Effortless broad reaching, a dip in refreshing waters, cocktails in the cockpit, reunions with family and friends, a chance to learn a new onboard skill — those are the reasons vacation sailors say they return year after year to their bareboat company of choice.
But why do the owners and operators of these companies do it? Aside from the obvious reason — it’s a way to earn a living — running a charter company isn’t magic. It’s work. Or, “a labor of love,” as one put it.
A roundup of a dozen successful small bareboat charter companies, some of them family-owned and in business for decades, reveals why they got in and how they stay in the game. Companies also explain how their approach helps them shape and prioritize their business goals, and what the challenges are, as well as the opportunities — from operating in the virtual sphere of digital technology to minding the fleet in the flesh by walking the docks and sending sailors out in divergent, if gorgeous, cruising grounds.
Origins/motives/genesis Fresh from careers in hotel management and banking, Cindy Chestnut and Brian Gandey knew what they sought when they started Conch Charters at Fort Burt Marina on the island of Tortola, in the British Virgin Islands, in 1987.
“We always wanted to be a small company,” Chestnut says. “And it was also a conscious choice to locate Conch Charters at a sailor’s marina rather than a fancy marina. We went for a location that allowed us to pass the savings on to our customers. And our customers seem to appreciate that more than having a swimming pool.”
What Gandey and Chestnut carried out, parlaying skills learned in one industry to do well in another, also worked for others.
Merion and Jennifer Martin run a mixed fleet of 25 power- and sailboats
A roundup of a dozen successful small bareboat charter companies, some of them family-owned and in business for decades, reveals why they got in and how they stay in the game. BY ELAINE LEMBO
at Desolation Sound Yacht Charters in Comox, British Columbia, Canada. “Having worked in the superyacht industry in Europe and the Caribbean charter circuit for years has given us the experience to know what people expect and how to exceed their expectations,” Jennifer says.
Dave Conrad, of Great Lakes Sailing Co. in Traverse City, Michigan, says he and his wife, Kristen, met while he was managing a charter base in the Caribbean. Together, the couple worked aboard crewed yachts before buying the Traverse City 20-strong fleet of sail- and powerboats.
“Our success is a direct result of our hands-on approach to running the company,” Conrad says. “In the early days, we had little to no staff. We commissioned over 20 boats every year. We painted every bottom, did all the rigging, repairs and maintenance, and answered every phone call ourselves. We worked boat shows together even when Kristen was eight months pregnant.”
Some sailors got into the business so they could immerse themselves in a beloved pastime. “We started 40 years ago with one boat, as a way to help pay for it,” says Roger Van Dyken, of San Juan Sailing in Bellingham, Washington. “It turned into a hobby, then a pleasurable activity, and then, when we formed the business, it became an enjoyable enterprise.”
As Patti Gonsalves, of Cruise Abaco in the Bahamas, puts it, “We started the company with our own personal boat, grew to three, and just kept growing.”
For Brian Blank, of Newport, Rhode Island, this “labor of love” arose from a brush with America’s Cup fame. “I was working a summer job in 1977 at Bannister’s Wharf and became part of the dock crew for Ted Turner and Courageous,” Blank recalls. “Most fun I’ve ever had! I guess I just fell into the boating lifestyle and adventures. I ended up buying my first 38-foot sailboat for charter in 1985 and have never looked back!” His Bareboat Sailing Charters 15-member fleet floats on moorings in Brenton Cove, in Newport Harbor. Know Your Niche, and Set Priorities Serendipity didn’t play a major role in Kurt Jerman’s business plans when he opened the charter portion of West Coast Multihulls in 2011 in San Diego, but understanding the market did.
“There have always been plenty of schools and charter locations in the Southeastern United States, the Bahamas and the Caribbean,” he says. “The key for us has been to fill a void in the market here on the West Coast with catamaran instruction and charters.”
A few local sailing clubs dabbled in catamarans, Jerman says, “but none really knew that much about the boats, or the catamaran business as a whole. As a retail outlet for multiple catamaran manufacturers, my company had been importing cats to the West Coast since 1999.”
With an emphasis on teaching and certifying aspiring cat sailors, the business has gone from a two-boat, one-base center to a 10-boat, two-base concern, with a fleet of 10 privately owned cats from 35 to 58 feet in length. The new base, opened in high season 2018, is at Puerto Escondido, in the city of Loreto, Baja California Sur, Mexico, off the Sea of Cortez.
