The O Words - Offshore, Ocean, Overnight

Many years ago a cruising lady we met in the Bahamas told me there were three words she didn't want to hear from her skipper. She said these were the O-Words - Ocean, Offshore and Overnight. The O-Words meant she had something to worry about in the upcoming voyage.

Hmmm, did my mate worry about such things? As a young cruising skipper I knew you have to keep the crew safe AND happy!

Sailing Azores800
Our Classic 37, “Two-Step”, in the Azores following our third transatlantic passage.
(The voyages of Two-Step in Distant Shores seasons 1-4)

Sheryl and I were on our first international cruise when we met this lady. We'd travelled down the Intracoastal Waterway, then jumped across the Gulf Stream to the Bahamas to discover crystal blue waters, fine white sand and warm breezes. All our compatriot cruisers had sailed many miles also, mostly more than 1,500 miles, to get to this point. This cruising lady had experience but had been traumatized somewhere on that trip south. Sheryl and I were sailing on our 37-footer "Two-Step" and had been enjoying the trip taking things slowly and step-by-step building our confidence and experience. There was lots to learn but we knew it and had lots of fun. So how had we avoided being traumatized by the "O" Words?

Starting Out

Rewind 6 months… we had just begun our cruising adventures aboard our homebuilt Classic 37 sailboat and were very conscious of our lack of experience. We had both grown up with boats but powerboats, not sailboats, and following a dream of making a long-distance voyage to the tropics we had learned to sail in Georgian Bay four years prior, then had sailed a number of miles in Lake Ontario. We had even chartered in the British Virgin Islands (BVI) but we had never sailed Overnight at that point. We had sailed in the Ocean there but had not sailed Offshore. So we had only bagged one of the O-Words and since it was just sailing around the BVI perhaps it didn't even count as real Ocean sailing.

Completing our fifth transatlantic crossing aboard our Southerly 49, Distant Shores II
(Canary Islands to St. Lucia with the Atlantic Rally for Cruisers, Distant Shores season 9)

Mastering our first proper O-word came as we set sail from Toronto, Canada, in September 1989. We did our first Overnight across Lake Ontario, an inland sea with a lot of large Great Lakes ship traffic, to Oswego, New York, where we cleared into the USA and entered the New York State Canal system that led us to the Hudson River and New York City. From New York Harbour we headed out into the Ocean which we were pretty nervous about. So we didn't push. Although other more experienced sailors headed out before us we waited for really good weather and, getting up really early, sailed gently south down the coast in the Ocean in daylight hours to Atlantic City. We didn't want to combine Ocean with Overnight the first time out nor scare ourselves by trying it in rough weather. We promised one another if one of us wasn’t happy we would go back. Honouring that allowed us both to stretch ourselves a little knowing that we could count on the other to turn back if one of us was uncomfortable.

We did one more day of the Ocean sailing to Cape May, then next came the Chesapeake Bay, a wonderful cruising ground full of bays, rivers, and creeks for anchoring plus delightful towns for exploring. After making a few improvements to the boat at the numerous well-stocked chandleries there we headed down the Intracoastal Waterway in the fall of 1989. Massive Hurricane Hugo roared through in September and amongst other damages forced the closure of a bridge, and hence the stretch of ICW from Georgetown to Charleston, South Carolina, was blocked. We had been enjoying the delights of the ICW route south until this point and hadn't been in the Ocean since our quick hops from New York to Atlantic City and Cape May a month earlier.

First Overnight

I looked at the chart and with calm weather conditions in the forecast I saw the opportunity to plan our first Offshore Overnight passage. We would head out to the deepwater sea-buoys offshore and sail down the coast. Winds were forecast to be light and the seas were relatively calm. We weighed anchor around midnight and slid down the river with the tide heading offshore from Georgetown to arrive in Charleston SC in daylight. Stars twinkled overhead and smooth seas were a gentle introduction to our first Offshore Overnight sail. We both stayed up as we headed Offshore. We hadn't planned a real watch schedule for the first part of the night since it was just a few hours down the coast and I think we were both excited. We both stayed up until we picked up the outer sea buoy and then took turns napping. Now we always establish a proper watch schedule.

I think I was somewhat lucky that our first Offshore Overnight was so nice. It was a bit rougher as we beat the remaining 8 miles back inshore to the channel mouth on the approach to Charleston. But we had done it! We did our first Offshore Overnight on the Ocean and it had been the furthest Offshore we’d been up to that point. The first mate was happy and we celebrated with a dinner out in lovely Charleston. "Keep it fun for everyone!”. We both agreed that the tradition of a celebratory dinner out as a reward would make the tougher passages we might face in the future more bearable.

SB At night800
Sheryl on night watch sailing north through the Bahamas
(Distant Shores season 10)

If you are planning for your first "Offshore, Ocean, and/or Overnight” it makes sense to plan a trip that gives everyone a chance to appreciate the wonders of a nice experience. There will be time to tackle tougher conditions and rougher passage-making down the line but once your crew knows how nice it can be they will be ready to build on their experience in easier stages. The beauty of the open ocean can be worth a little discomfort, and the sense of accomplishment will help build the crew into a team.


Meeting more than one traumatized crewmember from other boats on that first trip south really had an effect on Sheryl and me. We could see how easy it could have been to avoid the conflicts and fears some of our fellow cruisers were experiencing by making simple changes in pace and/or attitude. From then on it became a mission to help people achieve safe, comfortable and harmonious voyages with their friends or loved ones through our writing and television programs.

On September 21st, Sheryl and I will be celebrating 25 years of international cruising together as well as the production of our 125th episode of the Distant Shores sailing TV series which features the world’s best sailing destinations and the launch of our new how-to series, “Let’s Go Cruising!”. The first DVD/download of “Let’s Go Cruising” will be about Anchoring using footage we’ve shot in many exotic locations around the world in all conditions. We invite you to subscribe to our newsletter to receive updates on this new series plus tips and advice as well as a free download of “Southern Exumas, Bahamas”, a half-hour episode from season 5 of the Distant Shores sailing TV series as a bonus gift.

Please share your experience. How did you deal with your first Overnight sail or prepare your crew for theirs?

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