We’re Hiring!

Wine Sail
Assistant
Saturdays

Part-time, SEASONAL
Portland, Maine

Who wants to hang out with us on our highly-rated wine sails this summer? We’re hiring two assistants to Sommelier Erica Archer for our very frequent and very awesome wine sails in Portland, Maine. As the Wine Sail Assistant, you will assist with all wine sail activities before, during, and after sailing aboard the beautiful sailboat Frances, built by her Captain and crew in Portland, Maine, and 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 set on exceeding customer expectations by providing the best quality, customer service, and experience possible. 

The schedule is Saturdays, June 13 – October 19, with two-three wine sails daily. We’re looking for someone who can think independently, be punctual, carry cases of wine (32-50 lbs), be great with customer service, and be able to work on a large moving boat. We need someone that is 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 than a glass-half-empty person. No experience is necessary. We’ll train the right person. It’s very easy and very fun!

TO APPLY

Please email winewise@winewiseevents.com with your cover letter and resume with “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. In your cover letter, be sure to include your interest in working Saturdays as well as any other available dates. We’re only able to respond to applicants who provide both documents 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?

  • Work part-time (7 - 12 hours per week) on the following schedule:

    • June 13 - July 31

      • Saturdays 2:15 PM – 9:00 PM

    • August 1 - August 31

      • Saturdays 2:00 PM – 8:30 PM

    • September 1 - September 30

      • Saturdays 12:30 PM – 7:15 PM

    • October 1- October 19

      • Saturdays 11:00 AM – 5:30 PM

    • There will be select days throughout the season when optional shifts may be available on Mondays through Thursdays, as well as some Fridays and Sundays.

  • Assist with wine sail set up, including preparing cheese boxes, opening wine bottles, and customer service before departure

  • Distribute handouts, plates and cheese boxes during the wine sail 

  • Collect glassware and plates from passengers at the end of the 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 and the boat dock and the boat

  • Have fun!

  • Take a 15 minute break in-between wine sails