How To Overcome the Obstacles to Cruising

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Obstacles to Cruising


by Colin Ward


Colleen and I recently spent a weekend with a couple of old sailing buds we had not seen for several years.We were all lake sailors and racers together throughout the eighties and nineties. Our friends have plans to go sailboat cruising when they reach retirement age. Since we have been cruising for about six years ourselves, guess what quickly rose to the top of the pile of subjects to be discussed. After our friends left to return to work, I started thinking about all of the cruiser wannabes out there and the reasons that many of them will never leave the dock.

Before I dive into the topic of cruising obstacles, I should reflect on what is important to our friends versus what is important to us at this point in our cruising lives. About six years ago, we outfitted our boat and made most of the decisions about the boat and cruising equipment we now use to lead a thus far comfortable, successful and safe cruising life. I remember having our own five year plan that ultimately got us on board and underway in 1999. We owned our present cruising boat for two years before we departed on our first lengthy cruise. We devoted lots of time and money during those two years to preparing the boat.Air conditioning was added first so we could stand to do the rest of the projects in the Florida heat. Then came davits, radar, autopilot, wind generator, solar panels, navigation equipment, watermaker, anchors, charts, and so on and so on. Once we left the dock, our attention turned to navigation, destinations, weather, and finally the really fun parts - the sailing, the new friends we met, the islands we visited, the local people, the fishing, the snorkeling, and the activities we got involved in.Fortunately, the equipment and the boat behaved themselves for the most part and the equipment became just the tools of our job of cruising. Presently, we do not spend much time thinking about different boats or newer equipment and I certainly do not relish the thought of any more projects aside from normal maintenance. We rarely read magazine articles about the latest whiz bang technological cruising toys and we seldom listen to Jimmy Buffett because we have our own cruising tales.

Our old sailing friends are on a time line mostly dictated by their corporate retirement program. They plan to begin cruising in seven years. They have purchased a very nice cruising vessel which they will use for weekending on a large lake while they install and improve cruising equipment as their dream approaches reality. While we were together, our sometimes passionate discussions centered around windlasses, batteries, chartplotters, RAM microphones, freezers, storage, dinghies, SSB radios and so on......topics that are critical to them but have been relegated to my back burner. We made our own choices several years ago so I could not offer an opinion on the latest inverter/charger or chartplotter (we primarily use paper charts, although we do have some charts on our computer). It was fun to hear about the choices they are making but I am glad I am not making all those decisions again.

I hope our friends stay on their schedule (or move it up) and get to go cruising on their beautiful boat. Unfortunately, there are a lot of folks with similar dreams who never manage to go. In case you are thinking about cruising yourself, let's take a look at some of the obstacles in the hope that it might help you overcome them.I don't have any statistics to rank the reasons for not making it, but you can guess which ones might be your dreambreaker.




Ignoring those who are very wealthy, there are essentially two ways that cruisers finance their lifestyle. One is to wait until retirement when lump sums, IRAs, and pensions become available, and the other is to save up for a sabbatical from work for a year or two. Some retirees buy their boat with the proceeds from selling their home. They are usually the folks who can afford one of the new extremely expensive cruising vessels that are on the market. Others maintain a home or downsize to a condo and buy a more modest (read “old”) boat. Some rent out their home and cruise on the income. Some return home to work during the off season.We have met younger cruisers on a “sabbatical” aboard anything from an ancient 30 ft Columbia up to a fairly new 44ft Island Packet, but they all regard the boat as a temporary expense to be eliminated when they return to the working world.

What are the pitfalls? Well, needless to say, there are many reasons people do not have as much money as they would like. With respect to going cruising, some of the pitfalls are:


Taking on too much boat  


- either the boat is too expensive to leave any funds for cruising, or the boat is old and worn out and becomes a very large money pit. I recommend going as simple and new as possible. A fixer-upper bought in haste can easily cost years of toil and all the money you have plus more.

Complexity adds tremendously to hassles and costs.We know a couple who purchased a beautiful new and very complicated 45 footer and now sail it back to the dealer's location every summer so he can continue to troubleshoot and repair the systems. Some people not only try to duplicate all the conveniences of a house, but also the local electric company, the water and sewage treatment plant, the cable TV company and the telephone company....all of which are supposed to work in a rolling saltwater environment. Why go cruising if you can't leave Sex in the City and Seinfeld behind?


