I Traced the Steps of Hemingway, Picasso, and Chanel Through France and Spain—Here’s What I Discovered
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On a summer afternoon in Biarritz the temperature hovers at 97 degrees, but beneath the shade of tamarisk trees and a breeze off the Atlantic Ocean, it’s manageable. Pleasant even. A local artist named Juliette has arranged a palette, tubes of acrylic paint, and brushes on a park bench that faces the same coastline Pablo Picasso painted in 1918 while honeymooning with Olga Khokhlova. Scanning the horizon line, I spot the 19th-century lighthouse he put to canvas in The Bathers. Juliette instructs me to close my eyes and focus on each sense individually—and to maintain that heightened state once my eyes are open. “That’s what painting should feel like,” she says. A bit esoteric, but nevertheless an effective prompt. My subsequent brushstrokes of Biarritz are predictably subpar (Picasso, I am not), but who cares? I am in France and my senses are heightened!
I’ve come to Europe in search of The Lost Generation. Or rather, to trace their steps. This year marks the centennial of Ernest Hemingway’s The Sun Also Rises, the 1926 novel that evinced the disillusionment of the expatriate era following The Great War; a period that was also marked by stratospheric creativity. Seeing as I foster similar feelings of disillusionment, and always a deep yearning for nostalgia, when I learned Black Tomato had crafted a travel itinerary around the places and personalities that defined this era, I was on a transatlantic flight faster than you could say une generation perdue.
In the days that followed my arrival, I would be transported to the historic cafés of Montparnasse, to San Sebastián’s cobblestone alleys for pintxos and Basque cider, and to the world’s oldest restaurant in Madrid, where Hemingway’s favorite booth remains in the back corner like a bacchanalian shrine. I would sleep in Grand Dame hotels—each one frequented by the Lost Generation crowd—and I’d round it out with exploration of bookshops, cycling paths, museums, and watering holes. (Lots of watering holes).
Biarritz
My time in Biarritz is brief but brilliant. After packing up the paintbrushes and bidding au revoir to Juliette, I check into Hôtel du Palais Biarritz. It was originally constructed in 1854 as a summer villa for Napoleon III and Empress Eugénie, but later converted into a hotel. But oh my, does it still resemble an imperial palace. From the regal wrought iron entrance to the marble columned lobby decorated with antique clocks and chandeliers, it’s sumptuous through and through.
The hotel sits at the Atlantic’s edge, and my room overlooks the lighthouse that I (and Picasso) painted. I imagine what it must have been like when Coco Chanel—a regular guest—stayed here while opening her first couture house up the road at the Villa de Larrald in 1915. Little did she know over a century later Matthieu Blazy would hold a runway show at the town’s Casino Municipal.
After a casual dinner in the Les Halles neighborhood, I kick off my sandals and take a sunset stroll along the Grande Plage. The day might be winding down but everyone is still in the water. Dogs, children, lovers. The air is thick and warm and salty and I let my imagination float to the 1920s, picturing striped changing tents on the sand and ladies with spinning parasols. La Côte Basque has intoxicated my senses, as it has all others before me.
Paris
As Gertrude Stein once declared, “Paris was where the 20th century was.” In the aftermath of World War I, writers and painters flocked here in pursuit of artistic liberation, bucking Victorian traditions and shaping culture for every generation that followed. My sojourn in Paris begins at Hôtel de Crillon, A Rosewood Hotel (the grandest of grand dames). Stepping past its neoclassical façade, the summer heat and hum of traffic encircling Place de la Concorde soften as cherubed frescoes offer an opulent greeting.
During the 1920s, the Crillon’s reputation was equally prestigious. “At five o’clock I was in the Hotel Crillon waiting for Brett,” Hemingway wrote in The Sun Also Rises. “She was not there, so I sat down and wrote some letters. They were not very good letters but I hoped their being on Crillon stationery would help them.” I follow his cue and take a few sheets of stationery for my journey.
