The boats at anchor all look so pretty and the thought of living on one seems like a dream come true. But how do you know if it's really for you?

How Do I Know If I’d Like Cruising?

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.

Boat Shows

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.

The boats at anchor all look so pretty and the thought of living on one seems like a dream come true. But how do you know if it's really for you?

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  • Rebecca Guthrie
    Posted at 14 March 2017 Reply

    Good article Carolyn. Always enjoy your blog it has such good advice. Getting ready to make this type of life style change is not something anyone should take lightly, yet for those who choose to do can compare their feelings to a moth being drawn to the light.

  • Beverly Schaefer
    Posted at 14 March 2017 Reply

    The United States Sail & Power Squadrons offer several boating courses. First and foremost is the ABC Safe Boating Course. After that there’s Seamanship, Piloting, Advanced Piloting, Jr. Navigation, Sail, Weather, Cruise Planning, Engine Maintenance and so on, just to name a few. Cost is reasonable. Courses and materials are designed at the National level to ensure consistency. Instructors are all through local Squadrons and are usually very good. I highly recommend these courses.

    • Carolyn Shearlock
      Posted at 14 March 2017 Reply

      Power Squadron courses are an excellent resource, but they tend to be more “skills oriented” and not introductory “see what cruising is about” type of classes. Once you think you’re really interested, they are a wonderful resource!

  • Patricia McLean
    Posted at 15 March 2017 Reply

    Very good article! You are absolutely correct that the only real way to be sure is to actually do it for a while. We did all the shows, took many courses including liveaboard courses, lived on our boat during vacations and weekends. But we discovered that living aboard full time is different. And we also discovered we don’t enjoy it as much as we thought we would. Turns out we are very social and prefer to be near shore with lots of other folks around. And we love the opportunity to get away from the boat for day trips.

    So instead of heading to the Bahamas and further south on our boat, we decided to live on the boat for summers (in Canada) and take a travel trailer south during winters. That compromise lets us enjoy the boat for as much as we really want without it becoming a chore or a bore.

    Everyone has different needs and experiences – Hopefully each family finds their perfect solution!

  • Donna Chiappini
    Posted at 16 March 2017 Reply

    Great advise Carolyn. We started our sailing experience by taking classes in San Diego. Started on 22′ boats and worked our way up to 32′ before we bought our own. As we got to larger sizes we chartered for the weekends and actually stayed on the boats and got used to staying in small quarters. After 4 years we purchased our first boat; a 393 Beneteau. We had chartered the same boat and were already used to it’s size and style. We have since upgraded and learned a lot about what we did and did not want in a boat. Having just chartered in the BVI’s we are happy to go home to our own boat in Southern Cal.

  • Eve
    Posted at 17 March 2017 Reply

    My husband and I are looking forward to cruising when we retire in about 6 years. We love sailing and powerboating and charter every chance we get … but no guaranty we will love living aboard for long periods of time, so we are planning on keeping our house.
    We started out thinking we wanted a sailboat, but now we think we want a powerboat (trawler), to make it easier to do the Great Loop and continue safely aboard once we are too old to be climbing a mast.
    Since we started our boating education in 2011 (after having owned a small powerboat), we took all the ASA sail classes and now working our way through US Sailing’s powerboat courses.
    We are members of a local sailing club in the San Francisco area where we can charter cruising size sailboats or powerboats as often as time and funds allow. We travel for a week-long charter each year on a boat similar to what we think we want to buy someday. So far, we’ve done longer trips on catamarans in the Caribbean and Bahamas, and powerboats in the San Juan Islands.
    We also go to a lot of boat shows to check out used boats and also the new ones that maybe we can afford used in a few years.
    All of this has really helped us to focus in on what we want and do not want in a live-aboard boat. The boating and navigation skills we are learning help us to feel confident that we can safely live aboard someday. Carolyn’s blog is great – a very “real” look at what it’s like to live-aboard and full of valuable tips that make even weekend cruising safer and more enjoyable!

  • Wayne Ezekiel
    Posted at 17 March 2017 Reply

    Wonderful information as always.

  • lori
    Posted at 27 March 2017 Reply

    liked your timely (for me) article. will send more comments later. thanks, Lori

  • Ellen Zimmer
    Posted at 30 March 2017 Reply

    Good article – I also wanted to mention “boatbound” link is

    It is the “airbnb” of boat chartering. You can charter all kinds of boats with either a captain or bareboat. My husband and I did this for 4 days last summer – a 28′ sailboat on the Chesapeake . It was a great test for me as we did not go ashore the entire time – gave me a flavor for what it would be like living on a boat – cooking, washing, showering etc. Living in small quarters. This was much less expensive than some of the other charter companies. But it all depends on the type of boat you charter and the owner’s charges.

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