Great Escape

10 Tips for Chartering Nirvana

1. Designate a captain. Sometimes, situations arise where decisions have to be made and executed quickly for the safety of all on board. Having one person in charge will help in this regard should the feces hit the rotary oscillator, so to speak.

2. Pay attention during your charter orientation and don’t be afraid to ask plenty of questions—even the “dumb” ones.

3. Conduct daily engine, fuel, water, and any other checks recommended by the charter company.

4. Always have alternative destinations identified should you need a quick detour to safe harbor or anchorage.

5. Don’t be afraid to stay in port during threatening weather, even if it means throwing off your itinerary. It’s always better to be stuck in port wishing you were out cruising, than cruising and wishing you were in port.

6. Always have a means of communicating with family and friends back home. It provides peace of mind for everyone involved and is crucial in the event of an emergency (at your end or theirs).

7. Never approach a dock faster than you want to hit it.

8. Keep an eye out for deals and freebies. Purchasing meals, fuel or supplies may get you a comped night’s mooring, free trash disposal, or complimentary use of pools and other amenities.

9. Try a one-way charter to extend the range of your cruising vacation. It may cost a bit more, but it keeps you from back-tracking past areas you’ve already visited.

10. Consider purchasing trip cancellation insurance. It safeguards your deposit should you miss your booking date for any number of reasons (health issues, cancelled or delayed flights, inclement weather, etc.).

Resources

Great Escape

By Heather Steinberger
When the Great Lakes ice over, charters in exotic locales — like the BVI — provide the perfect getaway.

The moment of truth had arrived. Anne-Marie stood on the dock, smiling. “Don’t worry, you can do it,” she said encouragingly. “Remember, it’s a right-handed prop, so it’s going to pull to port.”

I looked at the tight confines of the marina. If we reversed out of the slip to port, we’d be heading toward shore and would have to execute a precise “back-and-fill” to get out. We’d practiced this several times in North Sound—give the single-engine Beneteau 403 some forward throttle, turn her hard over, then put her in reverse to make a tidy U-turn. Yet that had been with imaginary boundaries. At the moment, I was staring at yachts on moorings, the dock across the way and a formidable concrete retaining wall.

Teresa announced the docklines were free and gave me the thumbs-up. The wind piped across our starboard rail, toward the doubtlessly expensive yacht berthed next to us. Good grief.

I gritted my teeth, gunned the engine, and Glamorous Galah reversed neatly out of her slip. Then I decided to reverse to starboard against both propwalk and wind. 

We cleared the end of the finger pier and were pointed in the right direction, yet we were being quickly blown toward the docks we just left. Teresa’s eyes were the size of dinner plates. I shoved the throttle into gear, and we surged forward. I faintly heard Anne-Marie’s amused voice call out, “You can slow down now!,” amid cheers and whistles erupting from the other boats.

Exhaling, I looked at Teresa for a long moment. It was graduation day. Our instructor was back at the Moorings dock, and it was just us and Glamorous for the next 24 hours.

It was hard to believe. Not only that I was skipper of my own 40-foot cruising yacht, but that I was doing it in March. In the Great Lakes offseason.

Offseason Charter School 

Many Great Lakes boaters look at winter as an inevitable hiatus, a several-month-long hiccup that brings on-the-water adventures to a halt for all but the most die-hard iceboaters and polar bears. 

It doesn’t need to be that way. Winter can be the perfect time to explore new cruising grounds, test different types of boats and even learn new lessons that you can bring back to your home waters just in time for the next summer season.

Consider this: When you charter a yacht in the lower latitudes, you instantly get a memorable vacation. You also have the opportunity to broaden your boating experience by cruising aboard a type of boat that’s new to you. This provides useful insights for possible future purchasing decisions, since a test drive simply can’t compare to live-aboard cruising.

And, best of all, many charter companies partner with powerboating and sailing schools to offer a variety of boater-education courses. Regardless of which you choose, you’ll be able to apply what you’ve learned to your Great Lakes boating life.