That afternoon I take advantage of my proximity to Bar Hemingway over at the Ritz Paris. As the story goes, in 1944 the writer showed up at the Place Vendôme in a Jeep mounted with a machine gun to “liberate” the hotel and its bar from the German occupation. The Nazis had already cleared out by that point, but Hemingway still managed to run up a tab for 51 martinis. (Despite the shenanigans, The Ritz named the bar after him in 1994.) I order a martini in his honor, which arrives with a white rose on the rim, as is customary for cocktails delivered to women at Bar Hemingway. Next, I head across the Pont Royal en route to one of my favorite restaurants, Brasserie Lipp, an old haunt for Lost Generation figures that first opened in 1880. Seated beneath the Art Nouveau murals by Léon Fargues, I order the house beer (grande), escargots, herring filets with pommes à l’huile, and knife-cut sausage from Maison Brosse. As “Papa” Hemingway would likely have said, it was all damned good.
Black Tomato arranges a private tour of Montparnasse with a local guide named Maude. We begin the following day at La Coupole with un café et un croissant, studying the brasserie’s painted columns that date to its opening in 1927. Downstairs there is an Art Deco dance hall that was once the site of extravagant artist parties (Josephine Baker was a regular).
Next, we walk to Café du Dôme. Photographs of patrons from the restaurant’s bohemian past line the red velvet banquettes, from Modigliani to Man Ray. Next, Le Select, with its bistro tiled floors and zinc bar. Upon exiting, I spot an elderly man sitting alone with a sketchpad. The whole scene is awfully romantic. Our final brasserie is La Closerie des Lilas, where Hemingway clocked countless hours writing, and where small plaques are screwed onto tabletops once preferred by famous patrons. Maude points to one of these. I look closer: “F. Scott Fitzgerald.”
Spend enough time milling about Montparnasse and you’ll bump into plenty more history: Modigliani’s house that he shared with wife Jeanne Hébuterne before dying of tuberculosis, Sylvia Beach’s home at 12 Rue de l’Odéon (also the site of the original Shakespeare & Company), and Gertrude Stein’s legendary residence and salon at 27 Rue de Fleurus.
Before wrapping up the day, we pivot to Place Vendôme for a spritz of Chanel. (Did you know the Vendôme’s geometric layout inspired the shape of the N°5 perfume bottle?) Five minutes up the road is Angelina, the Belle Epoque pâtisserie and tea salon where Chanel and Jean Cocteau would often come to enjoy a Mont Blanc dessert. On my return to the Crillon, we pass 31 Rue Cambon, the mothership, where Chanel’s personal residence, boutique, and couture atelier lie.
I eke out as much romance as I can from my dwindling Parisian hours: a steam and swim at the Crillon’s glamorous subterranean spa, a whisky cocktail at Bar Les Ambassadeurs, oysters and dry-cured ham at Nonos & Comestibles, and a balmy late-night stroll along the Seine. “Paris was always worth it,” Hemingway wrote in A Moveable Feast, “and you received return for whatever you brought to it.” Regardless of the circumstance—a historic heatwave in my case—Paris has never failed to ignite an appreciation of simply being alive.
San Sebastián
I’m welcomed to San Sebastián by a galerna, a sudden and violent storm typical to Spain’s Basque Coast. It offers a theatrical excuse to hole up in the Hotel Maria Cristina with a bottle of txakoli and a plate of gildas (a popular pintxo, or bar snack, consisting of a green olive, guindilla pepper, and anchovy on a toothpick). The coastal enclave is just an hour from Pamplona, where the running of the bulls in The Sun Also Rises takes place. It is also where the protagonist, Jake, recovers after the festival with ocean swims and quiet meals. Black Tomato determines the best way to channel the Lost Generation in San Sebastián is by eating and drinking with locals, and I gleefully oblige.
The next morning, my guide Jani walks me through a food market in the old city. “We are very loyal to our vendors,” she says, passing a stand stocked with guindilla peppers. We are gathering provisions to cook a meal in one of San Sebastián’s gastronomic societies—private, members-only social clubs that originated in the mid-19th century. The loophole to gaining entry? Having a member invite you in. Our gracious member, Cristina, arrives at the market as we continue to shop for Hake fish, txistorra, anchovies, and smoked cheese.