If charter is the “try before you buy” gateway to informed ownership, West Coast Multihulls has a fraternal East Coast twin. Over 25 years in existence, Maine Cat, of Bremen, Maine, has built 140 of its fast, light sail and power catamaran models in a range of lengths to an enthusiastic clientele. Its focus is on boatbuilding and direct sales to customers.
“When people say, ‘Let’s go charter a boat,’ Maine Cat is not the first company that comes to mind,” says owner Dick Vermeulen. “If you want to go sailing, we’re not the typical charter boat — our cats are performance cruisers.
“Our focus is not chartering. Having said that, our base in the Bahamas allows people to try one of our models and see if they like it.” The company’s base in Abaco, Bahamas, and its one-cat charter availability from Rockland, Maine, are live showrooms, and typically fully booked.
While charter is a valid means for sailors and aspiring sailors to transition to ownership, the critical stage of instruction can’t be overlooked, and that too has long been an ingredient of the recipe for success for West Coast Multihulls, Maine Cat and countless other charter outfits. Schools offer certification through custom curriculums or through organizations such as the American Sailing Association and US Sailing.
“We have been an ASA school since 1985 — one of the oldest still around,” says Barb Hansen, of Southwest Florida Yachts. “We see even more of a need for instruction now as the baby boomers get close to retirement. They now have the means to buy a boat, but might not have the skills.”
And Hansen, faced with countless aspiring owners, feels obligated to assess their needs. “When people come and ask me to help them find a boat to buy, I ask them what their experience is,” she says. “If they have none, I strongly suggest they go through our classes first. I tell them, ‘I would be happy to sell you a boat, but you would be buying a boat without the proper knowledge or experience.’ As with anything else, an informed buyer is going to be a better owner.”
Other companies, such as South Coast Sailing Adventures in Kemah, Texas, near Galveston Bay, remain dedicated and focused on instruction. “Our sailing school is the core of our business,” says owner Lucy Newman. “We strive to train competent and knowledgeable sailors, with a focus on safety and courtesy, while still having fun. We strongly believe that safe boating is achieved through education.”
With a view to longevity, Cindy Kalow, of Superior Charters in Bayfield, Wisconsin, adds, “Instruction is now paramount to our ability to maintain a fresh customer base and create future sailors. We would not still be in business if we didn’t have a training/certification arm to our business.”
Challenges and Opportunities
Fleet maturity is a challenge that some smaller charter companies have had to deal with, and some have had an unprecedented hurricane season transform their business plan.
“The image of us having older boats is one we’ve been working hard to alter; our oldest boats are now 7 or 8 years old,” says Chestnut, of Conch Charters, of a fleet that grew to 56 a few years back. “Of course, hurricanes Irma and Maria in
September 2017 affected that.”
As Conch rallied to get under way in time for charters in high season 2018 with a dozen boats, Chestnut says, “We never anticipated that we’d be at this juncture at this point. We want to continue to rebuild — it’s Conch Charters. It’s our baby. We don’t want to see it go poof! We’re coming back.”
Mother Nature isn’t the only force at play. “The market has changed,” says Kalow. “People no longer participate in just a few hobbies or activities. In the past, people would label themselves a sailor or a golfer. Our younger customer base is very active and has a lot of interests. We continually work to tap into new markets and customers who are looking for new and different experiences. You have to keep your product fresh, understand what you offer and stay sharp on how you present that offering.” Then there’s the effort you put out. “We have worked our tails off for nearly 35 years,” says Hansen. “I’m still here seven days (and nights) a week, with the occasional day off. If you don’t have that passion for your business, then you won’t succeed. You have to believe in what you do and then try to do the best job you can do.”
Rapid advances in digital technology have also had a major impact, and present new possibilities. “The sharing economy has opened up people’s eyes to unique lodging opportunities, and being based in San Diego makes it easy for us to offer Cruise-n-snooze charter stays on the boat, like Airbnb on the water with a sunset cruise thrown in,” Jerman says. “That might have been hard to explain before, but now people just get it.”
