Key West, FL
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Thinking about Employment with Classic Harbor Line?
Learn more about our crew
Our Captains

Our Captains

All of our captains are Coast Guard certified. The Schooner captains all have a minimum 100-ton license and a sailing endorsement. Our captains are also trained in first aid and CPR and are registered in an ongoing drug-testing program. Perhaps of equal importance, we require that our captains have an appreciation for quality service and are extremely charming hosts. Many of our captains started at Classic Harbor Line as a deck mate. If you are hoping to be a captain, a great way to start is to learn to be a deck mate.

Our Mates

First Mate, Second Mate & Third Mate

Maybe you have sailed several schooners before or maybe you grew up sailing or with a family boat. Chances are, if you are interested in a marine crew position, you will likely start out as a trainee, then a third mate or second mate once you have ‘gotten the routine’ and you have passed your pre-employment drug test. Our mates are widely remembered for their remarkable hospitality and personality which is consistently praised in our customer reviews. They love talking with our guests, sharing information on the island of Key West, and conveying their love for our classic-style yachts and the addictive mystique of being out on the water.

Our Land Ambassadors

Land Ambassadors & Sales Representatives

Maybe you have hosting experience, front of house, or ticketing experience. If you enjoy talking to the public and taking care of guests as they arrive, then being a Land Ambassador may be the job for you. This part of our crew helps set the tone for the experience our guests are about to enjoy. They must be welcoming, cheerful and able to take care of check in logistics quickly. Basic computer experience and comfort with making phone calls is a must!

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