After surveying society on both sides of the Atlantic, Henry James declared Margaret Terry “Daisy” Chanler the only truly cultivated woman in America. Bernard Berenson worried it would take generations for the world to see someone like Daisy again. “There was something expansive, generous, radiant about her, and a perpetual adolescence of mind that made her eager for contact with . . . the upper reaches of recent but already consecrated literature and art,” he wrote in his diary after her death. He remembered her as “a great reader, in German as well of course as in Italian and in French, she was like Edith Wharton, with whom one could discuss any book of European interest.” With her husband, the Rough Rider Winthrop Astor Chanler (“Wintie” for short), she appeared on Ward McCallister’s list of The Four Hundred members of New York high society. Without a formal education, she was fed good literature and good music by governesses and tutors. Well traveled, she lived in Rome, New York, and Washington, discovering everywhere the company of delightful people. A woman of true taste, not mere snobbery, during her long life Daisy cultivated friendships with James, Wharton, Teddy Roosevelt, Henry Adams, Franz Liszt, Edward Lear, George Gershwin, and more.

A woman of true taste, not mere snobbery.

Henry James overheard in Rome the conversation that inspired Daisy Miller, his breakout success. The Eternal City was also the oyster bed that cultivated young Daisy Chanler. Her father was the expatriate American artist Luther Terry, and she lived with her family on the second floor of the Palazzo Odescalchi. Behind the colossal facade designed by Bernini, the empty ballroom was an ideal playroom. The Odescalchi claimed as an ancestor one of the Three Kings, Balthasar, who gave the Christ Child the gift of frankincense, and their doorknobs were shaped like incense boats. The ballroom walls were lined with arabesques of Indian silk and “those dim, eighteenth century mirrors which reflect the light very softly and seem to hold the shadows of things long past.” The children dangled their feet through the bars of the ballroom’s French windows practicing the classic Roman pastime of stare in finestra—to stay at the window and watch the street life below. They would look out for their father walking back from his studio on the Via Margutta, often carrying violets bought at a street stall in the Piazza di Spagna. Funeral and wedding processions from the nearby Church of the Twelve Apostles were a highlight. Daisy remembered the magnificent funeral of the Duke of Tuscany. To the long line of monks, Knights of Malta, and ambassadors, the Roman Senate added three glass coaches, each steadied on the cobblestones by four footmen holding silken cords and wearing knee breeches.

Edith Wharton writes in her autobiography that, from her childhood memories in Rome, “only Daisy and her brother have remained alive to me. . . . There we played, dodging in and out among old stone benches, racing, rolling hoops, whirling through skipping ropes, or pausing out of breath to watch the toy procession of stately barouches and glossy saddles-horses.” The children enjoyed special access to the Quirinal Garden and buried a pet canary underneath the pope’s box hedges.

The Terrys were Episcopalians, but on rainy days they went to St. Peter’s for exercise. In the era of the Papal States, crowds had not yet overwhelmed the great basilica. Then, as now for millions of tourists, the gilded skeleton of Bernini’s tomb for Alexander VII made a lasting impression on the children, extending a bony hand holding Death’s hourglass from beneath carved jasper drapery.

Daisy’s half-brother was the prolific novelist F. Marion Crawford, a nephew of the author of “The Battle Hymn of the Republic,” Julia Ward Howe. After Marion’s father died, his mother married Luther Terry and gave birth to Daisy. Before she entered the Astor ballroom stateside, Daisy enjoyed the delights of the Roman social season, which ran from Christmas until Shrove Tuesday, accommodating the liturgical year. Dances were never scheduled during Advent and Lent. Marion records the scene of the Orsini Ball in his novel Saracinesca:

In the reception-rooms there was much light and warmth; there were bright fires and softly shaded lamps; velvet-footed servants stealing softly among the guests, with immense burdens of tea and cake; men of more or less celebrity chatting about politics in corners; women of more or less beauty gossiping over their tea, or flirting, or wishing they had somebody to flirt with; people of many nations and ideas, with a goodly leaven of Romans.

Polite and polyglot, Daisy had a friend in every palazzo. Madame Uxkull, the wife of the Russian ambassador, had “the smallest waist and widest eyes in the world.” General de Charette was the unofficial patron saint of lost causes after leading the Papal Zouaves in their last stand against Garibaldi at Porta Pia. Donna Laura Minghetti, the wife of the Prime Minister, opened her salon only to Daisy and friends serious about music, not the sorts of superficial American teases vexing Mr. Winterbourne in Daisy Miller—“the queerest creatures in the world.” At her villa on the Tarpeian Rock, Daisy played duets with Madame Helbig, née Princess Schachowskoia. A stout six feet tall, the princess preferred to drag the piano forcefully to her lap rather than shift her seat. The princess introduced Daisy to Franz Liszt, who figured forcefully in her musical education during his small group lessons at the Sala Dante, tucked inside the support wall of the Trevi Fountain.