Adds Chestnut, “People are more easily reached and found. Our reservation system is online. We put an e-tablet on each boat with the chart briefing and all charts and a nav system, as well as fun facts like plants and fish they might encounter. We have a checklist of each yacht’s systems. If charterers have a problem while they’re out, they can take a picture and send it to us via a text or email.”
It’s Magic — or Is It?
Company owners enjoy describing the ineffable twist to attracting repeat clientele.
“We retrieve lost luggage and deliver it, grab the bag of ice they forgot, pick up their trash on the water if they missed the drop-off in a settlement,” says Gonsalves, of Cruise Abaco. “When the owner of the company is the one who you see on the dock and on the water, you know you’re being taken care of. No request is impossible!”
“We make sure the client gets what he or she paid for — a fantastic time on the water,” Jerman says. “There’s a risk in making things overcomplicated.”
Resilience in the face of setbacks such as hurricanes also scores big with sailors. “At the end of the day, it’s all about attention to detail and giving people a little bit more than they expect — a beach bag, a bottle of rum,” says Chestnut. “One client has been chartering with us for 27 years for two weeks a year. They ask us if they can bring anything down. They’ve brought us starter motors for cars, maple syrup. That’s what makes our company nice. It’s like a family.”
It helps that, by and large, a charter trip is a happy experience. “Our customers are on vacation!” Hansen says. “It’s not like they are going in for a root canal. We love that we are often fulfilling a dream for someone or we are helping them plan the trip of a lifetime!”
It works at San Juan Sailing too. “Our staff derives sheer joy from helping people have joy — period,” Van Dyken says. “Nothing beats passionate, selfless service.”
Blank, of Bareboat Sailing, sticks to this philosophy: “Keep your customers happy, and they will always come back.”
I roll off the cockpit settee, pop my head over the dodger and look into the night. Twenty degrees off our starboard bow, I do see it: three white lights in a vertical line, then a red light below and to the left of the others. “I’ve been watching him for a while,” Hank says. “His bearing hasn’t changed.” My first reaction is to call for an exaggerated turn to port. As I try to shake off sleep, an exam question flickers from some dim recess.
You are approaching another vessel at night. You can see both red and green sidelights and, above the level of the sidelights, three white lights in a vertical line. The vessel may be ___________ . a. not under command b. towing a tow more than 200 meters astern c. trawling d. underway and dredging
My heart races before I call for the course change; another question runs through my mind.
You are aboard the give-way vessel in a crossing situation. Which of the following should you NOT do in obeying the Navigation Rules? a. cross ahead of the stand-on vessel b. make a large course change to starboard c. slow your vessel d. back your vessel Adrenaline wallops me. “Turn 90 degrees to starboard,” I say. For the next minute or so, the tug moves safely across our port side, and soon we both see the faint red sidelight of its barge some hundreds of yards behind. I think of the hawser connecting them, lethal and invisible, then sit chatting with Hank for a few minutes before lying back down for another 20-minute nap. (For the record, the correct answers are B and A.)
HANDS - ON SAILORS
I’ve joined Shawn Brown and Hank Schmidt as their instructor for a pair of courses — Coastal Navigation and Coastal Passage Making — two intermediate steps in a tiered curriculum from novice to expert that’s created and administered by the United States Sailing Association, or US Sailing (ussailing.org). Shawn is an airplane pilot who’s recently left a tech startup and is now looking to buy a 50-something-foot ketch to live and cruise aboard. Hank (no relation to the Hank Schmitt who organizes cruising rallies under the Offshore Passage Opportunities name) is a New York City emergency-room physician who hopes to start crewing on ocean-sailing trips from the U.S. East Coast to the Caribbean. Both would like to charter sailboats in different places around the world. If they can successfully perform the hands-on tasks laid out in each course and pass the written exams, they’ll receive US Sailing certificates that demonstrate to charter companies and skippers that they’ve attained a rigorous level of proficiency in these disciplines.
For this trip, we’re sailing Matilda,a newish Hanse 505 managed by New England Sailing Center in Newport, Rhode Island. The Coastal Passage Making curriculum includes night passages, so we plot a track that will take us from Narragansett Bay out to Shelter Island at the eastern end of Long Island, then across Block Island Sound to Martha’s Vineyard, before returning to Newport — a triangle of some 200 miles over five days, including two overnighters.
