two positions: Deck Hand - no experience needed
also: US Coast Guard Capt OUPV position available for our 2025 sailing season
Operating Mid-April until the end of Oct, 2025

Are You Passionate About Sailing and Customer Engagement? Join Our Crew!

Do you thrive on interacting with people and have a friendly, outgoing personality? We’re looking for enthusiastic Captains & Crew Members to join our vibrant sailing tour operation on the picturesque Chesapeake Bay in St. Michaels, MD.

About the Role:

Location: St. Michaels, MD
Vessel: A beautifully restored 1926 historic catboat, meticulously maintained for an unforgettable sailing experience.
Tour Capacity: Up to six passengers
Experience: Familiarity with gaff rigging is a plus but not required.

If you’re excited about sailing and eager to provide exceptional experiences for our guests, we want to hear from you!

How to Apply:

Send us a message with a brief introduction about yourself, why this position appeals to you, and what makes you a great fit for our team.

Come sail with us and be part of creating memorable adventures on the Chesapeake Bay!

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The boat is a 1926 historic yacht 44' long gaff rigged sloop, the largest surviving of any of the cat boats (not catamaran) built so she is roomy & stable. If you have a need for speed this is not your gig. If you like beautifully restored mahogany & polished bronze you are going to love this opportunity to sail the Miles river off the Chesapeake Bay. Pay is competitive.

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For the mate position No experience needed, just a love of the area and enjoy working with people. We are known for our customer service so a smile and friendly disposition is a must. The job is hard work but rewarding. Some of our crew have been with us 15 years. Position runs April to Oct but start and end dates are flexible,. Sun-Tues/Sun-Wednesday alternating weeks preferred schedule, but that is flexible too.