We've named the winners of our 11th annual “Sail into Imagination” art contest! 

This year, more than 100 students in grades kindergarten through 12 submitted original artwork inspired by the theme “The Sea and Me.” Students were asked to share their connections to the sea and the Steamship Authority. Students attending schools on Cape Cod, plus residents of Martha’s Vineyard, Nantucket, Fairhaven, and New Bedford, were invited to participate.

Each winner will receive a $100 Steamship Authority gift card that can be used for travel, concessions, or parking. Also, student Emily Majkowski of the West Tisbury School in Vineyard Haven has been selected as the winner of a $150 Visa gift card in a grand prize drawing open to all entrants in the contest.

A big thank you to Benton Jones, director of art at the Cape Cod Museum of Art, for judging the art submissions. 

The 2027 calendar winners, including their name, grade in the 2025-2026, and school are listed below. All the winning art may be viewed at https://bit.ly/2027SSAcalendar.

Ismail Almasroori

Barnstable United Elementary School, Barnstable, Grade 5

Max Couillard

Morse Pond School, Falmouth, Grade 6

Helen Faye

Morse Pond School, Falmouth, Grade 6

Lillianna Grillo

West Tisbury School, West Tisbury, Grade 4

 

Isabella Iannitelli

Morse Pond School, Falmouth, Grade 6

 

Kayla Karchner

Morse Pond School, Falmouth, Grade 6

Isabella Kowal

Greater New Bedford Regional Vocational-Technical High School, Grade 10

Kirill Kren

Nantucket Intermediate School, Nantucket, Grade 4

Rose Lopes

Oak Bluffs Elementary School, Oak Bluffs, Grade 2

Adyson McCarthy

Sandwich Middle-High School, East Sandwich, Grade 7

Zoe McNeil

East Fairhaven Elementary School, Fairhaven, Grade 4

 

Boonraksa Montoya

Chilmark School, Chilmark, Grade 3

Addison Seger

West Tisbury School, West Tisbury, Grade 4

Abigail Smith

Home Schooled (Nantucket), Grade 7

Leah Smith

Home Schooled (Nantucket), Grade  9