After stowing provisions and getting familiar with the boat’s systems, we work through this question together:
The Hanse 505 is fitted with a Volvo D2 diesel engine and 75 gallons of fuel. If she cruises at 6.5 knots and burns 1.75 gallons per hour at 2,200 rpm, what is Matilda’s safe cruising range under power? a. 75 miles b. 175 miles c. 275 miles d. 375 miles It takes two steps to answer the question. We know that the engine burns 1.75 gallons per hour and that Matilda will travel a distance of 6.5 miles in one hour. Our first step is to figure out how far we’ll travel on a gallon of fuel. Dividing 6.5 miles by 1.75 gallons gives the answer: 3.71 miles per gallon.
Next, we need to know how far our tank of fuel will carry us. Multiplying 75 gallons by 3.71 miles per gallon gives a result of 278 miles. Answer C, 275 miles, is mathematically possible but not a safe cruising range. Applying a safety factor of 25 percent leaves us with a range of 208 miles. The answer B, 175 miles, leaves us a safety factor closer to a third of a tank. B is the best answer to this question. In practical terms, this means that even if the wind shuts off all week, we could still complete our itinerary without refueling.
We spend our first afternoon sailing in Narragansett Bay, calculating time-speeddistance problems and plotting courseto-steer vectors through the tidal current as we reach over the top of Conanicut Island, then tack down the West Passage to Dutch Harbor. Shawn and Hank study the chart and select a spot near the mouth of Great Creek that shows 14 feet of depth at mean low water and is marked with an “M” for its mud bottom. Calculating for 7-to-1 scope and taking into account the tidal range and our 5 feet of freeboard, they set the hook, then put out 160 feet of rode. We grill chicken, share a few laughs and turn in early.
Our trip’s first night passage begins at 0200.
FROM LUBBER TO SALT , STEP BY STEP
US Sailing, which has existed in one form or another for more than 120 years, describes itself as “the national governing body for the sport of sailing.” In the 1980s, it got into the business of teaching sailing, with an initial focus on kids and small boats. In the 1990s, it began developing courses for adult sailors in bigger boats — “keelboats,” as opposed to dinghies, and cruising in addition to
racing. Similar instructional programs are available that lead to American Sailing Association certification (see “ASA Courses and Certifications,” page 40).
Two years ago, US Sailing reorganized itself to simplify its several missions. Now there’s a dedicated Youth department, which focuses on teaching kids to sail small boats through local sailing schools, yacht clubs and community sailing centers. Its Youth network includes some 1,500 instructors. Other US Sailing departments support sailboat racing up to the Olympic level, providing rules, coaching, measurements and other tools to create a level competitive playing field.
The courses Shawn and Hank are taking fall under US Sailing’s Adult department. Since January 2017, that division has been led by Betsy Alison, a champion in several senses of the word. Five-time winner of the Women’s Keelboat Championships, five-time Rolex Yachtswoman of the Year and 2011 National Sailing Hall of Fame inductee, her competitive record speaks for itself. But in a broader sense, Betsy has long
been a champion of providing people access to the water, especially folks with clear barriers. In 2015, she won the ISAF World Sailing President’s Development Award for her work as head coach of the US Paralympic Sailing Program.
In her new role, Betsy’s mission has broadened. “We just want to get butts in boats,” she told me last winter. “We want people to try sailing and have a hands-on experiential learning opportunity that hopefully sparks their interest and makes them want to continue.”
For Betsy and her department, that mission starts with a program called First Sail (ussailing.org/education/adult/firstsail). First Sail sessions typically run two hours and cost between $35 and $100 per person; after that, many clubs or schools offer discounts on future lessons. “We have First Sail locations that are not US Sailing keelboat schools or yacht clubs,” Betsy said. “And we don’t mind whether someone is using ASA instructors or volunteer instructors or whatnot. It’s the first entry point in my department, and it’s for people who have never tried sailing before.”
The next step for folks who want to learn more is US Sailing’s Adult Keelboat program — and this is the track Shawn and Hank are following. The US Sailing website includes a list of accredited schools that offer certification (ussailing .org/education/adult/certification-coursesendorsements/find-a-school). With about 75 schools on the list, that network is smaller than what you’ll find with US Sailing’s Youth program (1,500 instructors) or the American Sailing Association (roughly 300 schools and clubs).
