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Posted by on May 1, 2013 in Boating Lifestyle, Sailboat, Sailing, US |

Living the Sailing Dream, Part Five

Next stop: Finding valuable experience on a boat.

This is the final installment of the Living the Sailing Dream series. Read: part one | part two | part three | part four

For Leah, the dream was just beginning.

While Erika and I scrapped our plans to buy a 40-foot sailboat after realizing how much we didn’t know about boats, we did have a plan B.

Our goal was to get experience. We were already experienced divemasters, but we knew it would be hard to find a job on a boat unless we were certified instructors. So off to dive instructor school we went, completing a fast and furious course of a few weeks. During that time Erika got a recommendation for a position on a liveaboard dive fleet called Blackbeard’s Cruises.

These were 65-foot sloops that housed six crewmembers and 24 passengers as they crossed the Gulfsteam each week, headed for the Bahamas. Tight quarters to say the least, as rooms were separated by curtains with only two heads on the boat for all those people. Talk about camping at sea.

Erika was thrown into the fire as a dive instructor/deckhand doing dinghy maintenance and compressor maintenance.

I, on the other hand, attended a dive show in Ft. Lauderdale and met a well-connected guy who knew the owners of the Aggressor Fleet. This premier liveaboard diving company has boats all over the world. I was salivating. This could be a really cool job! I managed to impress him, and by the end of the show he introduced me to the big man himself — the owner.

I don’t know what I did to impress him or how my meager resume got me a tryout on the Cayman Aggressor. This 110-foot, 200-ton luxury liveaboard had no resemblance to a sailboat whatsoever, but it was on the water, it was diving in the tropics, and it was an amazing opportunity.

It all happened so fast. I got a round-trip ticket to the Caymans and worked for a week for free. Then I got a one-year work visa to become part of the six-person crew, serving up to 24 passengers for up to five dives a day in the pristine waters of the Caymans. Not a bad gig.

Everything came together, and I spent the next year learning about boats in the Caribbean while diving on colorful reefs in crystal clear water. I later got a captain’s license and sailed on amazing sailboats from 50-foot monhulls in the BVI’s to historic replicas of topsail schooners down the east coast of the United States. My sailing took me to Africa and through almost every island from Bermuda to Grenada — as I lived the sailing dream.