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| Our third boat, Ohana, a 28-foot Pearson, sailing in the Gulf of Mexico. |
People often ask us: "I think I’d like to go cruising aboard my own boat but I’ve never owned a boat before and I don’t know how to sail. How do I get into sailing?"
First, we’d like to welcome you. Cruising is great fun. And you will meet some of the most fascinating, incredible people in the cruising community. But for a newcomer, figuring out how to get into cruising can be daunting. There are lots of different pathways to take. There is no single, proper way; everyone is different. But here are our suggestions for how to get into cruising, without risking your financial or physical wellbeing.
Take Some Classes and Get Some Certifications
The American Sailing Association and U.S. Sailing offer a ton of courses for beginners and experienced sailors. These courses are recognized by charter and insurance companies, making it possible to charter boats for sailing vacations in exotic places and, more importantly, to insure a boat that you may buy in the future. When you buy a boat, your insurance company will most likely require you to submit a “sailing resume” detailing your boating experience. If you have never owned a boat before and haven’t obtained basic certifications from ASA or US Sailing, they will probably require you to obtain a certain level of certification from one of these organizations (probably the introductory sailing and keelboat sailing courses). So you might as well do it at the beginning of your learning so that you get the most out of it, rather than waiting until you already own a boat.
Get Out on OPBs (Other Peoples’ Boats)
The courses above are great for understanding the theory behind sailing and for introducing you to some of the skills needed to be a cruising sailor. But you really need more than just a brief introduction to these topics. You need experience, in a variety of settings. So you should sail on as many different kinds of boats, in as many different situations as possible: sailing dinghies, small racing boats, offshore racers, daysailers, coastal cruisers, and bluewater cruisers. You should even spend time on cruising catamarans and powerboats, if you can. You’ll learn new things on each boat. The best way to learn about the art and science of trimming sails and how to make a sailboat go fast is on a racing boat, preferably a small one. Racing also gives you experience maneuvering in close quarters while under sail. But many of the skills needed for cruising go way beyond sailing. Anchoring (arguably the most important skill), engine maintenance, troubleshooting electrical problems, and handling an outboard-powered dinghy are all essential skills, which you will only get on a cruising boat.
So how do you get out on these OPBs?
Go to local yacht clubs, community sailing centers, and marinas. Introduce yourself to the members and staff. If the club has a racing committee, find out who its members are. Let all these people know you are interested in getting out on the water for racing and casual sailing. These clubs usually have social media discussion groups where you can post a message inquiring about potential opportunities. Some even have actual bulletin boards in their lobbies where you can leave a written message.
Contact local race organizers. Tell them that you are interested in volunteering for their organization and in getting out on a racing boat. Regattas and racing organizations often have online crew matching forums.
Use a crew matching service. Racers, delivery skippers, and single-handed cruisers are often looking for crew. (Delivery skippers are professional captains who move yachts from place to place for the yacht’s owners. A delivery can be a few miles or it can be halfway around the globe.) These skippers will sometimes post opportunities for temporary crew on crew-matching sites. Some web sites also allow potential crew to post their profile information and availability so that the captains can search for appropriate candidates. The amount of experience required varies from none to very extensive, depending on the type of boat. Here are some crew matching web sites:
Points East Magazine’s Crew Match (New England Region)
Whenever you interact with any of these people, let them know you are willing to help with maintenance projects in exchange for getting out on the water (learning how to maintain a boat is all part of the process of becoming a cruising sailor). Always make yourself as useful to the boat owners as possible and they'll gladly take you out. Pro tip: bring food or beverage to share. That sort of bribery goes a long way.
In the racing world, you'll likely start out as "rail meat", AKA human ballast. But your role should evolve as you gain experience. If a boat is campaigning in a race series, the skipper and crew may be more willing to take you under their wings if they know you are going to be available for several races. If you can’t secure a space on a racing boat for a particular regatta, volunteer to work on the committee boat or with the shoreside race organization team. You’ll get to learn by watching the races and you’ll meet some of the key people who can help you find a boat to sail on in the future.