Underestimating the cost of monthly expenses while out there


I have read books that talk about cruising on $1000 per month. While that much might buy you a few sacks of beans and some fish hooks, it will not go far buying boat insurance and bottom paint, diesel fuel and gasoline, groceries in Caribbean countries, transient slips, flights home, and newfangled gadgets like the telephone. Doubling that number is a more likely minimum.Note that some experts claim that the annual maintenance cost of the boatis 10% of its value.


Wasting too much money on perceived luxuries rather than saving money for cruising. 


In addition to interest on credit card debt, examples of unnecessary expenditures would include $100 restaurant meals, driving (and maintaining) a European luxury car or SUV rather than an economical car or minivan, buying a 4,000 sq ft house for two people, buying snooty designer clothes from the mall rather than no-name clothes from a discount store (all of which were made in the same Chinese factory), getting every family member a cell phone, etc. etc. It is very easy to get sucked in by a barrage of advertising, peer pressure and salesmanship from folks (including marine retailers) who will gladly take your last dollar (and lend you more) if you let them. On the other hand, you don't want to spend 20 years denying yourself all of the pleasures of life while you save for an uncertain future, so you must strike a subtle balance.


When Do You Have Enough? 


Yes, some people do not know when they have enough assets to stop working and start cruising. It's not as difficult to figure out if you have reliable pensions, but what if you just have a nest egg of investments? Check with your financial advisor.....some say you can remove 4% per year for life without depleting your principal - that's $40,000 per year for every million you have invested.

If you wait until the future is 100% certain and the stars are all in alignment, you will never go. When we retired, my employer was obligated to provide low cost medical insurance as part of the deal. But three years into retirement, the news came that “whoops, the company will not be providing insurance any longer”. Of course that was a blow, but we came up with alternatives that allow us to continue cruising. Not every event can be anticipated.


Buying and Selling a Boat for a Sabbatical


The financial exposure for a sabbatical cruiser is the cost of outfitting the boat, the depreciation, plus any taxes and broker fees which cannot be recouped when the boat is sold. Also, you may be paying dockage and loan payments for the time it takes to sell the boat which is usually measured in months if not years.

I do believe that a cruising sabbatical is a life changing experience. Afterwards, the cruiser will likely be looking for work in the great outdoors and will not take Dilberts in cubicles too seriously. They will also remember how happy they were aboard that 1969 Columbia 30 and live less materialistic lives than their peers.




With the exception of the sabbaticallists, most cruising is done by people who have reached an age when health issues raise their ugly heads more frequently. Cruising itself is a pretty healthy lifestyle if you limit your exposure to potluck dinners, but often the damage has already been done. So cruisers have to plan for doctor visits, filling teeth and prescriptions, etc. etc. Needless to say, many health issues are manageable while cruising, but others are simply incompatible with a rolling vessel, with time spent out of the homeland, or with anchoring near a remote island with no possibility of seeking medical help when the weather turns bad. Sometimes it is possible for a spouse or crew to move the boat to the next port where the less healthy cruiser flies in and joins the fun. One of our friends actually crewed on a large motor yacht that was also staffed by a pair of nurses who took care of the elderly owners who would not give up boating and had the funds to insure they could continue.

Medical care outside the US is much better and cheaper than our gummint would have you believe, but for something serious, the US, Canada or Europe are your best bets. In the Caribbean, the French islands would be my first choice.Be prepared to educate your doctor about your lifestyle and your need for several months of prescriptions at one time. Chances are good that the doc, like most other dirt dwellers, knows little about sailing or cruising.

Pleasure is in the Preparation

We have encountered some would-be cruisers who derived great pleasure from designing, building and preparing their ideal cruising boat, but did not enjoy cruising at all and gave it up almost immediately. They were Type A perfectionists who loved the challenge of knowing everything about boats and doing absolutely everything themselves. They could not chill out and go with the flow once they started their voyage. Someone else wound up with a great boat.Know thyself!




Grandchildren have killed cruising plans for more sailors than you might imagine.Having no offspring myself, I can only report my observations, but it seems to be Grandma more often than Grandpa who cannot tear herself away. Older grandchildren can come and visit the boat in an exotic location, but the reality is they would rather be with their friends at the mall.


