Not Just a Dream


From rookie to veteran, how to learn the cruising life  (published March 2013)

Cruising on a sailboat isn’t rocket science. Sure, there is a lot to know but that doesn’t mean the dream of sailing over the horizon is unattainable. The thing is, cruising sailors tend to be natural learners. When focused on a goal, we soak up information and make educated decisions based on our own experience and that of our peers. The question then becomes, if I have the cruising dream, where do I start in making it a reality?

When learning to cruise on a sailboat one thing has to be understood from the start—there is a distinct difference between learning to sail and learning to cruise. Agreed, learning to sail is part of cruising, but cruising is more than just tacking, jibing, points of sail and being able to maneuver a boat to and from a dock.

Cruising is about seamanship, with the ability to manage a vessel and its crew offshore, inshore and in conditions that may be less than desirable. Plenty of sailors dream of making landfalls at pristine beaches or under majestic mountains but may not know how to convert that dream into reality by mastering the basics of sailing, seamanship, navigation and the host of skills needed to run an offshore quality sailboat. So, here’s the way to learn how to lead the cruising life.

Most people who want to learn how to cruise on a sailboat have had their interest sparked at some point or another. Maybe it was while sitting on a beach watching a sailboat crossing the horizon or from sea stories told by a friend or relative who has done some cruising. Whatever the motivation, there are a number of ways to take yourself from novice to full-fledged passagemaker, no matter where you fall on the cruising spectrum.

In teaching cruising and navigation, I have found there are basically three types of students who come in with the passion and enthusiasm invoked by the dream of cruising on a sailboat:

1) The Rookie is a complete novice who has very little technical knowledge of sailing, but has been bitten by the dream of cruising and wants to charter in a tropical locale or possibly take the plunge into boat ownership and full-time cruising.The Rookie may not necessarily want to cross an ocean, but he at least wants to do some coastal cruising or island-hopping at his own pace.

2) The Intermediate will generally know a fair amount about how to operate a sailboat, she could charter a small boat for a day with family or friends and might have crewed in some races or on a coastal cruise. This is the sailor who has just enough experience to capture the sailing dream in a relatively short time and will go to great lengths in her educational endeavors to do so. The Intermediates tend to learn very quickly as they already have a solid grasp of many cruising concepts and are helpful, enthusiastic crewmembers.

3) The Veteran is the sailor who has sailed for many years—often from an early age—and has acted as crew, made an extended passage or taken a few charters, is capable of standing a night watch and could probably take over if the skipper became incapacitated at sea. Generally, The Veteran has enough knowledge to know he needs just a bit more blue water experience if he wants to safely set out across great expanses of ocean on his own vessel.

The one common thread all these sailors share is that they need real life cruising experience in order to learn the ropes and gain confidence in their ability to sail offshore. So, what does each of these sailors need to accomplish in order to fulfill their individual cruising dreams? What do they need to learn and what are the important things they need to understand before taking off over the horizon?

If you are completely new to sailing or have very little practical sailing knowledge, start by taking a beginner sailing course and work your way up through the school’s various levels (See “Back to School, A guide to Choosing a Sailing School”, in the August 2012 issue of BWS). Look for a sailing club or school that will start you in smaller boats and then help you work up to handling larger cruising boats that are capable of going on overnight or weekend cruises.

IMG_0170   Master the sailing skills you’ve learned and get a handle on basic navigational techniques, weather information, anchoring and general boat maintenance. Remember, you are just starting out, so take it slow and learn at your own pace. This is also the time to start reading up on all things cruising. Books about seamanship and choosing and outfitting a cruising sailboat will help you learn the language of sailing, which will help as you gain more experience.

Don’t cringe, but you should also think about racing. I am well aware that sailboat racing may be counter to what the cruising life is about, but it can really help hone your sailing skills and enhance your overall comfort on the water. Plus, you will be around other sailors who can plug you into future sailing opportunities.

A common mistake made by The Rookie is to think too big too fast. I had a student on the first day of a learn-to-sail class tell me that within a year she was going to the Med to buy a boat and start an extended cruise. I thought it was a tad ambitious but figured she would learn what boat ownership and cruising entailed as she went through the classes. Sure enough, about a month later, I had her as a student in a cruising class and she said, “Wow, I’ve definitely changed my timeline a bit. I didn’t realize how much goes into actually making this happen.”

At this point, you have taken some classes or achieved a reasonable amount of experience on your own. To really get the finer points of what it means to live and cruise on a sailboat, ask yourself some questions: How many nights have you spent on a boat at anchor? Have you sailed in reasonably heavy weather and at night? Can you proficiently navigate with paper charts and electronics?

