Key West, FL
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Our Crew

Classic Harbor Line Key West Crew is the operating the Schooner America 2.0 out of the Key West Bight. Operating sunset sails and day sails on Key West waters since 2008, Classic Harbor Line specializes in bringing beautiful, classic-style yacht to the Key West waterways and creating special and memorable excursions. 

Our Crew, including all captains, mates, chefs, and on-land representatives at Classic Harbor Line, is what make the experience on our beautiful yacht truly magical. We have maintained a consistent history of not only operating with a professional staff, but also with warm and inviting hosts. You will, without a doubt, get a fantastic glimpse of the green flash on your Key West Sunset Cruise and find this yacht beautiful and comfortable, but what will surprise you and stay with you when you leave is the warm and special treatment you receive from our extraordinary team.

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.

Our Mates

Mates on the Schooner America 2.0 undergo extensive safety and marine training. Many of the schooner mates also have extensive sailing, racing and/or teaching experience on smaller sail vessels.

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 great island of Key West, and conveying their love for our classic-style yachts and the addictive mystique of being out on the water. If you are interested in joining our crew, please send a cover letter and resume to: [email protected]

Our Land Ambassadors

There are a number of behind-the-scenes crew members at Classic Harbor Line Key West. They are the team who answers the phones, plans your event, greets you on the pier and is happy to tell everyone about the cool cruises and sails that we offer.

Everyone who buys a ticket for trips gets to meet a Land Ambassador at check-in. They are full of information and they are the most hospitable people you will ever meet! Ask them for recommendations on dinner after or before a sail or a suggestion on a future excursion.

Employment with Classic Harbor Line

If you are interested in employment with Classic Harbor Line Key West, we want to hear from you! We are always looking for experienced captains and mates with a strong background in hospitality and/or marine maintenance. Please feel free to forward a letter and resume to [email protected].

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