The Sun Also Rises turns 100 this year, making it the right time to visit the cafés, coastlines, and wine cellars that fill its pages. When you create a bespoke itinerary with Black Tomato, you can choose to lean into Hemingway's literary haunts, Picasso's studios, or Chanel's ateliers, or take all three in equal measure.
Paris, Days 1-3
Hemingway wrote most of The Sun Also Rises at La Closerie des Lilas on Boulevard du Montparnasse, the same table where he first read Fitzgerald's manuscript of The Great Gatsby. A scholar of 1920s Paris leads the Left Bank walk through Place de la Contrescarpe and Rue Mouffetard before finishing with a picnic in the Luxembourg Gardens. Day two goes inside the Musée Picasso with a private guide, followed by a cocktail masterclass featuring Hemingway's frozen-onion martini. Day three traces Chanel's story from the Ritz to Rue Cambon. Home base is Relais Christine, built into a centuries-old Augustinian abbey.
Biarritz, Days 4-5
Chanel opened her first couture house here in 1915. Picasso honeymooned here three years later with Russian ballerina Olga Khokhlova, painting The Bathers on the seafront, the first canvas in a series he'd return to for decades. A private neighborhood walk and sundowners with a former stylist are followed by a plein air watercolor class in the same coastal light Picasso worked by. Home base is the Hôtel du Palais, built by Napoleon III for Empress Eugénie in 1855.
San Sebastián, Days 6-7
Hemingway was a regular, sometimes immovable, fixture at the city's bars. A specialist guide leads a literary promenade through narrow streets, txakoli poured into waiting glasses along the way. Day seven opens the doors of a private txoko, one of the Basque gastronomic societies that rarely admits outsiders, for a dinner prepared with a local chef. Home base is the Hotel Maria Cristina, a Belle Époque landmark that Chanel chose as the backdrop for her post-war fashion shows.
Rioja, Days 8-9
A stop at the Cristóbal Balenciaga Museoa in Getaria before heading into wine country. In Haro, the cellars of Bodegas Franco Españolas open for a private visit, the proprietors pairing vintages with stories of Hemingway passed down through generations. Rioja Alta appears by name in The Sun Also Rises. Picasso left Spain in 1934 and never came back. Hemingway kept returning until the end, and the wine was a large part of why.
Madrid, Days 10-12
Home base is The Palace, the grand early 20th-century hotel where Jake Barnes drinks at the bar in The Sun Also Rises. A private guide through the Prado traces the masterpieces that shaped Picasso from Velázquez to Goya, followed by lunch at Sobrino de Botín, the world's oldest continuously operating restaurant, founded in 1725, where Goya once worked in the kitchen. The final day ends at the Reina Sofía, standing in front of Guernica, the painting Picasso made in grief and fury after a single afternoon of bombing erased the Basque town that gave it its name in 1937.
Presented by Black Tomato.