If you can answer these questions in the affirmative, you are probably ready to tackle a true offshore experience. Find a cruising rally and ask if anyone is in need of crew, ask sailing schools if they need help delivering boats or better yet, find a school that offers an authentic blue water experience that will allow you to learn along the way. Also, attend a boat show that offers cruising seminars and learn from people who have done what you want to accomplish. Plus, boat shows are great opportunities for networking, as you will be around likeminded people who are equally enthusiastic about cruising.

Once, while giving an Intermediate a debrief after a week long cruising course, I told him that he was on track knowledge-wise, but if he wanted to buy a boat and start cruising he needed more practical experience. So he started doing deliveries as crew and within a year, sent me a link to his blog and a photo of himself swinging in a hammock strung between the mast and forestay of his own boat in the Bahamas.

All right, you’ve been to the seminars, read all the books, taken the sailing courses and might even own a boat that you are preparing to take offshore. Now what? Now is the time to gain more experience and refine your sailing knowledge. Keep looking for offshore opportunities on other boats or get out and do short trips on your own. You will learn a lot by being out in real time with other sailors or about the workings of a well equipped offshore boat.

Self-sufficiency is crucial to being a successful cruiser, so think about aspects of the cruising life that you will have to do on your own once you have sailed over the horizon. Look for courses on diesel engine maintenance, navigational (GPS, radar, AIS and celestial navigation),  rigging and sail repair, wilderness medicine and weather courses that not only teach you about weather, but how to obtain and use weather information while offshore.

I’ve taught veterans in advanced offshore classes who were well suited to leave on a cruise any day and others who probably needed more experience. The common theme at this stage is that students know their limits and you will too. When you do a real offshore passage, you’ll learn a lot about where your strengths are and what you need to learn for the future.

The reality of cruising is that you are never going to feel as prepared as you should, and the hardest part is to stop outfitting the boat, taking classes, reading books and doing maintenance. At some point, you need to be comfortable enough to cut the dock lines and sail away. Take it slowly at first, though. We have all seen and heard horror stories of people getting overzealous, jumping off the dock into a major ocean passage on what is essentially a shakedown cruise and they either turn back in misery or agonize through the passage, only to end up at their destination in disarray, which can make for a quick end to the cruising dream.

No matter what your experience level, if you have the dream to go cruising, it is attainable. And, there are plenty of good resources available in the way of books, classes, seminars and crew opportunities that will give you the realities of the cruising life while helping you achieve your goals.

Where to Learn?

U.S. Sailing
The governing body of the sport of sailing in the United States, U.S. Sailing has a series
of sailing courses tailored to take you from novice to offshore sailor with ease.
Basic Keelboat
Basic Cruising
Bareboat Cruising
Coastal Navigation
Coastal Passage Making
Celestial Navigation
Offshore Passage Making
Flotillas (offered by Certified Schools)
Sailing Clubs
For more information or to find a U.S. Sailing certified school visit

American Sailing Association (ASA)
Taking you through eight levels of instruction, ASA sailing programs focus on a wide range of sailing skills designed to help you achieve your specific sailing goals.
ASA 101, Basic Keelboat Sailing
ASA 103, Basic Coastal Cruising
ASA 104, Bareboat Chartering
ASA 105, Coastal Navigation
ASA 106, Advanced Coastal Cruising
ASA 107, Celestial Navigation
ASA 108, Offshore Passagemaking
ASA 114, Cruising Catamaran
Sailing Clubs
For more information or to find a school visit

Mahina Expeditions
John Neal and Amanda Swan Neal offer one-of-a-kind ocean passagemaking instruction aboard MahinaTiare III, their Hallberg-Rassy 46. As your expedition leaders, John and Amanda will guide you through all facets of cruising and passagemaking that will take your learning to a whole new level in locations throughout the world. Not able to join them for a sailing expedition? No worries, they conduct seminars throughout the U.S. and John’s consultation services can help you select a cruising boat or plan your next cruise.
For more information on sailing with John and Amanda visit

John Kretchmer Sailing
John has been sailing professionally for 30 years and has logged more than 300,000 offshore miles. Aboard his 47 foot sloop Quetzal, he invites paying guests to join him as he roams the North Atlantic, Caribbean, Med and even the Pacific. Along the way, John will teach you all about sailing and the sea.
For more information visit his website

Two Can Sail
Jeff Grossman and Jean Levine run couples seminars and onboard training sessions. Their focus is on cruising as a couple and they can take you from the first steps of buying a boat—they are surveyors, too—to the fine points of passagemaking. And, they teach you on your own boat.
For more on Two Can Sail log on to