We’re Hiring Our Wine Sail Assistant

Who wants to hang out with us on all wine sails with us 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, Saturdays, and most Sundays, June 10 – October 9 with two wine sails daily. You can see the wine schedule here and more details on working hours below. We’re looking for someone who can think independently, be punctual, and can 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 look forward to hearing from you.

More details

Must haves:

  • Strong written and verbal 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

What do you need to succeed?

  • Dependable transportation

  • Ability to stand for two or more consecutive hours 

  • Computer and mobile phone/text use

  • Ability to lift up to 50 lbs 

  • Experience with Square, Squarespace, and hospitality is a plus

  • Strong/photography Social Media skills are a plus

What will you do in this role?

  • Work part-time (14 - 21 hours per week) Fridays, Saturdays, and most Sundays (with the last Sunday of the month off)

    • June 10 - August 31, 2:00 PM – 9:00 PM

    • September 1 - September 30, 12:00 PM – 7:00 PM

    • October 1- 9, 11:00 AM – 6:00 PM

  • Assist with wine sail set up, including preparing cheese plates, and opening wine bottles prior to wine sail departure

  • Distribute glassware, handouts, and cheese plates 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