Wondering if you’d like cruising on your own boat?
While living aboard Barefoot Gal in the Keys, we regularly met people on vacation (by land), wistfully staring out at boats at anchor, on a mooring ball, or even at docks.
When they learned that we lived on our boat full-time and cruised, the questions came quickly. They asked how it works. How do we get mail? Where did we travel? What do we do about hurricanes? Do you have to be rich… and then the biggie:
How did you know you’d like it?
There is no foolproof way to discover if you’ll like living aboard a boat and cruising before doing it. But there are several ways to see if the reality is even remotely like your dream.
What trips most people up isn’t whether they like the idea of cruising. It’s not understanding what day-to-day life aboard actually involves.
Just the fact that you’re eyeing the boats means that there is a certain attraction. Before buying a boat, though, take a little time to learn more. You’re likely to save a lot in the long run as you learn what suits you best… or that the whole concept really isn’t a good fit.
What Do You Enjoy?
Living on a boat means spending more time outdoors. The indoor living space is small, but it brings you right into the great outdoors. If you like outdoor activities — camping, canoeing, hiking, swimming, and so on — you’re more likely to enjoy cruising. Are you just drawn to the water? Do you like doing things that are just a little different?
I don’t know that boats really take more maintenance and repair than a house. However, you do have to be able to do more of it yourself than on land. After all, you may find yourself in places where there is no one to hire. A bit of mechanical aptitude goes a long way, but even the willingness to tackle something new is an asset.
Boat Shows
If you’ve never been on a cruising-size boat, attending a big boat show can give you a feel for a boat’s living space. You’ll be able to board many different boats in a range of sizes and from different manufacturers.
Don’t flip when you see the prices of boats and equipment at the shows. Used boats are available in almost every price range. And many of the boats on display are actually larger than those that many people cruise aboard. Attending some of the introductory seminars will also let you see a bit about the cruising life.
There are literally hundreds of boat and outdoor shows across the country. Look for ones that emphasize cruising boats (sail or power) and that have seminars on cruising, not just fishing. For the US, most of these will be on the East, West, Gulf, or Great Lakes coasts. As a general rule, shows that are “RV and Boat” shows tend toward fishing boats and pontoons, not cruising boats. They won’t have what potential cruisers hope to look at.
Major US boat shows are held every year in Newport (RI), Annapolis (MD), Fort Lauderdale (FL), Miami (FL), San Francisco (CA), and Chicago (IL). PassageMaker Magazine’s TrawlerFests held around the country feature powerboats. There are many smaller shows also.
Chartering
Chartering is one of the best ways to get a “best of cruising” experience. There are two styles of chartering to consider.
Crewed Charters
A week-long charter with a captain is not cheap, but it’s a great way to experience the life. It can save you a considerable sum in the long run if you decide you don’t like the lifestyle. And if you do like it, you’ll have a much better grasp of what you do and don’t like!
With a crewed charter, you don’t need to know anything about boating. There will be a captain and cook who take care of all the logistics. Usually, they are very willing to explain how the boat’s systems work.
Bareboat Charters
If you have some boating experience, you can also do what’s called a bareboat charter with no captain. Different companies require different skill levels, with some simply requiring you to fill out a form with your background and others requiring certifications. With many, you can also hire a captain for the first day or two, then go it alone if the captain feels that you have the skills to do so safely.
Dave and I did two crewed charters and three bareboat charters before we decided to buy our own boat. All were wonderful vacations, which also gave us a glimpse into the lifestyle.
Admittedly, a charter isn’t really like cruising on your own. I don’t want to mislead anyone. Planning your own route, watching the weather, buying provisions, and handling any problems that arise all add to the complexity. But a charter or two gives a different glimpse of the cruising life than you’d get from classes and reading.
There are hundreds (thousands?) of charter companies the world over, ranging from small boat owners or operators to large corporations with many locations. Some only charter a whole boat, while others charter by the cabin. While I can’t quite go so far as to say there’s a charter for every budget, there is a wide range of prices.
Large sail and power boat charter companies include:
Boat shows are also a good place to connect with charter companies. They usually offer discounts if you book then!
Classes
Chartering can help you decide whether cruising appeals to you—but they don’t fully show what everyday life aboard looks like. Things like managing water and power, handling trash and laundry, sleeping well, fitting into marina and anchorage life, and dealing with small problems before they become big ones are what determine whether living on a boat actually works for you long term. That’s where education can help.
Numerous classes exist to give you basic and advanced skills, both for sailing and powerboating. Many can be done in a liveaboard environment. They range from very casual “try boating” days at a nearby boating club or marina to formal classes offering certifications. They can also vary widely in cost, depending on the certifications and what is included.
The more casual ones are great for seeing if you like a particular type of boating, but instructors vary greatly in their expertise and ability to teach. More formal courses generally have good teachers and use proven teaching methods, but some people find them intimidating because of how much material is covered and how quickly. Different schools do things on different timetables, so if you are concerned about this, look for slower-paced programs. Look for instructors who are patient and give plenty of hands-on time to each student (small class size is a real plus).
If you are brand new to boating, an introductory class for either sailboats or trawlers is another way to see what it’s like before going further. The two most well-known schools in the US are (both offer programs in the Caribbean islands, too):
I do not know of a comparable school network for powerboat and trawler skills, although there are many local classes offered by licensed captains. Additionally, quite a few ASA schools also offer power classes.
Read Blogs and Watch Videos
No two people’s cruising experiences are going to be the same, but reading blogs by others who are out there can give you a better feel for the day-to-day life of a cruiser. Do the great days and fun destinations inspire you? Or do the bad days and repairs tell you to run for the hills? Do you say, “I could do that!”
You’ll also find some vlogs out there — basically video blogs. The Distant Shores TV show (now available on DVD) is also a good visual glimpse into the cruising life, both the wonders and the maintenance.
Regardless of your age, budget, number of people (from just yourself to a spouse and several kids or even groups of friends), part of the world, and type of boat, thinking of working as you’re cruising or not, you’re likely to find several that sound like what you’re thinking of.
Regardless of your age, budget, number of people (from just yourself to a spouse and several kids or even groups of friends), part of the world and type of boat, thinking of working as you’re cruising or not, you’re likely to find several that sound like what you’re thinking of.
The Next Step
If you’re moving from “this sounds interesting” to seriously considering life aboard, learning how the day-to-day logistics work is the most important next step.
Our online course, The Basics of Living on a Boat, covers the everyday routines, systems, and realities of living aboard—so you can make informed decisions and avoid costly surprises later.
The Bottom Line
You don’t have to have been on a boat before to be a cruiser. Nor do you have to be a multi-millionaire. You don’t even have to do it full-time. We know people who are part-timers or weekenders. You certainly don’t have to do it forever. Many people take a one- or two-year sabbatical cruise or voyage for a while and then move on to other things.
Like most things in life, you can cruise in your own style. Dave and I loved living aboard and cruising; we really missed it when we sold our first boat and moved ashore. After seven years, we bought another boat and started up again. At the same time, I also realize that it’s not the life for everyone. The resources here will help you figure out if it’s for you.
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