Medina Bookshop in Cowes is to host the launch of a remarkable new sailing memoir on Tuesday 18th August 2026, when Isle of Wight-based author and sailor Jenny Whelan celebrates the publication of Dogsail: Sailing round Britain with a Dog, a Chatbot, and a Swedish Viking.
Island
An unconventional crew
The book tells the story of an extraordinary 130-day, 1,800-mile circumnavigation of Britain, undertaken by a decidedly unconventional crew: Jenny, her Swedish partner Pete, their large Bernese Mountain Dog Svea – and an AI chatbot.
The voyage began with Pete’s determination to fulfil a long-held ambition to sail around Britain. Jenny, an experienced offshore sailor, joined him aboard their Westerly Fulmar, along with Svea, a much-loved dog who was raised aboard the boat. The fourth member of the crew was an unlikely one: an AI chatbot, consulted along the way for advice and assistance.
The resulting voyage took them around some of Britain’s most spectacular and challenging coastline, bringing encounters with strong tides, difficult weather, unfamiliar harbours and the everyday realities of living aboard a small yacht with a very large dog.
More than a sailing story
But Dogsail is about much more than sailing. It is a story of friendship, resilience, companionship and adventure, with the added curiosity of exploring what happens when traditional seamanship meets artificial intelligence.
Jenny Whelan brings considerable sailing experience to the story. A former Metropolitan Police detective, she is now a sailing instructor based on the Isle of Wight and has competed in events including the Fastnet Race and the Caribbean 600. In 2025, she and Pete set off on their remarkable voyage around Britain with Svea.
The book has already received an enthusiastic endorsement from renowned sailor and author Tom Cunliffe, who describes it as “A barking good read. A must for all sailors and dog-lovers.”
Meet the author
The launch at Medina Bookshop will be a relaxed celebration of the publication of Dogsail, rather than a formal author talk.
Guests will be invited to raise a glass with Jenny, celebrate the book’s arrival and meet the author. There will also be the opportunity to buy copies of Dogsail and have them signed.
Why it matters for the Woof Awards
And if you needed another reason to come along, the event is also a fine example of why Medina Bookshop deserves your vote in the Red Funnel Woof Awards.
The bookshop’s programme of author events regularly brings writers, musicians and some wonderfully unusual stories to Cowes – and what could be more appropriate for a Woof Award than celebrating the launch of a book whose star is a very large, seafaring Bernese Mountain Dog?
Whether you’re a seasoned sailor, a dog-lover, curious about life at sea, or simply intrigued by the idea of an AI chatbot joining a voyage around Britain, everyone is welcome to come along and celebrate the launch.
Where and when
The book launch of Dogsail takes place at Medina Bookshop, 50 High Street, Cowes on Tuesday 18th August 2026 from 6pm.
Drinks will be served and copies of Dogsail will be available to purchase and sign.
News shared by Paul on behalf of Medina Bookshop. Ed