Aging Parents


As we reach retirement/cruising age, our parents are probably reaching an age when they need a lot of care. Many cruisers recognize their needs early on and manage to arrange for family care or for help through assisted living facilities or nursing homes. It is hard getting a call informing you that one of them has passed away while you were out of touch on the boat. On the other hand, many feel that they cannot spend their own golden years waiting around for an unpredictable event. Parental needs have definitely prevented some from going cruising and have limited the wanderings of others. Fortunately, communications and air travel are pretty good in a lot of the prime cruising grounds.


One Half of a Couple Hates It


Here is another tough one! Chris has dreamt of cruising for decades and is loving every minute now the time has come. Pat, on the other hand, gets seasick, is petrified of lightning, misses workmates and HBO, and thinks Chris is incompetent and is going to get them both killed. There is a slim possibility that Pat may come around or that an arrangement can be made whereby Pat flies in to join the boat when Chris brings it into the next port. More likely however is the ultimatum “choose me or the boat”......and sometimes the boat wins.




Deciding whether or not to obtain a pet and take it cruising is not too difficult. Deciding what to do about 12 year old Fido who is part of the family is another story. Lots of people cruise with cats and dogs. Cats can survive within the confines of a boat with few ill effects if you don't mind dealing with a litter box. Dogs on the other hand like to go ashore, run around and take care of business every few hours. When we were lake sailors, our dog was always with us and we dutifully dinghied her ashore multiple times a day. She was totally house trained and only once had an accident on the boat in sixteen years. Unfortunately, that otherwise desirable trait is unworkable in the cruising environment.Even motoring down the ICW does not offer the opportunity to anchor and take the dog ashore for a bathroom break with that kind of regularity. Some friends made costly nightly stops at marinas along the ICW just to be sure a canine potty break would be available.Another friend has trained his dog to use the deck at will, following which he sloshes buckets of seawater on the excrement. We always wear shoes when we visit his boat.Other cruisers we know are reluctant to go very far on their boat because of the declining health of an older furry family member. You should be aware that the Bahamas requires health certificates and paperwork for pets, while some other countries will not allow shore visits at all without a six-month quarantine (only for the pet!). Some of those regulations are loosely enforced but you never know..........




Seasickness can also prevent folks from going cruising. Seasickness is truly debilitating and miserable. The seasick person may just feel a little queasy or may be completely useless and incapable of functioning at all. Susceptibility to seasickness varies by individual from practically none at all, to throwing up when the boat is still on the trailer. Most people are somewhere in the middle of this continuum. One certainly gains sea legs after being on board for a while - even a rolly anchorage helps. Medications vary from pretty effective to little more than a placebo. The effective ones have side effects. Better find out what you can tolerate before you buy your world cruiser and head across the pond. Chartering for a couple of weeks is a good way to test the waters without committing your life savings.


The Naysayers


If you talk about your cruising plans and dreams to your colleagues and relatives who do not share them, you will run across people who think you are nuts and will try to do the right thing and talk you out of going. Some will offer sound analyses derived from the above list and others will simply warn you about the dragons and sailing off the edge. Most are just jealous couch potatoes. Listen to them politely and then do what you think is right for you.

I am sure there are obstacles to cruising that are not mentioned above, but I have tried to cover the ones that we have seen first hand on more than one occasion. Notice that some of these obstacles will keep you from going cruising at all, while others may only limit your cruising grounds to safer, smoother waters like the ICW. You do not have to be a circumnavigator to be a cruiser. Some people are happy as a clam migrating from New England in the summer to Florida in the winter year after year. Truth be told, circumnavigators are often edgy people who love jumping out of aircraft, cave diving, or covert ops in third world countries - not your typical cruiser.

We are thankful that we were able to start cruising at a relatively young age and we sincerely hope our friends on the seven year timeline can overcome all of the obstacles that will crop up.I also hope that forewarned is forearmed and that this information might help you foresee and overcome any obstacles to your cruising plans. In the USA, the cruising lifestyle is being challenged by real estate developers, by anchoring restrictions, by disappearing boatyards, by a lack of maintenance of channels and markers, and by ever increasing costs. If you want to go cruising, I suggest you do not wait too long.