those who are working as they cruise, either part-time pretty much all the time or full-time in spurts; and those who saved up and are now taking a sabbatical from work or are retired. And it’s not uncommon for some of those who had saved up for their cruise to end up back in the working group.
More on the costs of cruising and how to do it:
Next Steps
Think cruising is for you? Depending on your background in boating, I’d suggest a basic sailing course, an exploring cruising charter or a captained or bareboat charter for your next vacation. See if you like being on the water as much as you like the pictures of it!
Assuming you do, get out on the water every chance you get. You don’t have to go on boats that you think you might cruise on — any experience is good, even things like canoes, rowboats and pontoons. Crewing in sailboat races is a great way to build skills but be sure to get on with a captain who wants to teach. We did 6 charters, several weekends cruising with friends on their boats and two longer “delivery” trips with friends.
Keep reading. Watch informational YouTube videos. Walk the docks every time you’re near a marina. Talk to the boat owners. Take ASA or Power Squadron courses.
And then one day you’ll start looking at cruising boats for sale on Yachtworld . . .
Flatten the learning curve with practical how-to info that gives you the confidence to step into life aboard.
Start Learning Today

Carolyn Shearlock has lived aboard full-time for 17 years, splitting her time between a Tayana 37 monohull and a Gemini 105 catamaran. She’s cruised over 14,000 miles, from Pacific Mexico and Central America to Florida and the Bahamas, gaining firsthand experience with the joys and challenges of life on the water.
Through The Boat Galley, Carolyn has helped thousands of people explore, prepare for, and enjoy life afloat. She shares her expertise as an instructor at Cruisers University, in leading boating publications, and through her bestselling book, The Boat Galley Cookbook. She is passionate about helping others embark on their liveaboard journey—making life on the water simpler, safer, and more enjoyable.
Leave a Reply