We’re Hiring!
Oyster shuckerS

Part-time, Freelance, SEASONAL
Portland, Maine

Calling skilled oyster shuckers! Want to shuck fresh Maine oysters while sailing through Casco Bay aboard a 74-foot sailboat? Join us for a summer and fall of unforgettable experiences on our highly rated Wine & Oyster Sails—set aboard the beautiful Frances, a traditional tall ship built by her captain and crew in Portland, Maine, and docked at the Maine State Pier.

We’re looking for two fast, reliable, and professional Oyster Shuckers to join our seasonal team for five Wine & Oyster Sails, June 12 - October 18. This role requires precision, speed, and a deep respect for handling seafood safely and beautifully. You’ll be shucking oysters for guests while sailing past lighthouses, islands, and historic forts—maintaining high standards of professionalism and safety.

This is a dream job for the right person. We’re focused on exceeding customer expectations, and we need people who are solid, trustworthy, punctual, skilled, and 100% reliable.

We have 25 Wine & Oyster Sails on the 2026 schedule, with most covered. The following opportunities are currently available. Plus, we will be adding many more.

Season Details:

  • June 12 – October 18

  • Wine & Oyster Sails schedule (some, not all shifts need coverage, and we will be adding more)

  • Each sail lasts about 2 hours, plus 1.5 hours of setup and breakdown time

Current Opportunities:

  • Open Wine & Oyster Sail shifts:

    • Fri, JUN 12, 2:15 - 5:45 PM

    • Fri, JUL 3, 11:00 - 2:30 PM

    • Fri, JUL 10, 11:00 - 2:30 PM

    • Fri, SEP 4, 12:30 - 4:00 PM

    • Mon, SEP 7 12:30 - 4:00 PM

    • Fri, OCT 2, 11:00 - 2:30 PM

  • Open Wine & Oyster Tasting Events:

    • Thu, JUN 4, 1:00 - 8:30 PM

    • Wed, JUL 15, 4:00 - 8:00 PM

    • Wed, AUG 5, 4:00 - 8:00 PM

Plus, we will be adding many more, based on availability.

Top Qualifications:

  • Proven oyster shucking experience (this is not an entry-level role)

  • Comfortable standing for 2+ hours and working on a moving sailboat (must not get seasick)

  • Reliable and punctual

  • Familiarity with Maine oyster varieties

  • Strong knife skills and attention to safety and cleanliness

  • Ability to lift and carry up to 50 lbs

  • Dependable transportation

  • Ability to communicate reliably by email and text (Mobile phone number)

Key Responsibilities:

  • Shuck and serve oysters quickly, cleanly, and with pristine presentation

  • Handle oysters and tools with care, following food safety guidelines

  • Inspect oysters for quality and freshness before serving

  • Maintain a clean, sanitary, and organized shucking station at all times

  • Work safely and steadily on a large, moving sailboat

  • Engage with guests about oyster varieties when appropriate

  • Set up and break down oyster station for each sail

  • Pick up oysters at Upstream and transport them to the dock (one pier over)

TO APPLY
Email winewise@winewiseevents.com with your resume and the subject line: “Oyster Shucker for Wine Wise.” Include a brief note with:

  • Your oyster shucking experience.

  • Why you’re a great fit for this very awesome job.

  • Your availability and schedule limitations—please be thorough.

We are only able to respond to applicants who submit both and who we feel might be a match for our needs. We look forward to hearing from you.