Chapter One: On Board

The lovely thing about cruising is that planning usually turns out to be of little use.
– Dom Degnon

A recent survey showed that happily married couples with kids had just one thing in common: Camping.

It had all to do with shared experiences, bonding, relying on each other in a pinch… Camping brings families closer, apparently.

I hate to camp. But I do like to sail. And “happily” and “married with kids” in the same sentence intrigued me.

So when my husband Dave officially kicked off his mid-life-crisis by announcing we were going to take our four children, ages 4-14, on a week-long sailing trip up the New England coast, I remembered that survey and brightened. After all, sailing is a lot like camping — just on the water.

That is, unless you own a yacht the size of a small mansion, which in case, you wouldn’t be bringing the kids anyway. You’d leave them behind with the nanny and bring along the cook.

We were renting a sailboat that was more like a small hut, and I was the nanny, the cook, and the first mate.  Dave was the Captain.

I was OK playing second fiddle as first mate. After all, navigating in calm weather appeals to me. But when the wind and waves start kicking up, chivalry appeals to me more. Storm approaching? No problem. “Captain Dave” was at the helm while mom stayed down under to make sure the kids were well-fed right until the end of their tender little lives.

Our trip was intended to be adventurous, but not overly ambitious. We’d be coastal cruising northeast along the New England coast, from Boston Harbor to York, Maine, and back. The ports we’d planned for overnight stays were some of the best: Gloucester, Massachusetts (think “Perfect Storm”); Newburyport, then Portsmouth, New Hampshire; and finally York, Maine. We also had a side trip planned to Isles of Shoals offshore from Portsmouth, a group of tiny islands in deep water formed from a great glacier.

Captain Dave had nearly three years of novice sailing under his belt. I had taken the beginner’s weekend course. So spending the night on the boat was a bit of a stretch. Navigating it hundreds of miles through uncharted waters for seven days? Delusional.

Of course, we didn’t see it that way back then.

“I’m not going,” declared our first-born son Jake when we proposed the idea. Jake hated to sail, and further had no intention of sharing cramped quarters with his three younger siblings for seven days.

We promised him we’d only sail a few hours each day, and then find a mooring and go ashore. We promised him he could wander around the towns on his own. We promised we’d buy him adult-size entrees at fine local restaurants. He didn’t bite.

I remembered when Jake was just seven and my husband and I had planned a ten-day getaway to Bermuda. We were dropping off the kids at a friend’s house to stay while we were gone. Jake didn’t want to go. We had to physically tear this tenacious kid’s fingers from the back doorway and forcefully muscle him into the minivan. As we were driving 30 mph down the road, he stood up, declared “I’m not going and you can’t make me!” and proceeded to open the side door of the minivan to jump out.

So this type of resistance from our eldest was nothing new. The only difference now was if he actually jumped, instead of roadkill, he’d be shark bait. And my husband and I, although both trained to perform the figure eight “man overboard” sailing maneuver, weren’t quite ready to have the first real man overboard be our son.

He’d probably swim away from us anyway. We’d never practiced that tactic.

We finally convinced him to go by pulling the perfect psychological ploy.

“OK, Jake. It’s fine if you don’t want to go,” I said coolly. “But you’re too young to stay by yourself. So I’ve talked to Miss Tanya, and she’s willing to stay with you for the week.”

We handed an almost 15-year-old the opportunity to stay home with a “babysitter.” He caved in.

“I guess I’ll go,” he sighed.

My other three kids were gung-ho from the beginning. Of course, my youngest, Caleb, at four, had no idea what we were getting into. He had no concept of the potential dangers of unpredictable weather, malfunctioning equipment, and avoidable mistakes every greenhorn sailor makes that can spiral into near-disasters.

Neither did I.

In the weeks before our trip, Dave plotted our course while I plotted our provisions. The boat we were renting was a 20-year-old, 40-foot Cal ocean cruiser. Don’t let the 40-foot part delude you. The cabin of the boat theoretically slept six, assuming an adult height of no more than five feet, and assuming two people would sleep comfortably on the 18-inch wide galley cushions. Neither was true for our family.

