Around the World by Sailboat

How to Find Life-Changing Work and Travel

Article and photos by Andy Schell
Resources updated 5/24/2019 by Transitions Abroad

Sailing fast and hard aboard the yawl Arcturus.

We were heaved-to in the middle of the Atlantic, the sails of the 40-foot sloop set in such a way that the boat drifted slowly through the water, riding gently upon the heaving ocean swell that rose and fell with cosmic regularity. The puffy trade-wind clouds marched across the sky in the perpetual easterly breeze. The sea itself was an indescribable shade of deep blue that exists only in the deep waters far offshore, a color for which we have no word.

I was on the lee deck, wedged between the coach-roof and the lifelines, bracing myself against the swell, gripping an old plastic sextant and practicing my sun sights. Engaging in a method of navigation used for centuries is to truly become one with the universe, a sensation long lost among the lives of those on shore. After plotting my line of position that I obtained by calculating the angle of the sun on the horizon, I reckoned we were around 26 degrees North latitude, 65 degrees West longitude, just about halfway between Charleston, SC and our landfall in the Virgin Islands. We were seven days off the East Coast, another seven or so more to sail, and had finally adjusted to life at sea, the simple life of living in tune with the universe.

Traveling and Working as Volunteer Crew

The author at the helm of the yawl Arcturus.

Amazingly, I was along for this trip of a lifetime as volunteer crew—the owner had paid my way, provided the food onboard, and would pay for a return ticket from Tortola upon our successful delivery of his yacht to the islands, where he planned to use it over the winter months. The boat, a 40-foot, French-built sloop, was incredibly comfortable for the four of us onboard—myself, my father, another 20-something young woman and the volunteer French captain. We had a nice-sized galley with working refrigeration, ample sleeping space, and plenty of food (and coffee) for two weeks at sea.

Traveling the world by sailboat is a dream shared by many but experienced by few—more often than not thrown to the wind and destroyed by careers, commitments, and shore-side attachments. But for those who make the commitment to the sea, the life is incredibly rewarding—universal living, simple in its routines yet profoundly real.

As a lifelong sailor and professional captain, I have traveled the world by every means imaginable, yet have found that the best way to travel is under sail. For those looking for a unique way to see the world and experience life, becoming volunteer crew on yacht deliveries is an exciting, unique, and reasonably affordable way to get around.

Mia Karlsson at the helm of the yawl Arcturus.

How to Find the Right Boat to Work On

Yacht deliveries can range from taking a neglected 32-footer built in the 1960’s from Bermuda to Nova Scotia in the dead of winter (which I have unfortunately experienced), to sailing a sparkling new 70-footer in the warm Trade Winds of the Caribbean, island hopping your way around some of the most beautiful sailing grounds in the world. So it pays to do some research before signing up for any trip that is out there.

Walk to Docks to Find a Boat: Ironically, the best way to get a job as a member of the delivery crew is to arrive in a new port on a sailboat and simply walk the docks looking for work. Unfortunately, the age-old catch-22 situation rears its ugly head—you need experience to be crew, yet need to crew to gain experience. If you are lucky enough to live in a sailing town—such as Annapolis, MD, Ft Lauderdale, FL, or any coastal town in the Caribbean or Mediterranean, walking the docks and talking to people is your best bet at finding a boat. The aforementioned girl on my last trip found our boat in exactly that manner—she was a local from Charleston, SC, simply looking for sailing experience and a ride to the islands where she wanted to pursue her kite surfing passion. Since we were only three at the time, we welcomed her extra help, even though she had never been on a sailboat before.

Use the internet to Find a Boat: If you are like me and come from a rural inland town, or are otherwise far removed from the ocean, the internet is quite useful and provides another means to find a boat. Several websites are dedicated to finding crew, particularly for deliveries, and most are set-up so that you can access them for free. Professional delivery skippers often post ads looking for volunteer crew, and it is often just a matter of sending your resume, a photo and a short email about why you want to crew that will get you on a boat. Oftentimes these skippers are willing to take inexperienced crew as a third or fourth member, and are usually very amenable to teaching.