Like Daisy Miller, she had a talent for introductions. She collected virtuosos in the way many Astor women collected jewels. She attended the first performance of La Cavalleria rusticana and discussed the melodies of Verdi with Igor Stravinsky. At a Vanderbilt dinner, she conspired with Toscanini to fulfill her wish to hear him conduct Beethoven and Brahms. When Richard Strauss and his wife came to New York, Daisy gushed that she loved one of his early sonatas. “That, he implied with a muffled grunt, did not give me the right to an opinion: he had composed far more important things,” she writes in her musical autobiography, Memory Makes Music. “He was not ingratiating.” In Paris, she comforted Erik Satie after his contemporaries shunned him. He was just her type—“witty without presumption.” She also befriended the master teacher Nadia Boulanger, joining her many parties at 36 rue Ballu and mourning her sister Lili at an annual Requiem Mass. Daisy met a young George Gershwin shortly after the premiere of Porgy and Bess. She told him how much she enjoyed it and that she was going to hear it again. “Oh do please like it again,” he said appealingly.

Daisy was formed by a culture of spoken word. As a child, she was granted permission to stay up late to listen to the stories told by their visitor Augustus Hare, whose Walks in Rome is still a canonical guide for travelers. “It was not a case of listening, but almost of actual experience.” Their storyteller ordered the lights turned low, the door barred to servants, and the ladies prohibited from touching their needlework. “And in this crepuscular stillness he told us with nerve-wracking vividness of the Secret of Glamis Castle, or the terrible story of the Vampire” in his “curious, rather nasal voice which has an extraordinary variety of tone and pitch—as he neared the climax it would tremble, and break, and rise.” In 1870 on a summer holiday in the mountains south of Turin, Daisy’s family stayed at a former Carthusian monastery. The poet Edward Lear appeared at lunch one day. This “rosy, grey-bearded, bald-headed, gold-spectacled little old gentleman” sang “The Owl and The Pussycat” as they played in the old cloister. Every day on their luncheon plate, Lear surprised them with a page of a nonsense alphabet book he had illustrated overnight. An example: “C—The Comfortable Cow, who sat in her arm-chair, and toasted her own bread at the parlour fire.” He continued until they each had a complete whimsical set.

Back in America, her sister-in-law Margaret Aldrich Chanler remembered a typical rainy Sunday when the house party began reading aloud a novel after breakfast and finished it before train-time. “Both girls and men were in good voice,” she writes in her memoir, Happy Vista. “Those who returned from church were quickly told what had happened in the interval. ‘Will you please begin there?’” In her twilight years, Daisy asked visitors to read aloud Henry James novels. “Her eyes would close and she would sit so still that I would begin to wonder whether she hadn’t drifted off to sleep,” recalls Louis Auchincloss in Love Without Wings. “But never. In a moment she would raise an interrupting finger and suggest: ‘Would you mind going over that last sentence again? I think you haven’t found the central verb.’”

Polite and polyglot, Daisy had a friend in every palazzo.

Great literature formed the foundation of her informal education. Twice weekly in Rome, the entire family was tutored in Dante by Don Raffaelle Pagliari. He dressed like a French Abbé in black silk stockings, knee breeches, silver buckled shoes, and a tricorn hat. Over forty years, he acquired what Longfellow judged the greatest private collection of Dante’s works, which filled his modest apartment inside the Palazzo Gabrieli. At a rate of two lessons per canto, Daisy completed her study of The Divine Comedy in three years as “Dante’s poetry, his philosophy, his faith, sank very deep into my soul.”

Dante and Don Raffaelle taught Daisy how “never sated is/ Our intellect unless the Truth illume it,/ Beyond which nothing true expands itself” (Paradiso, Canto IV). Papal Rome illuminated for her the Catholic Church and the expansive “stream of life that has flowed for so many centuries past those same temples, arches of triumph, porticoes, and palaces,” where martyrs, confessors, and virgins lived, prayed, and died. One day when she was playing on the Pincian Hill, Pope Pius IX alighted from his glass coach, patted her Protestant head in sympathy, and promised to pray for her.

She judged the tiny Anglican community in Rome “jejune” and “infinitely tedious.” Daisy and Marion first fell under the spell of the Roman Church during the Office of Tenebrae at the Lateran Basilica. As the choir sang the Miserere in the fading light, one by one the burning tapers were extinguished on the altar, and the congregation waited silently as the smoke ascended to the height of what Henry James called the churchiest church in Europe. The silence was broken by the ritual slamming of books, ending the service and ejecting the pair onto the streets of Rome in a daze.

