Anne of the Island is the third book in the Anne of Green Gables series following the adventures of its heroine Anne Shirley as she leaves for Redmond College in the busy city of Kingsport to study for her bachelor’s degree. The third installment in the series sees the beloved protagonist experience new adventures and challenges outside the familiar setting of Avonlea. The novel kicks off when Anne decides to pursue her dream of a higher education, and subsequently leaves her two year teaching position at the school in Avonlea and begins her studies at Redmond College. Fortunately, Anne is not alone in the new environment, as she is accompanied by her old friends Gilbert Blythe, who has also enrolled in Redmond College, as well as roommates Priscilla, Philippa and Stella. Though Anne has her mind set on good grades and flawless academic prosperity, she cannot avoid the tides of love and the many suitors offering their affection. When Anne rejects Gilbert’s proposal, stating that she only views him as a friend, she must undergo a journey of self-searching and discover the true meaning of love. Striving for a true love resembling those from the many books she has read, Anne must draw the line between fiction and reality, or she might miss her only chance at happiness. Montgomery’s third installment can be considered to be a turning point in Anne’s life as the novel brings new problems and important decisions to be made, which in turn will either make or break her. Womanhood, maturing, and love are just some of the themes explored in this classic. A novel depicting the inevitable process of growing up, Anne of the Island is a perfect illustration of the challenging and sometimes awkward moments we all go through to achieve our full potential in life.
Anne leaves Green Gables and her work as a teacher in Avonlea to pursue her original dream (which she gave up in Anne of Green Gables) of taking further education at Redmond College in Nova Scotia. Gilbert Blythe and Charlie Sloane enroll as well, as does Anne's friend from Queen's Academy, Priscilla Grant. During her first week of school, Anne befriends Philippa Gordon, a beautiful girl whose frivolous ways charm her. Philippa (Phil for short) also happens to be from Anne's birthplace in Bolingbroke, Nova Scotia.
The girls spend their first year in boardinghouses and decide to set up house thereafter in a lovely cottage called Patty's Place, near campus. Meanwhile, Anne's childhood friend Ruby Gillis dies of consumption (tuberculosis) very soon after finding her own true love. The girls enter their second year at Redmond happily ensconced at Patty's Place, along with Queen's classmate Stella Maynard and her "Aunt Jimsie" (their chaperone), while life continues in Avonlea. Diana Barry marries Fred Wright and Davy and Dora continue to keep Marilla busy.
Midway through their college years, Gilbert Blythe, who has always loved Anne, proposes to her but Anne rejects him; although she and Gilbert are very close, she holds sentimental fantasies about true love (all featuring a tall, dark, handsome, inscrutable hero) and does not recognize her true feelings for Gilbert. Gilbert leaves, his heart broken, and the two drift apart.
Anne later welcomes the courtship of Roy Gardner, a darkly handsome Redmond student who showers her with attention and poetic gestures. However, when he proposes after two years, Anne abruptly realizes that Roy does not really belong in her life, and that she had only been in love with the idea of him as the embodiment of her childhood ideal.
Anne is so ashamed in how she treated Roy that she feels her entire Redmond experience may have been spoiled. She returns to Green Gables, a "full-fledged B.A.", but finds herself a bit lonely. Diana gives birth to her first child, and Jane Andrews, an old school friend, marries a Winnipeg millionaire. Having received an offer to be the principal of the Summerside school in the fall, Anne is keeping herself occupied over the summer when she learns that Gilbert is gravely ill with typhoid fever. With shock, Anne finally realizes how deep her true feelings for Gilbert are, and endures a white night of fear that he will leave this world without knowing that she does care. In the morning, Anne gratefully learns that Gilbert will survive. Gilbert recovers over the summer, bolstered by a letter from Phil assuring him that there is really nothing between Anne and Roy. After several visits to Green Gables, Gilbert and Anne take a late summer walk in Hester Gray's garden, and finally become engaged.
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