An attempt at a chronology of the life of Charles V:

24 February 1500 - Born in Ghent
November 1501 - his parents leave for Spain
late 1504 - His parents return from Spain
April 1506 - His parents leave for Castile again, where Philip is crowned king.
September 1506 - his father dies in Castile; Charles's grandfather Ferdinand takes the regency of Castile for his daughter; Charles inherits the Netherlands and Burgundy under the regency of his aunt Margaret; Charles mostly grows up in Malines.
1515 - declared of age in the Netherlands. Chièvres becomes his favorite minister.
23 January 1516 - death of Charles's grandfather Ferdinand; Ferdinand leaves Aragon to his daughter Juana (Charles's mother); Cardinal Jimenez is regent of Castile; the Archbishop of Saragossa in Aragon
early 1516 - Charles proclaimed king of Spain in Brussels; he appoints his tutor Adrian of Utrecht as governor of Castile, but this is ignored. Shortly thereafter Jimenez has him proclaimed in Castile.
August 1516 - Treaty of Noyon is signed with France, ending their war in Italy.
8 September 1517 - Charles sets sail from Flushing.
October 1517 - meets the constable of Castile, meets his mother at Tordesillas, learns of Jimenez's death.
18 November 1517 - Charles enters Valladolid, the Castilian capital
2 February 1518 - Meeting of the Cortes of Castile; Cortes takes oath of allegiance to Charles
later in 1518 - secures the allegiance of Aragon
1519 - travels to Barcelona, learns of the death of paternal grandfather, Emperor Maximilian I; Charles acknowledged by the estates of Catalonia
28 June 1519 - Charles elected Emperor at Frankfurt, in absentia
Late 1519 - Charles travels back across Spain towards Galicia, travelling via Burgos and Valladolid.
30 March 1520 - Charles opens the session of the Cortes at Santiago de Compostela; stays on until 4 April
22 April 1520 - Cortes reopens at Corunna where Charles will re-embark for the Netherlands; Adrian of Utrecht appointed viceroy of Castile.
26 May 1520 - Charles lands at Dover and meets Wolsey.
27 May 1520 - Charles travels to Canterbury, meets King Henry VIII and Queen Catherine
July 1520 - Charles meets Henry VIII again at Calais
September 1520 - in the Netherlands, where he issues a decree against Lutheranism
23 October 1520 - crowned king of the Romans at Aachen
January - 26 May 1521 - at the Diet of Worms
16 April 1521 - First Meeting with Luther at Worms
28 May 1521 - Death of Chièvres, Charles's chief advisor
June 1521 - Charles returns to the Netherlands
August 1521 - Charles meets Wolsey at Bruges
26 May 1522 - Departs Calais for England, visits Henry VIII for six weeks (at Greenwich)
6 July 1522 - Charles sails from England for Santander, Spain
1522 - Santander to Valladolid, where he deals with the aftermath of the Comunero Rebellion.
February or March 1525 - Charles is at Madrid when he learns of his army's great victory over Francis at Pavia.
18 September 1525 - Hunting in the Segovia Forest, Charles learns that the captive Francis I is dying in Madrid, and returns to meet him.
13 January 1526 - signs Treaty of Madrid with the captive Francis I
March 1526 - marries Isabella of Portugal at Seville. Charles proceeds to visit Cordoba and Granada, where he is in June.
21 May 1527 - The Emperor's son Philip, Prince of Asturias, born at Valladolid. Here the Emperor learns of the sack of Rome by his mutinous troops.
January 1528 - Charles receives France's renewed declaration of War, somewhere in Spain.
29 June 1529 - Treaty of Barcelona between Clement VII and the Emperor; Charles V perhaps here personally?
12 August 1529 - Having sailed from Spain, Charles arrives at Genoa; soon after he ratifies the Treaty of Cambrai at Piacenza.
5 November 1529 - Travelling via Parma, Modena, and Reggio, Charles arrives at Bologna.
24 February 1530 - Charles crowned Emperor by Clement VII at Bologna
April-May 1530 - Charles crosses the Brenner Pass into Germany. He visits Innsbruck.
25 June 1530 - at the Diet of Augsburg
5 January 1531 - apparently present at the election of his brother as King of the Romans, presumably in Frankfurt
1532 - Diets at Nuremberg, then at Regensburg; not sure if Charles was personally present
June 1532 - leads an expedition against the Turks from Vienna
1533 - Returns to Spain via Italy; arrives in Spain in April.
