(in case you're wondering, this is a parody website, but the Latin is serious)
The Professor has written briefly comparing the travels of Caesar and Churchill. He has created two map quizzes as well:
Caesar and Churchill’s Parallel Journeys
Turkey
Churchill
1910 He visits Ephesus. Winston had a seat secured right at the front of the locomotive, above the cow catcher. The best way to see the countryside, he said.
1943 Winston took a detour from the Casablanca conference to try and persuade the Turks to join the war.
1959 Winston is a guest on the yacht of Aristotle Onassis when it drops anchor in Izmir. Onassis had fled Izmir as a child in 1922.
Julius
80-81 BC Served in army in Turkey. Awarded Civic Crown for bravery during the siege of Mytilene, Lesbos.
75 BC Captured by pirates on route to Rhodes; probably held in coastal Turkey; scorns them for not appreciating his poetry; later executed them.
74 BC gathered his own army and took part in Mithridatic War III.
47 BC defeats Pharnaces II of Pontus at Battle of Zela (modern day Zile); announces ‘veni vidi vici
Egypt
Churchill
1898 Took a steam boat up the Nile to join Kitchener in his mission to defeat the Mahdi.
He returned for a vacation in 1899.
Sees the Aswam dam opened in 1902.
1940-44 Winston makes several trips to Egypt to inspect the army and to conduct foreign policy. It was an obvious stopping off place on the way to visit Stalin in Moscow and Tehran.
Caesar
48-47 BC Caesar pursuing Pompey to Egypt finds him murdered; siege of Alexandra; takes Cleopatra up the Nile.
Africa West of Egypt
Churchill
Winston reviewed the victorious 8th Army in Tripoli.
1935 He visited Marrakesh for the first time.
He took Roosevelt there after the Casablanca conference. Sipping drinks on the terrace, they watched the snows of the Atlas mountains reflect the setting sun. ‘The most lovely spot in the world,’ he is reported to have said. The next day he painted the only picture he painted during the war- a view of the mountains.
Winston returned to Morocco on three occasions after the war, staying at the Mahmounia Hotel.
Caesar
46 BC Caesar falls flat on his face getting off a boat; turns it into a good omen by declaring he has embraced Africa; defeats Pompey loyalists under Metellus Scipio at battle of Thapsus.
Greece
Churchill
Winter 1944-45 Winston visited to negotiate between different resistance groups. Unless you believe the Guardian, https://www.theguardian.com/world/2014/nov/30/athens-1944-britains-dirty-secret. But don’t.
Caesar
Caesar could have used a combination of land and sea travel to get to Rhodes or Lesbos (see Turkey, above) so it’s probable he stopped off in Greece on the way.
48 BC Caesar overplays his card in battle of Dyrrhacium and has to withdraw; at battle of Pharsalus he gains a decisive victory over Pompey.
Spain
Winston
1905 Winston travelled through Spain by train on his way to Morocco. I have found no records of his actually stopping off in a Spanish Town.
During WWII Winston stopped off in Gibraltar frequently. Gibraltar was crucial to the Allies.
Julius
69 BC Caesar serves in administration in Spain. He visits Cadiz and seeing a statue of Alexander the Great he wept. When asked why, he said ‘Do you think I have not just cause to weep, when I consider that Alexander at my age had conquered so many nations, and I have all this time done nothing that is memorable?’
60-61 BC Caesar was governor of Spain; 60 BC wins victories over Calaici and Lusitani
49 BC defeats Pompeian army at battle of Ilerda.
46 BC Caesar has to return to Spain to win his final battle over the Pompeians at Munda.