One word of caution: before sailing on other peoples' boats, do a little background research to make sure the boat and the skipper are up to the task. It's not such a big deal if you're just sailing in a dinghy on a protected bay, but it's hugely important if you're making a long-distance, offshore passage. Even if that skipper is a professional, talk to other people who have sailed with that person and find out about the condition of the boat and its safety equipment. Take control of your own safety by bringing your own inflatable life vest. If you are going offshore, you may also want to bring tethers, harness (if your life vest doesn’t have an integrated harness), and maybe one or two electronic safety devices such as a handheld GPS, handheld VHF radio, personal EPIRB/personal locator beacon, or satellite communicator. Regardless of whether the skipper has filed a float plan or has a contact person on shore who is designated to be responsible for calling search & rescue authorities in the event that your boat doesn't return when it is supposed to, you should have your own float plan and your own shore-based contact person.
Here's where you can get some example float plans:
BOAT US-Why you should use a float plan (and float plan form)
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| When we lived in Florida, we'd race on Sunday afternoons with the Motley Cruisers on Sarasota Bay. These were cruising boats of all sizes and types that raced in a handicapped pursuit format (all the boats start at different times, according to their time handicaps). They were fun, low-key races and we made it a point to welcome newcomers. |
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| For these Motley races, we'd often swap boats. Sometimes the couples would split up: ladies on one boat, guys on another. Here, Janet was celebrating with her crewmates after a successful day of racing against the guys. Everyone learns new things when they sail on different boats with different people. At the Sarasota Sailing Squadron, in Sarasota, FL. |
Join A Club
If your local yacht club or sailing club is helpful for making contacts, consider joining. You can also join national and international organizations such as American Sailing Association, US Sailing, Seven Seas Cruising Association, Cruising Club of America, or Boat Owners’ Association of the US (BOAT US). These organizations provide many benefits, including giving you access to training resources, introducing you to sailing mentors, and discounts on gear.
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| The Oxford Yacht Club, after the Annapolis to Oxford Race. On Chesapeake Bay, in Oxford, MD. |
Don’t Buy a New Boat!
When you first start thinking about buying a boat, don’t contact a yacht broker. At least not yet. Start out by just looking at a lot of boats. Go to marinas, walk around the docks and look closely at the boats. Do the same thing at boatyards. You can learn more about a boat by looking at its bottom than at its topsides. See what designs speak to you. Who knows, it might be a power boat. (And that's ok.) Figure out the purposes that the designers had in mind when they created that boat. What particular uses would that boat be good for? Is it primarily an offshore racer, shallow water coastal cruiser, bullet-proof bluewater cruiser, floating hotel, dock queen, etc.? Spend time learning about specific boats, boat designers, and boat builders by browsing www.sailboatdata.com. Join the owners’ groups for various types of boats on FaceBook. Ask boat owners what they like and dislike about their boats? Boat owners love nothing more than to talk about their boats. Read reviews of boats published in sailing magazines. Dive down the ultimate rabbit hole of boat porn: www.yachtworld.com. When you have returned to your senses, check out www.sailingtexas.com and www.sailboatlistings.com.
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| A boatyard is like a holy cathedral. In St. Mary's, GA. |
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| You can tell a lot about a boat just by looking at its keel. At Solomons Island, MD. |
Dive Into Boat Ownership: Start Small
After you have acquired some experience and feel it’s time to own a boat of your own, start small. Obviously, the long-term cost of boat ownership increases with the size of the boat. And this cost of ownership increases exponentially with the length of the boat. Costs skyrocket even more when you go from a monohull sailboat to a catamaran.
A lot of new boat owners become overwhelmed by the complexity of their boats. The larger and newer the boat is, the more complex its systems will be. This complexity means that these systems will need more maintenance, and this maintenance will require more advanced technical skills. High complexity also means a high chance of breakdowns and high costs. You will make mistakes with your boat, especially when you are new to boat ownership. These mistakes will likely include some missteps in navigation, maneuvering, and in maintenance. You may overlook some maintenance needs or you may perform some of your maintenance chores improperly. All of these mistakes can result in costly repairs. It is far better to make these early mistakes with a relatively small, inexpensive boat, than with a large, expensive one.
