All the sailors who participated in the World Cruising Club’s (WCC) 2014 DelMarVa Rally this past June had one goal in common: start small, build big. At least that’s what Mark Johnson, skipper of Aisling, told me at the prize-giving ceremony afterward.

Unlike those sailing rallies that span oceans or circle the globe, the DelMarVa Rally covers just 450 inshore and coastal miles around the DelMarVa (short for Delaware-Maryland-Virginia) Peninsula—starting in Annapolis, Mayland, and then heading down the Chesapeake Bay to Portsmouth, Virginia, up to Cape May, New Jersey, and back to Annapolis through the C&D Canal.

However, while the seven-day trip may be more manageable than a rough Gulf Stream crossing, ask any of the crews that sailed in the 2014 rally, and they will tell you it was anything but “small.” With 20-knot headwinds pretty much every step of the way, 48 hours of fog and three major storm cells to cope with, these sailors, some of who were on their first rally, had a learning experience they’ll be able to talk about for years to come.

A TOUGH START

On arriving at J/World Performance Sailing School in Annapolis on a Saturday, I met Robin Wells, an energetic woman with whom I would sail the first two legs of the trip. She and her husband, Gary, had moved aboard the Amel Super, Adagio (named for their shared passion for music), the day before (so much for starting small). They had dreamed of living aboard for years and joined the DelMarVa Rally to shake down Adagio, hone their skills, spend time with their friend and crewmember, Erle, and make some new friends.

Together we made our way to the skipper’s meeting, where rally leaders Andy Schell and Mia Karlsson gave a briefing that included tips and tricks for the week ahead. Andy’s encouragement and the information he shared helped ease everyone’s concerns, and there was plenty of lighthearted banter. “Be as competitive as you’d like at the start, but know that all over-early boats will be publically humiliated,” said Andy, eliciting a chuckle from the crowd. With that, it was back to Adagio to rest up.

At 1000 the next morning, we hoisted our DelMarVa flag and set off with 22 other boats for an overnight sail south to Portsmouth, Virginia. Soon after the start, gray clouds rolled in and the wind kicked up to 20 knots out of the south and on the nose. We fought Chesapeake chop the entire way and after a grueling first day dropped sails at 2200 and started motoring. Erle and I took the first watch, battling seasickness throughout the night. The fleet struggled, and a few boats even had to turn back due to electrical failures or queasy crew.

Fortunately, while the weather never improved for long, the following morning we sighted another rally boat, Mystic Shadow, in the distance and hailed them often to check in and raise spirits. In fact, communicating with other sailors like this was easy, because Andy had set up a series of daily radio nets that included weather reports and position recording for each boat.

Ultimately, we sailed for over 36 hours on that first leg, and we eventually reached Portsmouth at the mouth of the Chesapeake and picked our way through the shipping channels there to the Ocean Marine Yacht Center, where we tied up at 1700 on Monday. As soon as we did so, we celebrated with Coronas and then set out in search of dinner, eventually finding a place downtown where we feasted on a local favorite dish of chicken and waffles coated in cinnamon apples. Over dinner, Robin told me how thrilled she was to be part of the rally. “I’m learning so much. I’ve gone from asking what button to press and saying, ‘Whoops, not that one!’ to navigating my way down the Chesapeake. It’s pretty neat.”

Other boats continued to trickle in throughout the night and following day. Then on Tuesday evening, we all joined together for a happy hour and dinner. Despite the day-long delay in our schedule, everyone was in good spirits and after a night’s rest we were all ready to tackle the rest of the trip.

GOING THE DISTANCE

For the next leg of the journey, I jumped on board Remedy, an Island Packet 420 out of Rock Hall, Maryland. Though owners Janette and Lee Davis had spent many seasons gunkholing in the Chesapeake, they were ready for something new and had joined the DelMarVa to experience a WCC-run event. Lee’s brother, Ed, joined them as crew.

Together we rose with the sun on Wednesday and set sail for the Atlantic. The start was calm, and with dolphins swimming to starboard, we hoped to make Cape May the next evening. Our hopes were dashed when a thick fog settled in, and the wind started blowing, this time 20 knots out of the north so that it was once again on the nose. Next thing we knew, Remedy was fighting four-foot ocean swells in the rain, with the foghorn blowing and everyone on watch, as we motorsailed at a steady 7 knots for over 24 hours.

