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Our Crew

Classic harbor Line Key West - Our Crew

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

Our Key West Crew, including all captains, mates, chefs, and on-land representatives at Classic Harbor Line Key West, is what makes an experience aboard our beautiful Schooner America 2.0 truly magical. We have maintained a consistent history of not only operating with a professional staff, but also as warm and inviting hosts. Guests aboard Schooner America 2.0 may experience a glimpse of the green flash on a Key West Sunset Cruise  or enjoy a day of sightseeing in Key West on a sightseeing boat ride. Our Schooner America 2.0 team hopes that you’re able to create lasting memories that will stay with you when you leave due to the warm and special treatment you receive from our extraordinary Key West team.

Our Captains
All of our Key West captains are Coast Guard certified. The Schooner America 2.0 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

The Key West 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 sailing yachts.

Our Key West 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 by filling out our employment form.

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 private yacht charter events, 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 Classic Harbor Line Key West 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 Key West sailing 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 fill out our online application and attach a cover letter and resume.