For my offseason adventure, I signed up for a week-long sailing charter with the Moorings, based on Tortola in the British Virgin Islands. The company joined forces with Steve and Doris Colgate’s Offshore Sailing School to offer a live-aboard cruising course just for women.

To qualify, we needed a US Sailing Keelboat Certification or equivalent sailing experience. I hadn’t had formal sailing lessons in years, so I would have to challenge the keelboat test if I wanted to continue to the next levels and earn my Basic Cruising and Bareboat Cruising certifications. This last designation was especially important, as it would allow me to charter a boat back home in the Great Lakes come summer. 

So, during the six-day, five-night course, I would work toward all three certifications through a combination of classwork, examinations and hands-on training. I was both eager and nervous—I had sailed small boats for a number of years, but at that time, my experience aboard large cruising yachts was limited. I didn’t know what to expect.

Our group was split in two: Four women on a Moorings 464 with instructor Michelle Boggs, and two of us on a new Moorings 403 with instructor Anne-Marie Belliveau. By noon on the first day, following a standard orientation in the Moorings briefing room, we were busy loading provisions and baggage onto the boats. Our 403, Glamorous Galah, seemed to have a particularly auspicious name for an all-girls sailing trip.

Teresa, my fellow student, a 30-year-old lawyer from San Francisco, busily checked all our provisions off the master list and stowed them in the icebox and cabinets. I double-checked all the necessary gear on board, from safety equipment to cooking utensils. After I checked each item off my list, I made sure I was well acquainted with its proper home.

As we motored out of Road Town Harbor into the Sir Francis Drake Channel, the easterly trades blew steadily at 10 to 15 knots. We hoisted the mainsail, bore off to the northeast and unfurled the jib. Keeping Tortola to port, we set a course for the tip of Beef Island.

Fortunately it was an easy afternoon sail, and it gave Teresa and I a chance to get a feel for Glamorous Galah. Our efforts were halting at first, requiring frequent assistance from Anne-Marie, but we were sailing. As our instructor, Anne-Marie’s job was not to sail the yacht; it was to make sure Teresa and I learned how to doublehand her ourselves.

A Nova Scotia native and lifelong sailor, 25-year-old Anne-Marie had a quick, bright smile and a rollicking sense of humor. She also had a calm, patient teaching style. There would be no yelling on Glamorous.

We rounded Beef Island and fell onto a broad reach, bound for Great Camanoe. As we neared the privately-owned island, Anne-Marie’s cheerful face clouded.

“I was hoping we could anchor in Cam Bay tonight,” she said, disappointed. “It’s through that gap between Great Cam and Scrub Island. But look, see how many boats are already out here?”

She pointed at a forest of bare masts at the Marina Cay anchorage, which illustrated the importance of arriving early in such a popular cruising destination.

“We could motor in there to see, just in case it’s not full,” she continued. “Or, we could drop the hook here and go snorkeling before the sun gets too low.”

Teresa and I looked at each other, grinning. We quickly dropped the sails and got ready for our first anchoring lesson. 

From Aragorn to Painkillers 

Our first class began Tuesday morning after breakfast—and after the unexpected challenge of brewing coffee with an old percolator (an experiment that was not altogether successful until later in the week). Teresa and I took our mugs into the cockpit, where Anne-Marie prepared to review the keelboat certification material and introduce several basic and bareboat cruising topics.

Just as the back of my neck began to bake in the intense morning sun, we heard an outboard motor approaching. Notebooks dropped and pens scattered as we scrambled to see who had pulled up alongside Glamorous. It was Aragorn, a legend from Trellis Bay (not Middle-earth).

Renowned as the largest arts and crafts center in the Eastern Caribbean, Aragorn’s Studio showcases prints, T-shirts, jewelry, copper sculptures, ceramics and countless other pieces of local artwork. Aragorn himself is Tortola born, and he frequently takes his boat out in the mornings, filled with merchandise, to visit yachts in the Trellis Bay and Marina Cay anchorages. 