The Adult Cruising Track lays out a progressive set of standardized stepping stones to lead novices toward sailing expertise: Basic Keelboat Basic Cruising Bareboat Cruising Cruising Catamaran Endorsement Coastal Navigation Coastal Passage Making Celestial Navigation Offshore Passage Making In addition to these, US Sailing offers other targeted programs, including Safety at Sea courses and a host of online instruction. “If you look at the millennial generation,” Betsy said, “they don’t want to own things. They want to go to a community sailing program or to a sharedboat club and lease or charter a boat and enjoy it without having to make the big financial investment in it. So this year we’ve started expanding our small keelboat program.” For such people, certifications are their ticket to renting boats. So, US Sailing expanded its program last year to include Performance Keelboat. “It’s an opportunity to teach people to sail their boats better and faster without being related to racing.” It’s also unrelated to the more systems-heavy cruising track.
Another new course comes under the heading of US Powerboating. “What sets us apart from some of the other powerboat-instruction providers is that our programs are all focused around hands-on, experiential learning,” Betsy said. “So you learn how to pivot-turn; you learn how to dock and undock, and all the little nuances that you don’t get if you sit online for your boater’s education card.”
BRINGING IT ALL HOME
The full reality of that hands-on, experiential instruction hits us at 0130, when wakeup alarms start ringing through Matilda’s cabin. After that initial jolt, only the clatter of the anchor chain breaks the midnight silence as we hoist the main and sail off our anchor engineless. A gentle southerly and the ebbing current take us quietly out past the Dutch Harbor mooring field and back toward West Passage.
“See that red light that’s flashing twice then once every six seconds?” I say to Shawn. “Keep that just off our starboard bow.” This is the preferred-channel buoy “DI” at the south end of Dutch Island — red on top, green on the bottom, with a composite group-flash light pattern at night. We talk about how boats traveling north up the West Passage treat this navigation aid as a red mark if they intend to continue up the main channel but as a green mark if they’re going up the secondary channel into Dutch Harbor. When Shawn and Hank take their exam at the end of the week, they’ll remember this moment; at least five questions deal with aids to navigation, and more than one of those asks about preferred-channel buoys.
With sunrise off Point Judith comes the New England fog — the “smoky sou’wester,” as advection fog is known in these parts, recognizing the strange pairing of zero visibility with a ripping breeze. What should we do?
Shawn combs through the Navigation Rules to find out. Subpart D covers “Sound and Light Signals.” Rule 35 treats “Sound Signals in Restricted Visibility.” That’s us. “In or near an area of restricted visibility, whether by day or night,” he reads, “a power-driven vessel making way through the water shall sound at intervals of not more than two minutes, one prolonged blast.” Elsewhere we read that a prolonged
blast sounds for four to six seconds. Sure enough, we can hear one of those off our port beam — and it’s getting louder. But that signal is for power-driven vessels, and we’re sailing with our engine off. What about us? “A vessel not under command; a vessel restricted in her ability to maneuver, whether underway or at anchor; a sailing vessel; a vessel engaged in fishing, whether underway or at anchor; and a vessel engaged in towing or pushing another vessel shall … sound at intervals of not more than two minutes, three blasts in succession, namely, one prolonged followed by two short blasts.” And so for the next three-quarters of an hour till the fog clears, we take turns blowing the air horn — one prolonged, two short blasts, every two minutes. The sound of the other boat moves aft, but we never catch sight of it.
Through the morning and the early afternoon, we devise a watch schedule to make up for last night’s short nap, and we set up a detailed log of our progress. All day we motor sail a little south of west toward Gardiners Point, keeping a close eye on the weather. The NOAA forecast calls for a powerful front arriving later and bringing gale-force winds through the night. We call up National Oceanic and Atmospheric Administration’s graphic marine weather charts (nws.noaa.gov/om/marine/home .htm) and compare the surface analysis with the 12-, 24- and 48-hour forecasts. We talk about the isobars, those lines of equal barometric pressure on the map, and how tighter isobars indicate greater wind velocities. We talk about the changing sky, and what the progress from cirrus to stratus to cumulus foretells. Later that night, safely anchored in Shelter Island’s Coecles Harbor, the shrieks through the rigging and the boat’s snappy pitch send home the message that what we’re learning here isn’t just theoretical.
