Having seen so much in Rome of the incompetence and frivolity of literary people, he despaired of finding due appreciation for the elaborate finish which it was his ambition to bestow upon his productions and without which he did not care to write. But still his ambitious spirit commanded him to persevere, and among the signs of encouragement he received was the homage paid him by Niebuhr of the dedication of one of his works. When Niebuhr left Rome he enjoined upon his successor Bunsen to value the great merit of Leopardi, and Bunsen proved himself the poet's friend through life.

In 1825 he received an offer from the Milanese publisher Stella to superintend an edition of the complete works of Cicero and to reside with him while the sheets were passing through the press. He gladly accepted. He set out for Milan in July, staying at Bologna for a month to avoid the fatigue of travelling during the great heat. Bologna was one of the few places that he really liked. He enjoyed the company of Giordani and other friends, and he was loth to part with them. When he reached Milan, he pined to return to Bologna; everything seemed to him repulsive and even hostile; he made no friends; his duties with regard to the edition of Cicero seemed to him intolerably irksome; and he even disliked the gaieties of Milan, gaieties in which he was at times too unwell and at other times too melancholy to join.

"He carried with him his misfortune wherever he went," says Ambrosoli, who met him at this epoch; "and he could not remain happy for long in any place. He could not obtain any suitable post in Italy, and out of Italy he would not accept one. When in 1825 he came to Milan to stay some months with the publisher Stella, he was already an object of compassion, so young, and with such a reputation for genius and learning, and yet visibly hastening to his end. In his conversation, as well as in his writings, he was so simple, so remote from any ostentation, that few might suspect that he was an extraordinary man; but by degrees the flashes of his wit and the treasures of his knowledge revealed the powers within him."

At last he carried out his intention of returning to Bologna, but the second visit was not so pleasant as the first. When the winter came, it was bitterly cold, and his health suffered in proportion. He would willingly have returned to Milan, but he did not receive another invitation. He was occupied with a Commentary on Petrarch, a labour which he did not undertake very readily, but which was pressed upon him by Stella. It was a great success, and Stella had reason to congratulate himself upon his acumen in getting the work done by so gifted a writer. He entrusted Leopardi with the editing of a selection from the best works of the best authors, and this task was still occupying him when he returned to Recanati, in November, 1826.

It would appear that during his sojourn at Bologna he had not been insensible to the attractions of love; but love could be for him nothing but a source of torment; and as his first return home was signalised by the wreck of hope, so was his second by the blighting of affection. He seemed, like the hero of the Pilgrim's Progress, to be writhing in the grasp of Giant Despair; and from the day of his arrival to that of his departure, in the following April, he was not once seen in the streets of Recanati.

He sought a remedy for his sorrows by returning to Bologna, but in vain; and on the 20th of June, 1827, he removed to Florence where he enjoyed the society of Giordani; but an acute inflammation of the eyes confined him to the house and long prevented him from inspecting the treasures of art that overflow the Tuscan city. At this epoch he published his Operette Morali, a series of dialogues and essays, offering, according to the best critics of his country, the most perfect specimen of prose in the Italian language.

In the autumn he somewhat recovered, and wishing to continue the improvement, he avoided the cold of Florence by wintering at Pisa. Florence, as a residence, he did not like, but with Pisa he was enchanted. The improvement, however, was but slight, and his nerves were in such a weak state that any sort of application or study was out of the question. In April, 1828, he was able to apply himself again to composition, and he seemed to be reviving, when the death of his brother Luigi afflicted him profoundly. From June to November he was again at Florence, but his yearning for home made itself felt after the recent bereavement.

He started on the 12th of November for Recanati in the company of a young man afterwards known to fame as Vincenzo Gioberti. He found his birthplace darkened by the shadow of death, which seemed to him the herald of his own. His former gloom returned, but in a more terrible shape; he saw only annihilation before him; and he took the last glance of life in his superb Ricordanze, the most richly coloured, the most deeply pathetic, the most unfathomably profound of all his poems.

In 1830, his Florentine friends, wishing to have him once more in their midst, urged his return to their city. Accordingly, in May he took leave of his family, little thinking he should never see them again. It would be curious to enquire what made him so wretched when at home, and yet, when absent, always longing to be there. His brother Carlo said many years later to Prospero Viani, the editor of his correspondence, that none of his poems written elsewhere had the beauty of those composed at Recanati; and when Viani mentioned the Ginestra, Carlo replied that in substance even the Ginestra was conceived at Recanati. Some biographers say the Risorgimento was written at Pisa; but Ranieri, who was probably well-informed, says it was written at Recanati, and this assertion is, I think, borne out by internal evidence. The Canto Notturno seems also to have been written in his birthplace. Thus, Carlo's statement would be correct. It is observable that the poems subsequent to the Canto Notturno, with the exception of Aspasia and the little poem To Himself, have an air of languor, foreign to his earlier productions. This languor is perceptible even in the sublime Ginestra, and it is not absent from passages of the Pensiero Dominante, Amore e Morte, and the long, mock-heroic Paralipomeni. The repose, sepulchral as it may have seemed to him, of Recanati, and the exquisite beauty of its scenery, bordered in the distance by the blue waters of the Adriatic, were conducive to the exercise of the imagination. Nor must we forget that he spoke of other places (except Pisa and Bologna) with equal bitterness. The climate seems really to have worked havoc on his delicate frame. He allowed its inhabitants only one merit, that of speaking Italian with purity and elegance.

His stay in Florence, which extended from May, 1830, to October of the following year, was made memorable by the publication of another edition of his Poems, with many pieces added and with a dedicatory epistle to his Tuscan friends. At this period, he made the acquaintance of Ranieri, a Neapolitan with literary talents, who was to be his intimate friend and future biographer.