Sponsored by Offshore Sailing School

Sail to Suit Your Goals

Learn to become a confident bareboat skipper, overnight aboard, and explore foreign cruising grounds with ease.

January 12, 2016
Offshore Sailing School

With the basics in your wake, now you want to know and do more. Here’s advice on learning how to become a confident skipper on a bareboat charter; overnight aboard a boat; and explore foreign cruising grounds with ease.

You’ve gotten your sea legs. You’ve done some afternoon and sunset cruises on your boat or a friend’s. A few Wednesday nights you joined a yacht club crew for some beer-can racing.

Now it’s time to try something different. You want to handle all the aspects of a bigger boat, including living aboard. You want to charter a monohull or a catamaran or a power boat on your own, either in the Caribbean or the Mediterranean. You want to feel confident at the helm and you want the freedom that self-sufficiency aboard lends. Or you want your partner to share in the joy — and the hands-on-tasks. Or maybe you want to “put the zing back” in the time you spend together as a family.


Through a combination of how-to manuals, classroom time, and on-the-water lessons, as well as vacation/onboard packages, schools offer a range of intermediary courses for aspiring skippers and crew. Some offer tiered curriculums, while others offer custom instruction. Some courses are offered in sought-after destinations, while others are available closer to home, whether on a coast, a lake or river.

“People want a fully immersive experience and they want to do it under the guidance and security of an instructor,” says Kevin Wensley, director of operations for Offshore Sailing School. “What a good school will do is show them how to plan and prepare and understand the safety procedures.”

At this level, whether the course is described as learn to cruise, charter, or live aboard, the focus will include navigation and rules of the road, understanding weather forecasts, anchoring, docking, safety, and overnighting aboard. “Get experience in those and there’s not much stopping you from sailing anywhere in the world,” Wensley says.


That was the goal for Lisa Gabrielson, an experienced inshore and ocean racer who completed the weeklong Fast Track to Cruising with Offshore in the British Virgin Islands. “Even though I’ve raced a lot, I’m crew, not the skipper,” she says. “To have those two days to get confident on the helm on the Colgate 26 with the instructor, when I went to the 52-footer I was much more comfortable. Docking was another major skill I wanted to work on. I hadn’t done it in a boat bigger than a J24. I now feel like I can go to the Caribbean and do it tomorrow. I’m even interested in gaining multi-hull certification.”

For Steven Gray and his wife, parents of two teenage girls, sailing is a metaphor for strengthening family bonds. In 2014 the Grays completed an introductory five-day Learn to Sail course at Offshore’s Pink Shell Resort in Fort Myers, Florida. Their powerpoint presentation of the experience won them a Liveaboard Cruising course with Offshore a year later — which was fortuitous, as they’d just bought a boat to keep in the waterways near their home in the Norfolk Broads region of the United Kingdom.

“Gaining a sense of achievement with something that had seemed out of reach — and seeing the look of sheer pride when the girls plotted a course while under sail and we reached the right marker in the right place at the predicted time — were priceless!” he says. “We worked hard to complete the course, had fun along the way and now all have our International Proficiency Certificates.”


The IPC, (the ICC, International Certificate for Operators of Pleasure Craft, is administered by the Royal Yachting Association), is the ticket to exploring the Mediterranean on charter. It’s mandatory for vacation sailors throughout the region, though the requirement may vary country by country. Both the American Sailing Association and U.S. Sailing, the governing body of the sport, issue the certificate to qualified candidates who’ve successfully completed introductory through intermediate level courses.

“When people prepare properly and gain confidence, it truly changes the way they look at sailing, whether their goals are the Florida Keys or Croatia,” Wensley says.

For more information about liveaboard courses, including the Fast Track to Cruising, Liveaboard, and the IPC, click here.


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