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  • SailSelina

    • 41ft 41' Gaff rigged CatBoat
    • United States
    • Checked in 21 hours 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 2025 until 3 Nov 2025

  • 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/model41' Gaff rigged CatBoat

  • Length41 feet

  • Berth0

  • Sailing from United States , St Michaels MD

  • Sailing to Local sailing , St Michaels MD

  • Language spoke aboardEnglish

  • Boat descriptionAbout the Vessel: Selina II Step aboard the Selina II, a living piece of history, and you’ll quickly realize this is not just any boat—it’s an iconic 1926 historic gaff-rigged catboat that has been a beloved part of the Chesapeake Bay for nearly a quarter of a century. As a deckhand on this vessel, you’re not just working on a boat; you’re helping to preserve maritime heritage while offering guests an intimate, unforgettable sailing experience. With a sleek wooden hull and elegant lines, Selina II offers a classic sailing experience in one of the most beautiful and serene locations in the country—St. Michaels, Maryland, nestled on the stunning waters of the Chesapeake Bay. Limited to just six guests, this vessel provides an exclusive, personal experience that makes every voyage feel special. As a crew member, you'll get the chance to engage with guests from all over the world, offering them a unique, hands-on experience aboard this beautiful classic boat. The boat’s historic charm is paired with modern amenities that make her a dream to sail. Whether you're helping raise her heavy sails, guiding guests through the daily operations, or polishing the brass that glimmers in the sun, every task on the Selina II is part of something greater—a team effort to create lasting memories for our guests. This is more than a job; it’s an opportunity to learn from seasoned sailors and share your passion for the water with others. As a crew member, you’ll have the chance to truly connect with the boat, the Bay, and the people who make the experience so memorable. Every sail is a new adventure, and every day brings the chance to be part of something historic, intimate, and enriching. Oh! and she is everything we just described, but I should also mention she is very wide and very stable, so a super smooth ride. But not fast. If you have a need for speed this is not your gig.

show hide Skipper

Skipper

  • NationalityUSA

  • Age66

  • GenderFemale

  • Fluent languages English

  • Qualifications USCG Captains License

  • Sea Miles 10,000+

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