There are around 100 clubs in town, and many are themed after a hobby. Cristina’s—founded in the 1950s—is hipica (equestrian). We descend down a flight of stairs and arrive at a small room with wood paneling and an impressive kitchen. What comes next is a fever dream of Basque flavors: anchovies prepared three different ways, shrimps in whisky sauce, hake with potatoes covered in garlic, olive, and parsley—and plenty of cider and txakoli to wash it down.
“Gutxi eta maiz,” Cristina says to me as she pours the wine high above the glass, creating a light fizz. It translates to “little and often”—the way Basques enjoy their drink. This is echoed in The Sun Also Rises. “…he held the wine-bottle at full arms’ length and raised it high up,” Hemingway wrote, “squeezing the leather bag with his hand so the stream of wine hissed into his mouth.” After a few tries, I nearly get the hang of it.
I set out for a pintxos tour the following day with Vero, another local guide. Pintxos didn’t exist when Hemingway attended his first San Fermín festival in Pamplona. What did, Vero explains, was the same convivial spirit that led to his fascination with Basque culture. We sample a scallop with caramelized leeks emulsified in an ajo blanco soup (wow), foie gras with white chocolate and salted corn (double wow), toss back a few oxtail croquettes, and finish with torrija, a thick block of brioche that’s been soaked in a milk bath.
Madrid
My final leg is Madrid, and only The Palace will do. The Luxury Collection hotel originally opened in 1912 by King Alfonso XIII, and also appears at the end of The Sun Also Rises. The hotel is located in the Golden Triangle of Art and is a quick walk from the Prado and Reina Sofia museums. I’m privately escorted throughout both, stopping at highlights like The Garden of Earthly Delights (a precursor for Dalí’s signature surrealism), Goya’s haunting Black Paintings (do not look up Saturn Devouring His Son), and Picasso’s anti-war masterpiece, Guernica. My guide María also takes me to the couture atelier of Santiago Bandrés, where the designer—who trained at Cátedra Balenciaga—pulls out intricately embroidered shawls and silk gowns from his archives. María (who is also a seasoned flamenco dancer) does a finger snap and spins around the room in one of them.
Lunch is served at Sobrino de Botín, the oldest restaurant in the world. It’s famous for roast suckling pig, which has been the signature dish since opening in 1725. Hemingway first dined here during his summer in Madrid in 1923, later immortalizing the landmark (and the pig) in his novel, and continuing to visit for decades to come. Owner José “Pepe” González tells me that despite the literary connection, they never hang photos of famous customers; it’s just not their bag. “We host people how we would want to be hosted,” González says. (If you ask nicely, though, the staff might show you Hemingway’s favorite corner table upstairs.) González shares it’s his last day before retirement, and I ask what that means for the future of Botín. He isn’t worried. “People don’t come here because I’m here—they come because of the continuity, the service, and the atmosphere.” A sentiment that seems to thread through all of my stops on this journey thus far.
My remaining time is limited, but there are a few excursions that must be squeezed in. First, a glass of sherry at La Venecia, an old Hemingway watering hole during the Spanish Civil War frozen in time with its dusty bottles and barrels (made all the more authentic thanks to the no-photos rule). Next, a browse through a rare bookstore in the Literary Quarter that María recommended, followed by The Palace’s bar. It’s breathtaking—with a chandelier of 1,875 crystals and a stained glass ceiling that lets so much light in, the space was used as an operating room during the Civil War. “It’s funny what a wonderful gentility you get in the bar of a big hotel,” Brett says in reference to The Palace in The Sun Also Rises. She and Jake sip a martini, so I follow suit. Midway through, the bartender empties my martini into a fresh, frozen glass. Gentility, no question about it.
The trip concludes with a dinner and performance at Tablao Flamenco Corral de la Morería, where photos and videos are forbidden. Dancers Florencia Oz and Jesús Fernández take the stage, rhythmically stomping their feet and clapping their palms together. Two singers, a guitarist, and a cellist join in. Her crimson ruffled dress, his impassioned shouts, the disregard for anything other than that moment in time—the intensity earnestly brings me to tears. I came in search of The Lost Generation, to find traces of a life fueled by the pursuit of artistic enlightenment. What I found proved much better. A simple need to be in the world, to be among strangers, to be human.







