We’ve recently met several people who are in the Keys on vacation (by land) and were wistfully staring out at boats at anchor or 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: how does it work, how do we get mail, where did we go, 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 100% foolproof way to find out if you’ll like living aboard a boat and cruising before you’re out there and doing it. But there are a number of ways to see if the reality is even remotely like your dream.
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 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, but you have to be able to do more of it yourself than on land as you may simply be in a place where there is no one to hire. A bit of mechanical aptitude goes a long way, but even just a willingness to tackle something new is an asset.
If you’ve never been on a cruising-size boat, going to one of the big boat shows can give you a feel for what the living space on a boat is like. You’ll be able to go aboard 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 displayed are actually larger than many people cruise. Going to these shows is simply an easy way to go aboard a whole bunch of boats in a relatively short period of time and see what they’re like. Going to some of introductory seminars will also let you see a bit about the 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, and won’t have what you are hoping 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) as well as PassageMaker Magazine’s TrawlerFests held around the country featuring powerboats. There are many smaller shows also.
Chartering is one of the best ways to get a “best of cruising” experience. A week-long charter with a captain is not cheap, but it’s a great way to experience the life and can save you a considerable sum in the long run if you decide you just 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 the workings of the boat.
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 before we made the decision to buy our own boat. All were wonderful vacations in addition to giving us a glimpse into the lifestyle.
Admittedly, a charter isn’t really like being on your own and 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 give a different glimpse of the life than classes and reading.
There are hundreds (thousands?) of charter companies all over the world, ranging from single boat owner/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 are 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 — and they usually offer discounts if you book then!
Numerous classes exist to give you basic and advanced skills both for sailing and powerboating. Many can be done in a liveaboard environment and range from very casual “try boating” days at a nearby boating club or marina to extremely formal classes with extensive 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 ones generally have good teachers and use proven teaching methods, but some people find them intimidating in how much material is covered 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.
The Bottom Line
You don’t have to have been on a boat before you could walk to be a cruiser. You don’t 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; we know many people who take a one- or two-year sabaticcal cruise or cruise 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 love 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.Some links above (including all Amazon links) are affiliate links, meaning that I earn from qualifying purchases. Learn more.