Back to class. Now it was my turn to be captain while Teresa learned to operate the windlass. We stowed everything movable down below, closed all the hatches and portlights, ran the bilge pump, turned on the appropriate instrumentation, pulled in the dinghy painter and, when we fired up the diesel engine, checked all the gauges and listened for discharging water astern.

It was another close reach in a brisk east-northeasterly breeze to reach The Dogs, several uninhabited rocky islets that are diving and snorkeling favorites. We had lunch and snorkeled in the lee of George Dog, then continued to our night anchorage at Virgin Gorda. 

A skipper must pay close attention when entering Virgin Gorda’s North Sound, as this bay is surrounded by numerous islands and coral reefs. The Moorings asks bareboat charter skippers to use only the sound’s northern entrance, between Mosquito and Prickly Pear islands.

With a wary look at the breaking waves on the reefs, we left Mosquito well to starboard and the green channel buoy to port. As soon as Glamorous entered the embrace of Virgin Gorda’s broad arms, however, the sea flattened in the evening’s golden light. We hopped into the dinghy and roared ashore for a Pusser’s Painkiller at the storied Bitter End Yacht Club. Afterward, with our hamburgers sizzling on the cockpit grill and a cold Carib beer in hand, I worked my way through the keelboat exam’s 80 questions and earned a passing score. One down, two to go.

Passage to Anegada 

My travel alarm beeped insistently on Wednesday morning, but I smacked snooze and burrowed deeper into my blanket. With a pleasant breeze wafting through the open hatch and the soothing slap of water against the hull, I was easing back toward sleep. Then a bang and a clatter came from the galley. Anne-Marie was up.

Morning! I remembered in a rush that today we would sail 12 miles north to Anegada. Unlike its sister Virgins—all drowned volcanoes with rugged, mountainous topography—this coral and limestone island lies just 28 feet above sea level. It’s famous for its remote character as well for its infamous reputation; Anegada’s treacherous reefs have caused more than 300 shipwrecks. In fact, bareboat skippers aren’t allowed to sail there unless they’ve already been to the island with an experienced captain.

That was enough to get me out of my snug berth—that, and the promise of ever-improving percolated coffee. But Anegada would have to wait for a few hours. We had to go to school.

Since we needed practice pulling alongside a fuel dock, the first lesson dealt with docking and the back-and-fill procedure. Then we had our navigation and chartwork class, learning how to use a compass, dividers and parallel rulers to plot our position. This skill, supported by GPS, would be important today. Since Anegada cannot be seen until a yacht is nearly on top of its reefs, sailors can’t rely on piloting by eye as they would inshore.

Our docking and back-and-fill practice at the Leverick Bay fuel dock didn’t take long. Teresa and I took turns bringing Glamorous into the dock—one of us at the helm, one of us handling the lines, and the whole process making the dock attendants more than a little nervous. They didn’t look relieved when Anne-Marie explained that we were students.

As soon as we entered open water and set our course for the Setting Point anchorage on Anegada’s southwest coast, the supposedly reliable trade winds sputtered and faded to a gasp. We puttered along at 4 knots, then 3, then 2. I stared in disbelief at the knotmeter when it bottomed out at 1.5 knots. So we fired up the engine and motorsailed, agreeing that sunbathing and snorkeling at Loblolly Bay was worth far more than being purists.

It was a long, hot passage. Teresa perched against the railing all the way aft, studying US Sailing’s Basic Cruising book. It was my turn at the helm, and I kept myself busy dodging fish traps and trying to keep the fried backs of my knees out of the sun.

At last, an island-like mirage shimmered on the horizon, a thin line of blazing white and pale green. It was still early afternoon, which was a good thing. Our cruising guide advised that Anegada should only be approached in good weather and with the sun overhead, so you can see the bottom.

