The Summer John F Kennedy Went On a Grand Tour of Europe With Lem Billings
- Jan 4
- 7 min read
On 30th June 1937, John F “Jack” Kennedy boarded the S.S. Washington with his closest friend Kirk LeMoyne “Lem” Billings and a plan that was deliberately loose. They would cross the Atlantic, pick up Jack’s car, and drive their way through Europe for as long as money, energy, and curiosity allowed. They were not travelling as future statesmen or historical figures. They were two young Americans in their early twenties, slightly overconfident, observant, and very fond of writing things down.
What makes this journey so compelling is not just where they went, but how they recorded it. Both men kept diaries. Jack’s entries are analytical and self assured, full of broad impressions about politics and national character. Lem’s are more conversational, often funny, and rich with small details. Read together, they feel like two voices talking over the same experiences from different angles. One is trying to make sense of Europe. The other is trying to make sure the trip holds together.
They would be away for nearly two and a half months, returning home on 16th September 1937. By then, both were exhausted, slightly unwell, and quietly aware that they had seen something important, even if they could not yet name it.
A Ship Full of Familiar Faces
The crossing itself set the tone. The S.S. Washington was crowded with American students and holidaymakers, and Jack and Lem quickly realised they were surrounded by people from overlapping worlds. Lem noted “Johnny Harvards” on board, along with at least one familiar face from Choate. It felt less like leaving home than carrying a piece of it across the Atlantic.
That familiarity mattered. This was not a lonely or solemn voyage. It was social, chatty, and filled with conversations that drifted from books to politics to plans for the summer ahead. When they arrived at Le Havre on 7th July 1937, Lem’s attention went straight to the practical problem waiting for them.
“We arrived in Harve July 7th and after watching all of the fenders of Jack’s car get scratched we started on our trip.”
Jack’s car, shipped over from the United States, became a central feature of the journey. It gave them freedom to roam, but it also tested their patience. In Lem’s diary especially, the car appears again and again, spluttering, scraping, and generally making itself known.
Paris: Big Ideas and Small Economies
By the time they reached Paris, Jack was already doing what he did best. He was listening, questioning, and forming opinions. On 9th July 1937, he wrote one of the clearest early examples of his political thinking.
“The general impression seems that while they really like Roosevelt, his type of government would not succeed in a country like France which seems to lack the ability of seeing a problem as a whole.”
He went on to note that many people believed there would not be a war anytime soon, and that France felt well prepared for Germany. From today’s perspective, the confidence is striking. At the time, it was common.
Lem’s Paris entry the following day is lighter and far more grounded.
“We are very careful to leave the car around the block and then apply for rooms looking as poverty stricken as possible.”
It is a wonderfully ordinary detail. Two young men trying not to look too comfortable so they could get cheaper rooms. It also hints at something deeper. They were already aware of how appearances shaped treatment. Even on holiday, they were managing perception.
Castles, Rivers, and a First Taste of France
From Paris, they moved into the Loire Valley, stopping at places that felt timeless. Lem’s entry from 19th July 1937, covering Amboise, Chenonceau, and Angoulême, lingers on Chambord.
“It is really an amazingly impenetrable fort. The walls are tremendously high and even today with modern warfare an army would have trouble taking it.”
There is an unspoken awareness here that Europe’s past was never really past. Lem was looking at stone walls built for old wars while thinking about new ones.
This was also the point at which Lem swam in the Loire at Chenonceau and promptly caught a cold. It sounds trivial, but it followed him for weeks and contributed to the sense of weariness that crept into the later stages of the trip. These were long days, long drives, and hot weather, with little time for rest.
Films, Laughter, and the Basque Borderlands
By late July they were in St Jean de Luz, near the Spanish border. Politics was harder to ignore here. Lem noted on 24th July 1937:
“St. Jean de Luz is very definitely a Franco stronghold and we are getting completely the Franco point of view.”
Spain was still in the grip of civil war, and opinions were strong. Yet even here, humour found a way in. Jack wrote on 23rd July:
“Gary Cooper speaking French as well as the Indians is worth the price of admission.”
A few days later, Lem added:
“We went to a movie in French and were plenty amused to hear Pat O’Brien spouting French.”
You can picture them sitting in a darkened cinema, half following the plot, half enjoying the absurdity of familiar voices in unfamiliar languages.
A bullfight on 26th July struck a very different note for Lem.
“Extremely interesting, but terribly cruel… It is not hard to believe the stories about the atrocities in Spain, after seeing a bullfight.”