The gale doesn’t quite blow itself out till early afternoon, so we use the next day for coursework at anchor: tide problems using the rule of twelfths, set-and-drift plots, safety procedures in cases of fire or crew overboard. We use the time to plot a current-corrected course back across Block Island Sound to Martha’s Vineyard. After a swim and a late lunch, we up anchor and set off in time to round Gardiners Point by sunset and begin our second overnight passage.
By the time we return to Newport after five days out, the exam questions for the Coastal Passage Making certification seem a little less daunting — and a little more real.
The greater the pressure difference between a high- and low-pressure center, the: a. cooler the temperature will be b. drier the air mass will be c. warmer the temperature will be d. greater the force of the wind will be Fog formed by moisture-laden air moving across a cold portion of Earth’s surface and condensing is called: a. sea fog b. radiation fog c. advection fog d. frontal fog A lighted preferred-channel buoy will show a: a. Morse (A) white light b. composite group flashing light c. yellow light d. fixed red light To pass the course and gain their
THE CASE AGAINST CERTIFICATION
In addition to the excellent sailing schools you can find through the ASA or US Sailing networks, you might also want to explore some of the one-off courses that offer guided sailing experience but without standardized certification.
Two occasional CW authors, Teresa Carey and John Kretschmer, each run individualized offshore sail-training programs, and there are plenty of others.
Carey and Ben Eriksen lead Morse Alpha Sail Training (morsealpha.com) aboard their Robert Perry-designed Norseman 447. Together, they have 25 years of experience in sail training, wilderness medicine and Outward Bound education. Both are U.S. Coast Guard-licensed masters.
“The great thing about organizations like ASA and US Sailing is that there are standards of quality and curriculum on which students can rely,” Carey writes on her blog. “If you choose to go with an independent organization like ours, you draw more of a wild card. You have to do your own research to know if you will be receiving quality instruction from an experienced sailor.” What’s the case against certification? According to Carey, it’s the cost, the limiting curriculum and the lack of obvious benefits. “Each student makes progress at different levels,” Carey says. “And not everyone fits well into a predetermined program. Additionally, if a student’s ability surpasses the prescribed curriculum, we are prepared to offer them a more challenging expedition.” Charter companies and insurance providers, she argues, care more about experience than certification.
At press time, Kretschmer (yayablues.com) was leading a group of students across the North Atlantic to the Azores. “When my sailing odometer ticked over 300,000 miles, I stopped counting,” Kretschmer wrote. His personalized sail-training programs offer students a chance to glean some of that experience.
“Our Offshore Training passages are unique,” Kretschmer says. “And so are the people who find their way aboard. I am not a sailing school; there are plenty of those around, and many do a fine job of teaching offshore sailing skills. What we do is different. We make passages; we make voyages. They’re real, sometimes all too real. Each passage is composed of crewmembers with varying levels of experience, and we learn from each other.”
A quick online search will turn up other individualized programs — or “wild cards,” as Carey says. certification, Shawn and Hank need to answer at least 80 percent of these questions correctly (the answers to the questions above are D, C and B, respectively). That’s 64 out of 80. But after this week, all that theory from the textbook has been fleshed out with a boatload of indelible memories. All that said, this story has a happy ending: They passed.
CW editor at large Tim Murphy holds a 100ton Master’s license and has taught sailing for many years. He’s preparing a 1988 Passport 40, Billy Pilgrim, for long-distance voyaging.
The San Juan Sailing fleet rafted up at the Octopus Islands marine park during a guided flotilla cruise of the San Juan and Gulf islands.
Maine Cat Charters (top) offers a great opportunity not just for a vacation, but also for prospective owners to try the boat out before buying. Brian Gandey and Cindy Chestnut started Conch Charters in 1987.
West Coast Multihulls hosts an annual fun rally to Catalina Island (above). Mark Gonsalves, owner of Cruise Abaco, smiles with customers (right). A Jeanneau from Desolation Sound Yacht Charters rests in a picturesque anchorage.
Matilda’s crew (from top): airline pilot Shawn Brown, instructor Tim Murphy and physician Hank Schmidt.
After our first good day of sailing, the hook was down in Dutch Harbor off Conanicut Island just in time for a memorable sunset.
Anchored off Shelter Island, we waited for the gale (top). The following day was ideal for cockpit coursework.