30 May 1535 - departs Barcelona headed for Tunis.
16 June 1535 - Charles's forces debark at Carthage and besiege La Goulette
4 July 1535 - Charles raises the siege of La Goulette, heads for Tunis
14 July 1535 - Tunis besieged
21 July 1535 - Tunis captured; Charles heads to Sicily - going from Trapani to Palermo to Taormina to Messina
3 November 1535 - Charles crosses the Straits of Messina to the Kingdom of Naples
5 April 1536 - Visits Rome, meets with Pope Paul III, challenges Francis I to personal combat; travels on to Siena, Florence, Lucca, Pontremoli, Borgo San Donnino, and Asti.
Summer 1536 - Charles invades Provence via Nice and Aix, where he is on 14 September; soon after returns to Genoa
November 1536 - Charles sails for Spain, after a storm, lands safely at Palamos
31 January 1538 - Charles, at Barcelona, writes to the people of Ghent.
18 June 1538 - Signs truce of Nice with Francis I; soon after Charles visits Francis at Aigues-Mortes and they are reconciled. Soon after, Charles returns to Spain.
1 May 1539 - Empress Isabella dies at Toledo
12 December 1539 - Enters France on his way to the Low Countries, met at Loche by King Francis and Queen Eleanor
1 January 1540 - Enters Paris
21 January 1540 - meets his sister Mary at Valenciennes, travels on to Brussels
9 February 1540 - leaves Brussels for Ghent.
14 February 1540 - Charles enters Ghent.
29 April 1540 - Charles passes judgment on rebellious Ghent.
January 1541 - Charles heads to Germany.
Spring 1541 - at Diet of Regensburg
Summer 1541 - crosses the Brenner Pass to Italy; meets Cosimo de' Medici and Pierluigi Farnese at Genoa, and the Pope at Lucca.
September 1541 - Sails from La Spezia to Majorca, then leads attack on Algiers
23 October 1541 - Landing near Algiers
November 1541 - Charles abandons attack on Algiers, returns to Spain
1543 - Leaves Spain, sails to Genoa, visits Piacenza and Cremona, travels via Brenner pass to Germany
later 1543 - Charles campaigns in the lower Rhine against the Duke of Cleves.
October 1543 - Charles joins the army investing Landrecy.
February 1544 - at Diet of Speyer
13 July 1544 - Charles joins imperial army besieging Saint Dizier
17 August 1544 - Capitulation of Saint-Dizier; Charles invades France
31 August 1544 - Charles at Chalons
12 September 1544 - Advances to Soissons
18 September 1544 - Signs Treaty of Crépy with France
May-August 1545 - at Diet of Worms. Afterwards, Charles returns to the Netherlands.
Spring-Summer 1546 - Travels from Maastricht via Speyer to the Diet of Regensburg
Summer 1546 - Outbreak of the Schmalkaldic War. Charles marches from Regensburg to Ingolstadt.
31 August - 3 September 1546 - the Schmalkaldic Army bombards Charles in Ingolstadt
September-October 1546 - Charles moves up the Rhine from Ingolstadt towards Ulm, thence eventually to Nördlingen.
Spring 1547 - Charles leaves Nördlingen for Regensburg and Eger
13 April 1547 - Charles crosses the Saxon frontier
23-24 April 1547 - Defeats the Schmalkaldic League at Mühlberg
23 May 1547 - Enters Wittenberg in triumph
19 June 1547 - Philip of Hesse surrenders to Charles (where?)
1548 - Most of year spent in Augsburg, including Diet thereof
1550-1551, another diet at Augsburg
19 April 1552 - the Emperor is surprised at Innsbruck by Maurice of Saxony; flees from Innsbruck (to where?)
19 October 1552 - 1 January 1553 - at unsuccessful siege of Metz
1553 - failed invasion of Picardy
1554 - another invasion of Picardy
25 October 1555 - abdication in Brussels
Late 1556 - returns to Spain, goes to monastery at Yuste
1558 - Dies at Yuste.

Sources are mostly various internet sites, especially Edward Armstrong's 1902 biography, this timeline, the 1911 Britannica article, the current Britannica article, the Catholic Encyclopedia article, various wikipedia articles, including ones on Charles V in English, Italian, French, and German, and also Braudel's The Mediterranean for the later period.