Perhaps the most important reason for starting small is that you will spend more time sailing a small boat than you will a large one. Larger boats require a lot more maintenance. Time spent on maintenance cuts into the time available for actually sailing your boat. And because the process of getting a small boat underway is a lot simpler than that for getting a big boat underway, you just won’t bother to expend that energy as often with a big boat. With a larger boat, you’ll end up spending a lot more time sitting at your dock or on your mooring.
Start small and use the heck out of your small boat. Only once you feel that you’ve reached the limits of its capabilities, should you start thinking about up-sizing your boat. It’s way better to have a boat that is a little too small for your needs than one that is a little too large. Plenty of people have crossed oceans in boats that were under 30 feet.
There is no reason to buy a new boat. A reasonably well-maintained fiberglass boat will easily outlive its owner. The best used boats are ones kept in cold climates, on freshwater lakes, and that have never been used as full-time liveaboard cruisers. Being in a cold climate means that the boat has been hauled out, winterized, and kept under a cover for about half of its life. Salty seawater is corrosive; so a boat that hasn’t yet been in the ocean will be in better shape for its age (especially its standing rigging, electrical systems, engine, steering system, and keel bolts). Buying a boat that was previously used for just daysailing and part-time coastal cruising is like the proverbial mint-condition used car that was only driven to church on Sundays.
Besides the formal training and certification mentioned above, another thing that insurance companies frequently require of novice boat owners is that you hire a licensed, professional captain to do training sails with you on your boat before they will allow you to operate the boat on your own. Hiring a captain for a couple days is a really good idea, even if your insurance company doesn’t require it. Boats are complicated and idiosyncratic. So it helps to have someone with a lot of experience help you figure out your boat's handling characteristics and walk you through its complex systems.
Your insurance company will also require a report from a licensed marine surveyor. The surveyor will perform a detailed inspection, similar to a home inspection when you purchase a new home. Get the survey before you buy the boat, since you are going to need it for your insurance, anyhow. If the boat has mechanical, structural, or safety problems, it’s better to find out before you own it.
For more on the topic of why you should buy a used boat rather than a new one, and how to go about buying a used boat, see our blog post titled Don’t Buy a New Boat!.
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| Our second boat, a Morgan 22 named Spring Tide. We sailed this boat more than any other boat we've ever owned (even more than the one we currently live aboard fulltime). It was so easy to maintain and easy to get underway, we'd often sail it 3 times a week. Even though it lacked standing headroom, we took it on several multi-day cruises around Sarasota and Tampa Bays. Despite its simplicity, it still taught us a lot about fixing and maintaining boats. Note the rope running over the side and into the water, just aft the dark portlight. The centerboard cable had parted so this rope was holding the centerboard in place. A few days after this photo was taken in the summer of 2004, we hauled the boat out and replaced the cable and hardware. This was the first DIY repair project that we ever did on one of our boats. It was a simple fix but at the time, it seemed pretty daunting. |
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| Janet in the bosun's chair, fixing Fulmar's lazy jacks (Actually, she's fixing Damon's screwup). The work never ends and it's never easy. |
Set Goals
Early in your quest to become a cruiser, begin to develop a long-range plan that includes a series of modest, short- and medium-term sailing goals. This can include things like learning to sail, getting out on X number of different kinds of boats (OPBs), completing certain training courses, or sailing your own boat to a particular destination. Keep the short-term goals modest and achievable, so that you can measure your progress more easily. Don’t solidify your ultimate, long-term goals until you’ve gained some experience, which will help keep your goals realistic. And don’t be afraid to amend your goals as you learn more and develop a better understanding of what is do-able.
Keep your most ambitious, long-term goals a secret, until you actually start to make significant progress toward achieving them. If you start telling your friends and family that you’re going to sail around the world before you’ve even sailed across the harbor, you’re setting yourself up for failure. (But if you plan to cruise as a couple, both partners need to have buy-in and both partners need to share the same goals. Communication with your future crewmates is crucial.)
