France & Spain

In search of the Lost Generation

Discover the places and personalities that defined an era
france, spain

The Lost Generation

Published 100 years ago this year, Ernest Hemingway’s The Sun Also Rises became the indisputable guidebook to the Lost Generation: that restless confederation of artists, writers, poets and personalities who broke the codes and rewrote the rules of their era.

But their art and their ideas didn’t emerge in a vacuum. They found life in real, vivid living places. They might have been “lost”, but they didn’t need a map to find their way.

This new journey follows the boozy, brooding, beautiful footsteps of Ernest Hemingway, Pablo Picasso, and Coco Chanel, reliving the places, rituals and communities that inspired them – and continue to inspire artists today. This is a living act of time travel, where you'll walk away with a finer feeling for how the world shapes us – and how art can reshape the world.

When

October - April

Price

From $26,000pp excl. flights
Price includes all accommodation, experiences, guiding and transfers. Based on travelling off-peak and may increase if travelling over peak season. Price excludes international flights but these can be arranged on request. See here for more information.
(based on 2 ppl sharing)

How long

12 nights
Ideal length
Days 1-3

Paris

The “city of light” belonged to the Lost Generation. They clung to its bars, bookshops and boltholes with a heady abandon, feeling like it was the center of the world. It was here that Hemingway – in cold rented rooms and cafés – put pen to paper, where Gabrielle Chanel styled and sewed, where Picasso reimagined what painting could look like. The traces of their world are still here, if you know where to find them. You’ll have three days to unravel it. Slowly.

Day 1
“You are an expatriate, see. You hang around cafés.”*

The Left Bank is the natural starting point. Today, a scholar of 1920s Paris – as bohemian as it was chic – will walk you through the places that defined it: Place de la Contrescarpe, where Hemingway crafted his early works. Rue Mouffetard’s lively market stalls. The stacked shelves of legendary bookshops. Later, you’ll arrive at the Luxembourg Gardens for a lavish picnic inspired by the palates of Ernest, Pablo, and Gabrielle.

By night, you’ll slip into soft sheets at Relais Christine – a boutique hotel built into the bones of a centuries-old Augustinian abbey. You’re here for three nights.

 

*keen-eyed readers will note that we’ve titled each of our days with a line from The Sun Also Rises.

Day 2
“How about some of that champagne?”

The Musée Picasso holds the world’s largest collection of the master’s work, and its high halls capture his artistic evolution: from blue to pink to Cubist to Surreal. With a private guide, it becomes something more intimate: where you’ll fill in the brushstrokes around the works and places you’ll be visiting over the coming days.

Later, we’ve organized a private mixology workshop where we’ll recreate the 1920s through the flavors that defined it. Hemingway’s notorious martini – with its frozen onion – takes center stage. It’s history in a glass, even if it’s not to everyone’s taste.

Day 3
“My sort of thing”

Your final morning in Paris belongs to Gabrielle Coco Chanel. A symbol of French elegance, Chanel broke the codes and liberated the bodies of women during Paris’ années folles (“crazy years”). It was sportswear chic, little black dresses, and the audacious No. 5.

You’ll meet your guide at the Ritz for coffee and scene-setting. From here, you’ll retrace the story of Gabrielle through her beloved Right Bank. From Place Vendôme, pausing at Charvet – shirtmaker to Coco, Hemingway and Gertrude Stein – and Chaumet the jewellers. Eventually, you’ll arrive at Rue Cambon – the historic heartland of Chanel.

Days 4-5

Biarritz

Biarritz – that legendary stretch of Basque coastline – is where the Lost Generation summered, loved and kindled their inspiration. Chanel opened her first couture house here in 1915. Picasso honeymooned in 1918, painting in that soft coastal light that illuminates the seafront. The same Belle Époque architecture stands here as it did then, just as the Atlantic still breaks dramatically against the rocks below. Nothing much has changed over a century. But why change perfect?

Day 4
“They were all such nice people”

Today, a specialist guide will lead you on a private walk through the city’s most iconic neighborhoods, including a private, guided visit to the one-time workshops of Maison Germaine. The afternoon’s real pleasure is a rare encounter: spending time with a former stylist and fashion model who played a role in Biarritz’s couture scene. She’ll share personal memories and behind-the-scenes anecdotes over champagne. Tonight, your home is the Hôtel du Palais – the grandest address on the seafront.

