We’re Hiring!

Relief Wine Sail
AssistantS

FREELANCE HOURS VARY (SEASONAL)
Portland, Maine

Who wants to hang out with us on our highly-rated and very awesome wine sails in Portland, Maine, this July through October? We’re looking for 2-3 “relief” Wine Sail Assistants to cover time off for our current team members. This could evolve into a more set schedule for the right person. As a “relief” Wine Sail Assistant, you will assist with all wine sail activities before, during, and after sailing aboard the beautiful tall ship Frances, docked on the Maine State Pier.

You’ll enjoy views of Maine’s lighthouses, waterways, and islands, all while caring for customers and learning a lot about wine. This is a dream job for the right person. We are committed to exceeding customer expectations by providing the highest quality, exceptional customer service, operational excellence, and an unparalleled experience. 

The schedule could include some Friday, Saturday, and Sunday shifts through October 19, with 2-3 Wine Sails offered daily. We’re looking for individuals who can be punctual, carry cases of wine (32-50 lbs), provide excellent customer service, follow operating procedures, work effectively on a large moving boat, and be 100% reliable.

We’re not concerned with you knowing wine. We’d rather you be great at customer service and hospitality, reliable, on time, and solid! And be a glass-half-full person rather than a glass-half-empty person. No experience is necessary. We’ll train the right person. It’s very easy and a lot of fun!

TO APPLY

Please email winewise@winewiseevents.com with your cover letter and resume with “Relief Wine Sail Assistant (Part-Time) at Wine Wise” in the subject line. Please be sure to submit both a resume, which outlines your relevant experience, and a cover letter, which shares your enthusiasm for the role and explains why you believe you're a great fit for this exciting opportunity. Additionally, in your cover letter, please specify the days and hours you are available to work, as well as any days and dates you are unavailable. We all need time off, so being upfront here is valued. We’re only able to respond to applicants who provide both documents with the completed information and who appear to be a strong match for our current needs.

We look forward to hearing from you!

More details

Must haves:

  • Strong communication skills

  • Attention to detail and ability to think on your feet 

  • Able to work on a large boat (does not get seasick) 

  • Punctuality and dependability

  • Initiative, accountability, and time management skills

  • Able to be a strong asset to a team

  • Dependable transportation

  • Ability to stand for two or more consecutive hours 

  • Computer and mobile phone/text use

  • Ability to lift and carry up to 50 lbs

Not required, but a plus:

  • Experience with or a willingness to learn hospitality

  • Strong video, photography, and Social Media skills or a willingness to learn

What will you do in this role?

  • Cover open shifts that may occur on the following schedule:

    • June 13 - July 31

      • Fridays: 2:15 - 5:30, 5:30 - 9:00

      • Saturdays: 11:00 - 2:15, 2:15 - 5:30, 5:30 - 9:00

      • Sundays: 11:00 - 2:15, 2:15 - 5:30, 5:30 - 9:00

    • August 1 - August 31

      • Fridays: 2:00 - 5:15, 5:00 - 8:30

      • Saturdays: 11:00 - 2:15, 2:00 - 5:15, 5:00 - 8:30

      • Sundays: 11:00 - 2:15, 2:00 - 5:15, 5:00 - 8:30

    • September 1 - September 30

      • Fridays: 12:30 - 3:45, 3:45 - 7:15

      • Saturdays: 12:30 - 3:45, 3:45 - 7:15

      • Sundays: 12:30 - 3:45, 3:45 - 7:15

    • October 1- October 19

      • Fridays: 11:00 - 2:15, 2:00 - 5:30

      • Saturdays: 11:00 - 2:15, 2:00 - 5:30

      • Sundays: 11:00 - 2:15, 2:00 - 5:30

    • There will be select days throughout the season when optional shifts may be available on Mondays through Thursdays.

  • Assist with wine sail setup, including preparing cheese boxes, opening wine bottles, and providing customer service before departure.

  • Distribute handouts, plates, and cheese boxes during the Wine Sail.

  • Collect glassware, plates, and trash from passengers at the end of each Wine Sail.

  • Serve food pairings prepared by local chefs or fresh-shucked oysters to Wine Sail passengers.

  • Help in transporting wine sail supplies, including cases of wine, to and from the Maine State Pier, to the boat, and then back.

  • Have fun!