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There's a First Time For...Buddy Cruising

A new sailing friend asked me recently, “Do you ever buddy boat?” “Not really,” I started to say, but then changed my answer to, “Sure, often.” She could see the confusion her simple question had created and laughed. “Betsy, is everything about sailing and cruising always so complicated?” Let this article be my answer to my friend and to others who wonder the same.

A new sailing friend asked me recently, “Do you ever buddy boat?”

“Not really,” I started to say, but then changed my answer to, “Sure, often.”

She could see the confusion her simple question had created and laughed. “Betsy, is everything about sailing and cruising always so complicated?”

Let this article be my answer to my friend and to others who wonder the same.

First, let’s divide “buddy boating” into two categories: BB1 and BB2.

BB1 includes those glorious times when friends on another boat say something like, “What are you doing over Fourth of July Weekend? Want to take our two boats over to Provincetown?” Both crews make plans to leave their home harbor at a certain time and to stay in sight while crossing Massachusetts Bay. Once in Provincetown, they agree to have the first dinner on one boat and the second on the other. In the meantime, they stroll the town, visit the galleries and take a bus to the dunes. Three days later they sail home, once again staying within sight of each other, their friendship likely twice as strong as it was before.

BB2, on the other hand, is when friends, or more likely acquaintances, say, “We heard you’re going straight through from Boston to New York City, taking the ocean route outside Long Island. We’ve never sailed at night. Can we tag along?”

This is when your uh-oh flag should start waving. BB2 usually means that the less-experienced boatwants a bit of babysitting. On our Gulfstar 39, Salsa, my husband, Monty, and I were once newbie cruisers like this, relying on someone else to take us in hand and help us down the U.S. East Coast or along foreign shores and up strange rivers. We’ve also been the experienced boat, helping others across the Gulf Stream or the Bay of Fundy to Grand Manan. Sometimes this has benefited us as much as it has our inexperienced partners, providing us with a new set of lifelong friends—but not always.

An example: Ken and Leigh had never been offshore, but while they were nervous, they were also well prepared. We agreed to cross the Gulf Stream with them and to stay together at least until Nassau. At the last minute, another couple we didn’t know asked if they could join us with their catamaran. We couldn’t say no, but we should have. 

The Gulf Stream crossing was smooth, but the Bahamas Banks were a challenge. Ken and Leigh got to Nassau with us, a bit white-knuckled, but proud of their achievement. The catamaran, though, was not seaworthy, and neither were its owners. They didn’t even have a radio. They blew out their jib and limped into Nassau, where they had to borrow money for repairs. We’re still close friends with Ken and Leigh. The others? Not so much.

If you still want to try BB2—either as the experienced party or as the beginner looking for companionship—I recommend asking the following: do all the boats traveling together sail and motor at approximately the same speed? Are they and their crews in good shape and well prepared? What are everybody’s expectations? If one boat has an equipment failure or experiences an accident, what should the other boats do? What about radio contact? Do you want to be joined at the hip? Or do you just want a buddy boat for sundowners in the next harbor? BB2 can be a wonderful informal system, and it works most of the time. But if it doesn’t feel right, don’t do it. Another buddy will come along.

Back to BB1: No such warnings apply. We’ve sailed with our friends Jenny and Rod on their Cape Dory 33 Ragtime in and out of the great bays of Maine on a number of occasions. We’ve hiked together, gathered wildflowers together and shared meals. One time, when we felt like an extra day in Castine, they sailed on and we met them a few days later in Blue Hill. We’ve worked on a clogged head together (well, that’s not entirely true: Monty and Rod worked on the problem while Jenny and I played Scrabble), I’ve helped Jenny with a sail repair, and the four of us once spent a hilarious afternoon painting their dinghy on a remote rocky beach. 

We’ve also enjoyed longer passages, sailing in company with friends down to the Leewards and the Windwards. How many times have we retold the story of Monty falling overboard just as all three boats were screaming at hull speed toward the mooring balls below the Pitons at St. Lucia? I’ll also never forget the time we anchored with friends in the Shark River on the west coast of Florida, and we all saw a group of alligators not 30 feet from where we were having drinks in our cockpit.

One day I did a stupid thing. I was reading when I was supposed to be paying attention on watch and I banged right into a huge marker on the Intracoastal Waterway, tearing our jib. Later, when we were safely anchored in St. Augustine harbor, my friend Beth from Anasazi dinghied over to help me haul the jib around onto the cabintop where I’d set up my sewing machine to repair the damage. Buddy boating friends are the best! 

Then, of course, there have been countless shorter trips with friends: a picnic in Manchester harbor; another in Gloucester; an overnight at Swan’s Island with Meltemi for the Sweet Chariot Music Festival; a lee-rail-under sail with Mary Constance from Buck’s Harbor to Stonington for the Flash in the Pans Concert; a couple of nights in the Boston Harbor Islands; a couple of more in New Hampshire’s Isles of Shoals.

Many of the memories we hold dearest are the ones we share with others, making buddy boating more than worth the risk.

Photo by Tor Johnson

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