Still, while the conditions may have been tough, they also provided a great learning experience for those more accustomed to inshore sailing. As Ed put it: “We wouldn’t typically have gone out in these conditions, but now, with the rally, we can see what everyone else is doing and learn what to do and what not to do.” Janette also became more comfortable, Ed said. “One day, she came up on board, put her hands on her hips, looked at the chartplotter and said, ‘Hey, I don’t think we’re making much progress. Let’s turn on the motor.’ She made the decision for herself.”

That night, in the hopes of making more ground, we agreed to skip Cape May and sail straight up Delaware Bay. Boats with masts 55 feet and taller, like Remedy, had to sail offshore the “long way,” instead of transiting the Cape May Canal, so we radioed our plans to the fleet, and some followed suit.

Wrapped in blankets and foul-weather gear with hot tea in hand, we pressed on through the night. At 1500 on Wednesday, we arrived at Delaware City Marina and awarded ourselves with a meal at the renowned Crabby Dick’s restaurant. By 2200, we were passed out in our berths.

YET MORE WEATHER

Things looked brighter Thursday morning, as we took off in a light breeze under sunny skies toward the C&D Canal. That afternoon, with the current running against us, we motored through the canal, jazz music blaring, as Janette and I snapped photos of blue herons from our perch on the bow and Lee acted as our tour guide, chatting about random trivia through Remedy’s loudspeakers.

Around noon we dropped the hook for lunch and explored Chesapeake City, a hotspot on the canal. It was then that I learned how crucial it is to communicate effectively via VHF and to continually check the radar, when we started hearing flash flood and thunderstorm warnings as we were preparing to head out again. We radioed Andy to alert him of the impending storm, and thanks to the rally grapevine, most boats were able to find a safe spot or dodge the weather. Mid-afternoon, Zephyr and Tres Hijas pulled into the anchorage with us and together we found ways to pass the time.

After the thunderstorms had passed, we continued through the canal. Thanks to our overnight stop, we weren’t too weary, and I was grateful to have Lee as skipper, especially because he had such great local knowledge. He pointed out, for instance, that the merging currents of the Sassafras, Northeast and Elk Rivers make the Chesapeake a bear to sail. He knew, too, that once we reached Turkey Point there would be little traffic, and we would be golden for our final run to Annapolis. Lee never hesitated to share his knowledge of the area or his passion for sailing with anyone who would listen, which kept his crew engaged despite the gnarly weather.

We arrived in Rock Hall, Maryland, that night after being chased by yet another lightning storm. Once again, Lee’s knowledge came in handy as we tried to spot navigation aids in the pitch black. We arrived earlier than the rest of the fleet, so we spent the following day resting and working on Remedy. After that we drove to Annapolis on Saturday for the awards ceremony. Again the mood was lighthearted and encouraging as Andy and Mia handed out several awards such as “Best Logbook,” which went to Robin and Gary, “Best Bruise,” the “Hero Award,” and plenty more.

It quickly became apparent that the crews I had been a part of weren’t the only ones to confront some serious challenges and learn important lessons during the Rally.

Mark Schaefer, skipper of Dana Marie, for example, told me how his power cut out three-quarters of the way into the first leg at 0200. The crew of Wine Dog came to his rescue with a spare Honda generator that allowed Dana Marie to arrive safely in Portsmouth. “Everyone has been so generous. It was a struggle to keep up with the rally schedule given the weather conditions, but it was wonderful to sail with other people. At least we’re in it together,” Mark said.

Another sailor who had clearly grown from the passage was Tim Foster, skipper of Molly Kate, a Beneteau 321, who had joined the DelMarVa to gain experience beyond his typical weekend sailing. His crew of four had been put in charge of the radio net the first day. Said Tim: “It was the adventure we thought it would be. During the radio net we relayed the weather report and then cracked bad jokes. Little did we know our VHF wasn’t connected at the top of the mast, so no one heard! When we didn’t hear anyone laugh, I thought, ‘I know our jokes are bad, but I didn’t think they were that bad.’”

Though some who sailed together were already friends, others began the rally as strangers. On board Aisling, skipper Mark brought his crew together through a post on meetup.com. Alan Boroshak responded to the post, and though he had already been sailing for eight years, he was totally bitten by the rally bug. “Sailing in a rally forces you to acclimate quickly. I love the social aspect and playful competition,” he said. “This is something anyone can enjoy. You just gotta do it.”

As the evening came up to an end, Andy took the stage and wished everyone great future sailing adventures. “Everyone learned something this trip,” he said. “Rallying is about getting through things together. It’s the people you meet that make it an adventure, and I can’t wait to see DelMarVa flags hoisted on boats around various ports in the world.”

Neither, I’m sure, can many of the sailors themselves.