Marion became a Catholic during a trip to India and wrote to Daisy as she tried to resolve her religious doubts. After stating the evidence in favor of the Church’s claims, he reassured Daisy:

There remains the important question, of tenfold importance to a person of your tastes, “How far will confession interfere with my freedom of choice in reading, with my freedom of speech in conversation?” I need not tell you that you are right in asking the question. But first you ask whether I, who read the most modern books and think the most modern thoughts, am a good Catholic—in the sense of being a staunch adherent to the faith and a conscientious observer of prescribed duties, I answer: I am. I can find nothing in the Church at variance with the occasionally reliable results of modern science.

Friendship with the Chanlers provided a relaxing private retreat for men in the public life like Roosevelt.

The Terrys and the Chanlers were high church Episcopalians with many connections to the Oxford Movement and Anglo-Catholics at home and abroad. Wintie’s sisters attended Miss Elizabeth Sewell’s Oxford Movement school on the Isle of Wight, carrying back personal stories about John Henry Newman: “Henry was forever fussing about authority.” In Boston, the Terrys enjoyed the society of Isabella Stuart Gardner and “her unscrupulous flirtations, her lavish extravagance, and her seasons of repentant piety.” Daisy remembers “Mrs. Jack” on Ash Wednesday dressed all in black with a large rosary hanging from her belt and on Good Friday on her knees washing the steps of the Church of the Advent run by the Anglo-Catholic Cowley Fathers.

Whether Wintie’s Harvard education reinforced or rent the veil of invincible ignorance is a question for moral theologians. He deferred religious matters to a later date, often telling his wife that he wished to die a Catholic, like her, but not until “my head is so far from the ground on my last fall,” as he would say while holding two fingers inches apart. His Episcopalian sisters were offended by the Roman legalism requiring proof of his baptism during his engagement to Daisy, but he was unperturbed. The Code of Canon Law required three dispensations to marry as cousins, during Advent, and with Wintie a non-Catholic. She worried it would never come through, but a helpful monsignor said he would take her to the Cardinal Vicar: “Remember, my child, that we are in Rome, where many things arrange themselves.” The Cardinal Vicar weighed Wintie’s good looks and Daisy’s good-faith assurance to raise the children as Catholics and approved the dispensation.

In the Gilded Age, Henry James remarked that even “the waves at Newport chinked silver.” But Winthrop Chanler’s inheritance left him ambitious only for adventure. In Newport, Wintie and Daisy grew weary of dull Astor and Vanderbilt dinners. A more colorful summer seaside companion was the artist John La Farge, who would wander at dawn among the enormous cliff “cottages” in his purple kimono and straw sandals. Theodore Roosevelt, the godfather to their son (also named Theodore), rocked his chair on their porch and recounted the latest adventures of the Boone and Crockett Club. Conversations with Roosevelt always gave Wintie the itch to travel. One week he would be hunting mouflon in Sardinia, the next in Ireland hunting foxes, and soon setting off to search for oil in Morocco. He followed Roosevelt to Cuba with the Rough Riders, escaping with a minor wound. Wherever he went, he and Daisy kept a lively correspondence. He always returned to home base with Daisy and the family before setting off again. Their reunions were frequent and tender, producing eight children. He died twenty-six years ahead of Daisy after collapsing in the saddle during their morning ride together at their Sweet Briar Farm in upstate New York.

Daisy’s friend Robert Speaight, an actor who played Becket in the Broadway premiere of Murder in the Cathedral, treasured her as “an artist of the private life.” Friendship with the Chanlers provided a relaxing private retreat for men in the public life like Roosevelt. During lunch at Henry Adams’s house in Washington, D.C., Henry James asked her to accompany him to see Augustus Saint-Gaudens’s memorial sculpture for the late Clover Adams. James wrote Edith Wharton that Daisy was an essential emotional support for him after Clover’s suicide.

Henry Adams was fascinated by Chanler’s conversion, and they shared a love of medieval sacred music. He relished the lessons she brought back from her visits with Justine Ward to Solesmes, the French abbey where Dom Mocquereau led a twentieth-century revival of Gregorian chant. Adams gave her the only copy of his privately printed “Prayer to the Virgin of Chartres” that he shared while he was alive. If he made a final definite act of faith, his friendship with Daisy prepared him to complete the religious journey he began on the road from Mont St Michel to Chartres:

For centuries I brought you all my cares,
And vexed you with the murmurs of a child;
You heard the tedious burden of my prayers;
You could not grant them, but at least you smiled.

Daisy was, according to Speaight, “a natural patrician in a country where aristocracy enjoys no rights and where no obligations are expected of it.” For this high-born woman of high culture, all history, art, poetry, and philosophy only confirmed the obligation in the penny catechism. She writes in Beyond the Road to Rome: “God made man to know Him, to love Him, to serve Him, that He gave us freedom of soul to obey Him, whom to serve is perfect freedom.”