Packing six people for a week-long sail on a 40-foot boat doesn’t sound difficult, until you are actually packing. There were life preservers, first aid equipment, sheets, towels, blankets, pillows, and clothes — times six. Then the food: Three meals per day times 7 days times 6 people. That’s 126 meals. And that doesn’t count snacks, which is all my kids truly care about anyway.

And of course, Jake HAD to bring his guitar. And Chloe, my 12-year-old daughter HAD to bring all of her music. And then we HAD to have games. And I HAD to have my special pillow, the only one I can sleep on.

I became the guard dog of gear.

“No, you are NOT bringing your laptop.” “You don’t need a sweatshirt and a sweater and a jacket. And forget the make-up bag.” “Sorry, Caleb, you’ll have to use your sweatshirt for a pillow. There’s no room. I know Mommy has a pillow, but that’s different. Mommy has allergies.”

After a week of tense negotiations, stand-offs, packing and repacking, we finally were on our way. We hired a retired limo driver, Don, to take us down to Boston in his Chrysler minivan.

It was a cold, wet day in August. In fact it was pouring buckets. We quickly stuffed all our things in the van, then squeezed ourselves around it all. I’m still not sure how we managed to get the doors shut.

“So, you guys sail a lot?” Don, our driver asked, trying to make conversation in the congested inbound traffic.

“Yes,” Captain Dave said.

“Not really,” I said at the same moment.

“I see,” said Don. “You know, I’ve never sailed before, but my wife and I love to camp.”

“Really?” I replied. Bet they have a happy marriage, too. Survey says!

“Yes, we take the summers off and go across country in our motor home. We’ve had some terrific trips.”

“Sailing is a lot like camping,” I offered. “Adventuring new places, on the go, staying in a different port every night…”

“Never thought of it that way,” said Don. “Where are you guys headed on the sailboat?”

“Oh, we’ll go to Gloucester, then up to Newburyport and Portsmouth,” answered my husband. “We’re hoping to get to Maine.  That’s our goal.”

“Where will you go the next day?” asked Don.

“That’s the whole week,” said Captain Dave testily. I sighed. “We’re planning about 25 miles a day, which is a lot when you’re sailing.”

“Really? Well sounds like fun…” Don put on an enthusiastic voice. Outside the rain kept pouring down.

“What do you do in bad weather like this?” he asked.

“You motor,” said Captain Dave.

“Is that any faster?” asked Don.

“Not really,” said Dave.

“I see,” said Don.

I’m sure Don thought we must be idiots to spend an entire week getting somewhere by boat that he could cover in an afternoon in his spiffy motor home.

We finally arrived at Boston Harbor. Don opened the doors, and our stuff tumbled onto the street. We quickly worked to lug kids and duffle bags and pillows and blankets down to the dock in shifts, trying to avoid eye contact with the tourists. We looked like homeless kleptomaniacs.

At the dock we radioed the Boston Sailing Club launch to take us to the boat. “Small Hotel” the name wittingly given to the vessel, was to become our home for the next seven days and nights. The launch driver, Mark, helped us load our stuff into the launch.

“Where you going?” he asked.

“Maine,” I said. It sounded better this time than with Don. This guy sailed. He knew.

“Sounds great.  S’posed to clear up soon,” he offered, looking at our sorry wet crew in their rain gear.

Mark took us to the boat. It took an hour to unpack everything enough to even move around the cabin. Dave checked the gas, the GPS, the propane and stored the 10-pound sack of charcoal we had brought along for outboard grilling. Bad weather had never been part of the plan.

Somehow, amazingly, the rain ended just as we were ready to go, and a nice breeze began to blow. We attached the main halyard securely, or so we thought. I let off the buoy line and we were underway.

Had I known then what adventures the week would hold, I would have probably asked for my money back, taken my pillow and jumped ship.