As early as August 1517, a clause of the Treaty of Rouen provided that if the Auld Alliance between France and Scotland was maintained, James should have a French royal bride. Yet the daughters of Francis I of France were promised elsewhere or sickly.[18] Perhaps to remind Francis of his obligations, James's envoys began negotiations for his marriage elsewhere from the summer of 1529, both to Catherine de'Medici, the Duchess of Urbino, and Mary of Austria, Queen of Hungary, the sister of Holy Roman Emperor Charles V. But plans changed. In February 1533, two French ambassadors, Guillaume du Bellay, sieur de Langes, and Etienne de Laigue, sieur de Beauvais, who had just been in Scotland, told the Venetian ambassador in London that James was thinking of marrying Christina of Denmark.[19]
Francis I insisted that his daughter Madeleine's health was too poor for marriage. Eventually, on 6 March 1536, a contract was made for James V to marry Mary of Bourbon, daughter of the Duke of Vendôme. She would have a dowry as if she were a French Princess. James decided to visit France in person. He sailed from Kirkcaldy on 1 September 1536, with the Earl of Argyll, the Earl of Rothes, Lord Fleming, David Beaton, the Prior of Pittenweem, the Laird of Drumlanrig and 500 others, using the Mary Willoughby as his flagship.[20] First he visited Mary of Bourbon at St. Quentin in Picardy, but then went south to meet King Francis I.[21] During his stay in France, in October 1536, James went boar-hunting at Loches with Francis, his son the Dauphin, the King of Navarre and Ippolito II d'Este.[22]
James renewed the Auld Alliance and fulfilled the 1517 Treaty of Rouen on 1 January 1537 by marrying Madeleine of Valois, the king's daughter, in Notre Dame de Paris. The wedding was a great event: Francis I made a contract with six painters for the splendid decorations, and there were days of jousting at the Louvre.[23] At his entry to Paris, James wore a coat described as "sad cramasy velvet slashed all over with gold cut out on plain cloth of gold fringed with gold and all cut out, knit with horns and lined with red taffeta."[24] James V so liked red clothing that, during the wedding festivities, he upset the city dignitaries who had sole right to wear that colour in processions. They noted he could not speak a word of French.[25] When James was at Compiègne on 25 February 1537, a messenger from Pope Paul III arrived with a gift of a sword and hat.[26]
James and Madeleine returned from France on 19 May 1537, arriving at Leith, the king's Scottish fleet accompanied with ten great French ships.[27] As the couple sailed northwards, some Englishmen had come aboard off Bridlington and Scarborough. While the fleet was off Bamburgh on 15 May, three English fishing boats supplied fish, and the King's butcher landed in Northumbria to buy meat.[28] The English border authorities were dismayed by this activity.[29]
Madeleine did not enjoy good health. In fact, she was consumptive and died soon after arrival in Scotland in July 1537. Spies told Thomas Clifford, the Captain of Berwick, that James omitted "all manner of pastime and pleasure," but continually oversaw the maintenance of his guns, going twice a week secretly to Dunbar Castle with six companions.[30] James then proceeded to marry Mary of Guise, daughter of Claude, Duke of Guise, and widow of Louis of Orleans, Duke of Longueville, by proxy on 12 June 1538. Mary already had two sons from her first marriage, and the union produced two sons. However, both died in April 1541, just eight days after baby Robert was baptised. Their daughter and James's only surviving legitimate child, Mary, was born in 1542 at Linlithgow Palace.