The language reflects its time, but the reaction is genuine. This was not entertainment that could be shrugged off. It forced them to confront violence as spectacle, and the discomfort stayed with Lem long enough to make it into his diary.
On 29th July 1937, they stopped at Carcassonne. Lem was fascinated by the fact that the medieval town was not preserved as a monument, but lived in.
“People still live inside the walls on crowded little streets, and even they and their horses look medieval.”
It is an observation that captures something essential about the trip. Europe was not just ruins and museums. It was continuity. Past and present overlapping in ways that felt increasingly significant as they moved into countries where the future was being reshaped by force.
The Riviera and a Bit of Beach Theatre
The south of France brought heat, glamour, and a brief emotional dip. On 31st July 1937, Lem wrote from Cannes and Monte Carlo:
“Awoke very late, but very unhappy. Kennedy did a dying act on the beach as shown in the photograph.”
There is a photograph to go with this, Jack sprawled dramatically on the sand. It is playful and slightly ridiculous, and it reminds you that this trip was also full of private jokes and shared silliness. Even as they absorbed heavy ideas, they were still young enough to enjoy the absurd.
Mussolini’s Italy in Paint and Posters
Italy made its politics unavoidable. Lem noted on 2nd August 1937:
“Pictures of Mussolini everywhere, even painted on the walls of houses. All along the roads he has painted his commands, which seem to consist mostly of ‘obey’.”
That single word captures the atmosphere better than a paragraph of analysis. Fascism here was visual and repetitive, pressed into daily life.
A few days later, on 4th August, Lem recorded meeting a German boy named Martin on the road to Pisa.
“Very interesting as he was definitely anti Hitler although he couldn’t tell us much about it.”
Even opposition, it seemed, had to be quiet.
Jack, meanwhile, was actively seeking out political insight. On 10th August 1937 in Rome, he met a journalist and noted down what he heard.
“He said Fascism wasn’t that unfair to the worker… said chief danger of a war was that someone would call Italy’s or Germany’s bluff.”
It is an unsettling entry now, but at the time it reflected conversations happening across Europe. Authoritarian systems were being explained, justified, and normalised in real time.
Germany and the Pull of Propaganda
By mid August they were in Munich, and Lem wrote one of the most revealing lines of the entire trip.
“You can’t help but like a dictator when you are in his own country… Hitler’s strongest weapon seems to be his very efficient propaganda.”
This was not praise. It was an observation about atmosphere. Order, confidence, and repetition can be persuasive, especially to visitors who are only shown what the regime wants them to see.
Around this time, Lem photographed Jack juggling, captioning the image “Jugglin’ Jack”. It is a small but telling contrast. Even in Germany, with propaganda everywhere, Jack was still clowning for the camera.
The Netherlands and the Dachshund That Got Away
One of the most unexpectedly touching episodes of the trip unfolded in Germany and the Netherlands, centred on a dachshund intended as a gift for Olive Hawley, a family friend in London.
Jack wrote on 19th August 1937:
“Bought Offie, a dachshund of great beauty for $8.00 as a present for Olive.”
Lem’s account, written the next day, turns it into a mini saga.
“We have been trying for some time to get a dachshund for Olive… went on many a wild goose chase… finally bought one… we named ‘Dunker’ after the only German word we knew.”
They were attached almost immediately. But logistics, allergies, and practicality intervened. On 24th August 1937, in The Hague, they made a reluctant decision.
“We decided to sell Dunker and parted with him very unwillingly, after taking many last shot pictures.”
It is a small story, but it says a great deal. Amid discussions of war and ideology, they were also two young men quietly sad about giving up a dog.
England, Illness, and the Long Way Home
By late August, the trip was winding down. Lem noted the frustrations of border crossings and customs on 26th August as they travelled from Calais to London. Everything felt slower, heavier.
Lem’s cold lingered, and Jack developed his own problems in Southampton on 27th August after saying goodbye to his mother and siblings.
“Kennedy mixed tomato juice and plenty of chocolate… by the time we reached London he was covered with hives.”
They sailed from Southampton on 10th September 1937 and arrived back in the United States on 16th September. Lem’s final entry is quietly emotional.
“So at last I’m back to the U.S.A after a wonderful trip. I’m sorry as the devil it’s over.”
Why This Trip Still Feels So Close
What makes the 1937 Europe trip endure is not hindsight, but intimacy. These diaries capture Kennedy before his public voice hardened, and Billings as the steady presence who saw everything up close. Paris shows ideas forming. Italy and Germany show persuasion at work. The Netherlands shows tenderness and regret. France offers laughter, fatigue, and history underfoot.
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