Loblolly Bay’s sugar-sand beach and teeming offshore reefs were, as we expected, an utter delight. Then we joined the other student crew at the Anegada Reef Hotel for its famous beach barbecue. With bare feet in the sand, fresh grilled lobster in half-shells on our plates and a twinkling city of anchor lights in the darkness, it seemed we were worlds away from everyday life. I didn’t think it could get better than this. 

I was wrong.

We weighed anchor at roughly 8 a.m. the next morning. Since the winds were still light and we had a long passage back to Tortola, we had our class and studied for the exams while under way. The wind gradually backed to the southeast and freshened. Even though we had to close reach yet again, at least we were sailing.

I was relaxing on the lee side of the cockpit, one hand on the helm, chatting with Anne-Marie. Suddenly her face froze, eyes fixed astern. She shrieked. In a panic, I whirled around just in time to see an enormous shape explode skyward. I have never been that close to a breaching humpback whale. 

Screaming and laughing, we fell off the wind, jibed and followed Anne-Marie’s instructions until we were properly hove-to. The whale didn’t disappoint us, arcing through the water, breaching once more and giving us a final, dramatic wave of his tail. 

We were left speechless, and we weren’t alone. A large charter catamaran caught up to us, and it was clear her crew had also seen the magnificent display. All we could do was wave happily at each other and shout, “Woo-hooooo!” It doesn’t get any better than that.

We ducked into the lee of Guana Cay to take the Basic Cruising exam, have lunch and leap into the crystalline water. Teresa and I both passed the exam, but even as we enjoyed the break afterward, the final exam still loomed on the horizon.

Graduation Day 

The last exam involved the yacht’s many onboard systems, from refrigeration to the diesel engine, as well as the vagaries of tide tables and currents. It proved easier than the second test for me, and both of us passed with flying colors. Now it was time to celebrate; we were officially graduates of US Sailing’s Live-Aboard Cruising course!

We visited the Last Resort in Trellis Bay after supper to see the hilarious “Singing Chef,” as it was Anne-Marie’s last night on board. The next morning we crossed the final item off our list, the crew-overboard drill, and slowly cruised back to Road Town to drop off Anne-Marie and take possession of our graduation present: Teresa and I would be co-skippers of Glamorous Galah for 24 hours, taking turns in the roles of captain and crew.

Traditionally, course graduates sail from Road Town to the Bight at Norman Island, a well-protected anchorage with plenty of available mooring balls. We picked up our mooring on the first try and eagerly dinghied off to sample the island’s highlights: Snorkeling the caves, which supposedly inspired Robert Louis Stevenson’s “Treasure Island,” and having a cocktail at the boisterous schooner-turned-watering hole William Thornton, affectionately known as the Willy T.

Aboard the Willy T, an older gentleman introduced himself, saying that he and several friends were on an annual guys-only charter cruise.

“Do you know what a stir you caused when you sailed in here this afternoon?” he asked. “Everyone was talking about it. No one could believe that you two were sailing that yacht on your own. Good for you!”

Later, after we’d gorged on steaks, baked potatoes and the Moorings’ best-kept secret, the chocolate mousse, we lay on the foredeck and talked.

“Isn’t that wild, that two women on a boat would get so much attention?” Teresa asked.

I thought about it. If two 30-something men were doublehanding a yacht, no one would think anything of it. Then again, I was really proud of us. Good for us, indeed!

Charter courses like this one are something special. Not only did I get an unparalleled learning experience, but I had the chance to bond with interesting women while cruising one of the world’s most beautiful places—and I got to stretch my sea legs while the water was hard back home. 

Not bad for the offseason.


While I chose to take a week-long sailing course through Steve and Doris Colgate’s Offshore Sailing School and the Moorings, you may prefer a boater education course aboard a powerboat. If you’d like to book an instructional power charter, the Colgates also offer their Power Cruise School — sister to the respected sailing school they founded in 1964. The Power Cruise School, in conjunction with the Moorings, has a fleet of NauticBlue power catamarans that it uses for its “Fast Track to Power Cruising” course. For more information, call 888-454-7015 or visit offshoresailing.com/power-cruise-school.aspx. – H.S.