Take Part in “Cruising Rally’s”: Increasing numbers of retired businessmen and women are buying boats with big dreams of crossing big oceans, yet without the knowledge, skill or confidence to do so alone. Several career sailors have recognized this conundrum and “Cruising Rally’s” are becoming more and more popular in all the oceans of the world. They are organized by experienced sailors with thousands of ocean miles, and together with up to 50 other boats, inexperienced sailors (mostly retirees) can cross the ocean of their dreams in the relative safety of the group, with experienced leadership. Once in port, these newfound ocean sailors have the added benefit of organized parties and events where they can share the joys of their first ocean passage with others.

You can be a part of the increasing popularity of cruising rallies, and many of the organizations behind the logistics maintain websites and crew registers. The Carib 1500, for example, is perhaps the most popular cruising rally on this side of the Atlantic, with close to 50 boats, all over 40-feet (and many much bigger), sailing non-stop from Norfolk, VA to Tortola in the British Virgin Islands. The rally occurs after hurricane season and before the onset of winter, in early November. They also organize a return rally in May, from Tortola to Bermuda. From there, the boats split up and head east to Europe or back to the U.S.

What About Experience?

The author at the helm of the 74' Schooner Woodwind, Pride of Baltimore II in the background.

Many captains, including myself, require at least one if not two professional or very seasoned sailors to join them on a major ocean crossing. However, like me, many are more than willing to take a few extra inexperienced sailors or intrepid adventurers along for the ride and are often willing to instruct them along the way.

The key to finding a boat to sail on is to present yourself as a trustworthy person eager to join the trip. Ulterior motives are often very apparent, and no captain is willing to take along someone just looking for a free ride.

Working Aboard the Sailing Boat

The work aboard an ocean sailing boat is difficult, tiring, and unending. A passage of even 10 days sounds short, yet when you’re on a watch schedule of four hours on, eight hours off, one day seems like two and you must adapt to an utterly different lifestyle than the one you are accustomed to ashore. Everyone shares in all the duties involved in running the boat, from standing watch in the rain at 2 a.m. to cooking breakfast and making coffee. Then you must clean up upon arrival when the boat is in shambles and you have not had a freshwater shower in two weeks.

Life at sea is incredibly raw and incredibly basic. Your world shrinks to the three miles or so you can see in every direction before the horizon curves out of view. A passing freighter is often the most exciting thing to happen on a given day. The intense discomfort of being salty and sticky for two weeks is offset by the rewards of a cloudless night watch under a new moon. The sky is so dark you can scarcely see your hand in front of your face, yet the stars fill the night sky all the way to the horizon, like an enormous diamond exploding in the center of the universe, sending fragments to every corner of space. You will see more shooting stars on one night watch then you would in a lifetime ashore; at sea, the lights of civilization do not pollute the sky.

Ocean Sailing Makes the World Feel Big Again

In our age of instant communication and light-speed travel, crossing even a short distance in a sailboat reminds us that despite our attempts to shrink the world with technology, our planet remains one enormous place. After two weeks at sea, watching a distant island grow on the horizon provides an indescribable feeling of accomplishment. The first beer ashore never tasted better, and a freshwater shower after weeks of bathing in the salty ocean is a blessing from Heaven.

If you plan accordingly and have ample time, traveling the globe by “hitchhiking” on sailing yachts is a truly unique and rewarding way to see the world. After the first trip, you are no longer inexperienced and it becomes progressively easier to find and sail on additional boats. You will save thousands on airfare and gain a greater appreciation for the distances we travel so quickly through the sky. But most importantly, you will return to nature, experience life with a stronger sense of connection to the universe, and return with unforgettable stories. You will be changed.

Andy Schell is a professional captain and freelance writer who lives aboard his sailboat Arcturus in Annapolis, MD and travels extensively.