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  • SailSelina

    • 42ft 42' ketch
    • United States
    • Checked in 1 week ago

Deckhand - Temporary / Seasonal - Min exp 0 years - $base stipend plus split tips - United States

Join Sail Selina's Crew:

Historic Sailboat Position in St. Michaels, MD

Do you love interacting with people, exploring the beauty of the Chesapeake Bay, and being part of a dedicated, fun team? We’re looking for a friendly and reliable individual to join our crew aboard the historic 1926 Selina II, a classic gaff-rigged catboat. Based in the charming town of St. Michaels, MD, this is an exciting opportunity to help create unforgettable experiences for our guests.
The Role:

As a Crew Member, your main priorities will be reliability, willingness to learn, and excellent communication skills. You don’t need years of experience—just a passion for all things sailing, a positive attitude, and a love for serving customers!

Here’s what you’ll be doing:

Morning Prep: Cleaning, sanitizing, and setting up the boat for the day (cleaning, cleaning, and more cleaning!).

Guest Interaction: Helping guests board, handling lines, and providing a warm, welcoming experience. You’ll engage guests with interesting stories about the history of the Selina II, the Chesapeake Bay, and its ecological and conservation efforts.

Sailing Operations: Assisting with the heavy sails, handling the mainsheet, and occasionally steering the boat. You’ll get the chance to learn the ins and outs of operating a historic vessel!

Guest Services: Serving refreshments, entertaining guests, and ensuring a memorable sail.

Evening Clean-Up: After the final sail of the day, you’ll help break down, clean, and prepare the boat for the night.

What We’re Looking For:

No Experience Necessary: A love for the Chesapeake Bay, a friendly demeanor, and a willingness to learn are more important than prior experience.

Physical Ability: You must be able to pull up a very heavy sail and be comfortable walking on deck aboard a sailboat.

Customer Service Focus: Smile and a friendly disposition are a must. Our reputation for excellent customer service means we are looking for someone who enjoys interacting with people and making their day special.

Team Player: You’ll be part of a small but passionate crew, so being a team player is key.

Details:

Location: St. Michaels, MD – a charming town on the Chesapeake Bay.
Schedule: 5 daily 2-hour trips, with up to 6 guests per trip. You’ll get a variety of opportunities to interact with different groups and contribute to their unique experience.
Pay: Competitive wages plus split tips.
Start Date: Seasonal (April through early Nov), with potential for future opportunities.
Read Our Reviews: We are known for our incredible customer service—check us out on TripAdvisor to see how our guests rave about their experiences!

Ready to Join Us?

If you’re friendly, outgoing, and excited about helping create magical moments for guests while learning the ropes aboard a historic sailboat, we want to hear from you! Send us a message with basic information about who you are, why you want this position, and what makes you a great addition to our team. For more info, check out our website at [blocked].

Want to connect? you can call Capt Iris [blocked] or email us at [blocked] We can’t wait to meet you!

show hide Position

Position

  • Crew positionDeckhand

  • Type of workTemporary / Seasonal

  • Availability 15 Apr 2026 until 3 Nov 2026

  • Salary $base stipend plus split tips

  • Expenses to/from vesselPaid by crew

  • Expenses onboardPaid by crew

  • Team / SoloNot important

  • InterviewPhone interview
    We will arrange a date and time that is convenient for us both

show hide Vessel

Vessel

  • TypeSailing Yacht

  • Make/model42' ketch

  • Length42 feet

  • Berth12

  • Sailing from United States , St Michaels MD

  • Sailing to Local sailing , St Michaels MD

  • Language spoke aboardEnglish

  • Boat descriptionLady Patty offers an authentic monohull sailing experience aboard a beautifully restored 1935 2-masted ketch sailboat. Originally designed for offshore racing, she features original style wooden masts, sails, and rigging. The captain steers the vessel from the stern and the mate assists by controlling the sails as well as interacting with the guests and serving beverages. There is ample cushioned seating for all guests, but space and opportunity to lay down or walk around during the sail may be limited. Guest access to the cabin area is limited to emergency use of the head (restroom). Crew would assist with raising the sails and docking as well as serving the guests and making sure they have a great experience. We have our liquor license so alcoholic beverages will be purchased by guests.

show hide Skipper

Skipper

  • NationalityUSA

  • Age45

  • GenderMale

  • Fluent languages English

  • Qualifications USCG Captains License

  • Sea Miles 10,000+

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