Your strategic planning should include financial planning and goal-setting. You may need to save a certain amount of money or identify realistic ways to make money as you are cruising. Reality check: don’t expect to be able to make money with a YouTube sailing channel or a blog or by writing for sailing magazines. For every person who has made a living this way, there are thousands who have tried and failed. But if you can work remotely, or if you have a trade skill that is in high demand, you can make money to pay your way as you go. Working remotely is now pretty common so people are familiar with it. But there are also a lot of professions where people can easily find work for short-term gigs: diesel mechanics, carpenters, fiberglass technicians, canvas makers, sailmakers, hospitality workers, and nurses (traveling nurse contracts). Work for a few months then spend the rest of the year cruising.
Look After Your Health & Fitness
Operating and maintaining a cruising boat is physically and mentally demanding. If you lead a sedentary life on shore, you’re going to find life aboard to be challenging. Strength, flexibility, stamina, and balance are all required. And many people who plan to go cruising after retirement don’t ever make it out there because of health reasons. There are plenty of sailors who are still actively cruising into their 80s. But it’s easier to do it when you're younger. The ones who are still able to cruise later in life put effort into maintaining their fitness. You may consider going cruising before retirement age by taking a cruising sabbatical or “pretiring” (taking time off from work with the knowledge that you will probably need to return to work at some point in the future).
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| Boat yoga is a real thing. It's what cruisers call it when you have to cram your body into a tiny, inaccessible space to fix something that has broken. Here, Damon is fixing a bad electrical connection on our engine controls, which are up in the cockpit, above this space. He's laying on top of the refrigerator and stovetop with his feet in the galley sink. He can't fit both arms and his head through the opening into locker space. So he's working over his head by feel. After about 20 minutes of discomfort, the problem was fixed. Just another day in paradise. |
Cruising can be fun and rewarding. It can also pose some personal and financial risks. Whichever path you choose for getting into cruising, you should enter it with your eyes wide open, and you should take a good, long look before you leap into boat ownership. Having a large bank account certainly helps. But that is, by no means, sufficient or even necessary.
We have met a lot of new cruisers over the years, many of whom go on to love living aboard and sailing their boats, and they thrive in their new lifestyle. But a surprising number of fledgling cruisers start out with ambitious dreams, only to abandon them after getting a taste of what life aboard is really like. Sometimes the disillusionment comes from the realization of how much physical effort, mental capacity, and money are required to maintain a cruising boat (even a brand new one). In other cases, the bloom falls off the rose after a traumatic incident, such as running aground in a dangerous inlet, being caught out in a storm, dragging anchor at night, or colliding with another boat. Whatever stressor prompts the soul-searching, having to admit defeat and abandon one’s dreams can cause long-term emotional scarring. These situations usually involve couples. So on top of the trauma, there is often tremendous stress placed on the relationship. In many of these cases, the trauma could have been avoided, or at least mitigated, had the new cruisers been a little more experienced.
The cruising lifestyle should be viewed like a vocation, one that requires extensive training and mentorship, as well as life-long learning. Aspiring cruisers should focus on acquiring knowledge, skills, and experience before focusing on purchasing their ultimate cruising boat.
If you do buy your own boat, help out the newbies coming up behind you. Give aspiring sailors an opportunity to sail on your boat. Remember what it was like for you when you were trying to get into the sailing scene. You’ll also be doing yourself a favor because the best way to really learn a subject is to teach it.
And just remember this: Dumber people than us are out there cruising successfully at this very moment. If they can do it, so can we.
Janet & Damon Gannon started sailing together about 25 years ago. Their current boat, Fulmar, is the 5th boat that they’ve owned together. Damon has a master’s license from the US Coast Guard, with endorsements for sailing and towing vessels. He also used to be certified as a keelboat sailing instructor by US Sailing. He has been sailing and cruising since early childhood and has worked on a variety of vessel types, in a variety of capacities, over the past 4 decades. As part of his job as a research scientist and professor of marine biology, he has trained over a hundred students and research technicians in marine safety, navigation, maritime skills, and small boat handling.
Feel free to contact them if you’d like more specific guidance about learning to sail, searching for a boat to buy, or learning about a boat that you recently purchased.
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| Damon teaching a student how to dock a twin-engine powerboat. |
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