The years following the war saw a period where Dylan strived to emigrate to America. Symptomatic of a lifetime seeing the grass greener elsewhere, his departure from Swansea, "a dingy hell", for the freedom of London only highlighted his fondness for this "ugly, lovely town". The war had left Swansea a mere shell of its former self and this undoubtedly upset Dylan. After the raids of Swansea's "Three Nights Blitz" he surveyed the still-smoking town centre with his literary friend Bert Trick and proclaimed, clearly distressed, "Our Swansea is dead". His nostalgia for the town he had turned his back on was later explored in his auto-biographical short story "Return Journey". In 1990, this tale was made into a film directed by Sir Anthony Hopkins.

Although Dylan was becoming increasingly well-known for his poetry and frequent BBC broadcasts, he never seemed to earn enough money to support his family, or pay his crippling debt to His Majesty's Inspector of Taxes - who had discovered by 1948 that Dylan had never made a single tax return. Looking, as always, for a place for him and his family to settle, it is rumoured that Dylan had considered renting the Old Rectory house at Rhossili, but due to financial pressure he finally accepted the gift of the Boat House at Laugharne from his friend Margaret Taylor.

Dylan's first trip to America was fuelled by the invitation of Irish poet and critic John Malcolm Brinnin to give lectures on poetry. The tour was a success but Dylan again succumbed to the heady world of liquor and women. Whilst in New York he met a woman with whom he entered a year long affair. Dylan's wife, Caitlin, though discovering the affair, saw her marriage through to the bitter end, but the trust was never to return to their relationship. The following years saw a repeat of this scenario. Dylan toured America, drinking himself into oblivion, made a social spectacle of himself and pursued women until he was forced to return to Laugharne to recuperate. His health was becoming increasingly undermined and the trips to the US were certainly not helping. Unfortunately, Dylan's debts forced him to take advantage of the money he could earn touring. Dylan's final stay in Swansea was in October 1953, where he resided at The Bush Inn. From here, he traveled to London and then to America to direct the rehearsals for an enlarged version of 'Under Milk Wood'. During this visit he suffered terrible blackouts and trembling episodes caused by the damage to his body by alcohol. After a final drinking binge on the night of 3 November, in the New York's tavern The White Horse, Dylan fell into a coma which was to end his life on 9 November. Caitlin returned his body to Laugharne where he was laid to rest.

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Despite Dylan's often shady life, he was also a great man and arguably Wales finest poet and author - a man whose literary stature in the world seems to increase with each passing year. To honour Dylan, Swansea has kept the poet's memory alive outside of his books with a plethora of statues and commemorative works and even a entire Centre devoted to him.