We’re Hiring a Seasonal Wine Sail Assistant

Who wants to hang out with us on our highly-rated wine sails this summer? We’re hiring an assistant 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 Fridays and Saturdays June 7 – October 13 with 1-3 wine sails each day. Please see the working hours below. 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. We’d rather you be 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!

If you think you are the right person, we’d love for you to apply. Please email your resume and cover letter to winewise@winewiseevents.com. If you could put Wine Sail Assistant Application in the subject line, that would be great, too! It’s important to send both a resume (which tells us what experience you have) and your cover letter (to tell us what desire you have and why you think you are the best person for this very awesome job). We are only able to respond to applicants who submit both.

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: Square, Squarespace, and hospitality

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

More Open Positions: We are also hiring two people for social media positions for Wine Wise (seasonal and/or year-round) and Portland Wine Week (January - June). If you have social media experience, and/or a strong willingness to learn, we could combine the Wine Sail Assistant and Social Media positions into one.

What will you do in this role?

  • Work part-time (10 - 16 hours per week) on the following schedule:

    • June 7 - July 31

      • Fridays 2:00 PM – 5:30 PM

      • Saturdays 11:00 AM – 9:00 PM

    • August 1 - August 31

      • Fridays 2:00 PM – 5:30 PM

      • Saturdays 11:00 AM – 8:30 PM

    • September 1 - September 30

      • Fridays 3:45 - 7:15

      • Saturdays 12:30 PM – 7:15 PM

    • October 1- October 13

      • Fridays 3:45 - 7:15

      • Saturdays 11:00 AM – 5:30 PM

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

  • Distribute glassware, handouts, 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 break in between wine sails