Othello met Ser Darron and Gregoriy in a brothel barge in Planky Town in 287 AC. Othello was keeping company with Oberyn Martell and when the newcomers asked about his services he explained he was already contracted to take Oberyn to Vaith. After some terse words were exchanged Obara entered complaining of boredom. She challenged the newcomers to a series of feats, and if bested she would convince her father to relinquish his contract with Othello. Othello saw no reason to object and agreed.

After Ser Darron bested Obara in two of the three contests Othello kept his word and his barge, laden with tools and materials, left Planky Town bound for the Rambis. Darron and Ezzelina made the return trip along the coast of Dorne with Othello while the others returned with the horses via land. Upon their arrival, Othello and his crew set about the work of repairing the vessel’s hull, which was so damaged that a horse could pass through the hole.

Arianne and Sylva stowed away on the Rambis during its sea trial, following the repairs to its hull made by Othello. They were discovered their by Lord Teddy Jasper. During questioning both girls revealed an interest in adventure. After hearing that Teddy enlisted their help in rescuing Ser Dolins and their friend Thomas from captivity at the hand of the Ironborn. Othello witnessed the agreement but took no part as it was not his place to speak amongst lords, ladies, and princesses.