Day 5
“Clear and bright and inclined to blur at the edges”

Biarritz’s iconic seafront provides the canvas for a private plein air painting masterclass, where you’ll take inspiration from your journey to create a lasting memento. The coastal light you’ll paint by is the same that drew Picasso here in 1918: responsive, shifting, and specific to the Atlantic’s ragged edge. We’ve designed this class to work for all levels of skill and experience. You’ll leave with something special – made by your own hand.

Days 6-7

San Sebastián

San Sebastián is outrageously elegant. It sweeps, embracing the curve of La Concha Bay. This is the cultural, creative and culinary heart of Basque country that Hemingway would fall head over heels for – becoming a regular (at times immovable) fixture at its bars and restaurants. Picasso, meanwhile, would capture the torment and terror of the war that visited the region, while Chanel – with her eye to a softer beauty – chose the city’s María Cristina hotel as the backdrop for her post-war fashion shows.

Day 6
“I went to lunch”

Making your way to San Sebastián, you’ll stop to wake up with the fishing village of Pasajes. Pastel houses, balconies overflowing with flowers. This is the rugged Basque landscape that Hemingway so romanticized and admired.

Arriving in San Sebastián, you’ll set off on a literary promenade with a specialist Hemingway guide – weaving through narrow streets scented with grilled seafood and oak, waxing lyrical with literary anecdotes. Moving from one iconic bar to the next, txakoli poured into waiting glasses, you’ll become part of a ritual that has endured for generations. Your base for two nights is the Hotel Maria Cristina – long favored by artists, aristocrats, and film stars. It couldn’t be more fitting.

Day 7
“Let us rejoice and give thanks”

The doors of Basque gastronomic societies rarely open to outsiders, where membership is a guarded currency along the coast. They are secret – and proud of it. Tonight, however, we’ll open the doors of a legendary txoko just for you.

Don’t think of it as a restaurant. Think of it as an intimate, free-flowing sanctuary to the salt, fat, acid art of gastronomy. Inside, a local chef will guide you through seasonal ingredients, dishes, drinks and stories. It’s more familial than formal. You’ll see why Hemingway couldn’t get enough of them.

Days 8-9

Rioja

Rioja typifies everything Hemingway loved about Spain: the long lunches, the quiet pleasures, the animated conversation. It is a rustic place. A real place. Rioja – that legendary wine drawn from the bruised-blue grapes of Tempranillo – is the river that flows through everything. It’s what first brought Hemingway here in ‘56 – and it’s what kept him coming back. Picasso – in mourning for his homeland – never once returned after 1934.. For you, Rioja provides a contemplative pause before moving on to your final chapter in Madrid.

Day 8
“Isn't it pretty?"

For Coco Chanel, Balenciaga was “the only couturier in the truest sense of the word”. They might have been contemporaries, but they weren’t rivals. On your way to Rioja, you’ll visit the Cristóbal Balenciaga Museoa – a serene museum and archive overlooking the sea. Here, a dedicated guide will weave the story of Balenciaga and modern fashion. The structure, the emotion, the passion – and how it was fed by the Basque landscape.

From here, you’ll be making your way into wine country – and the lively rhythms of La Rioja.

Day 9
“It's a good place. There's a lot of liquor.”

Here, in Haro, along the banks of the Ebro, you’ll be stepping into a place whose heritage runs deep – and where the best bottles have been passed down through the generations. It runs in the blood. Hemingway – fresh from the corridas of Logroño – visited the cellars of Bodegas Franco Españolas in the hot summer of 1956. He made a regular home here.

Inside, the proprietors will introduce you to the barrels, bottles and vintages that make up their collection – just as they’ll introduce you to stories of Hemingway that have been passed down from parent to child. He knew this place – and he loved this place. You will too.

Days 10-12

Madrid

Madrid is our final chapter, where art, power and culture reach their dramatic crescendo. Perhaps that’s why Hemingway returned to this great city again and again. It was certainly where Picasso’s fury and grief clarified into a single, unforgettable canvas, which hangs alongside the world’s greatest collection of Spanish art. It’s a looking place. You can’t not pay attention.

Day 10
“Just like the moving pictures”

Madrid is a change of key. Now it’s all wide avenues, terracotta rooftops, and a busy intellectual energy that buzzes through the air. Your home for the next three nights is The Palace – a grand early 20th-century hotel near the Prado, whose luminous stained-glass dome has welcomed statesmen, artists, and writers for more than a century. Hemingway immortalized its bar in The Sun Also Rises. Hang around for a while. Drink it in.

Day 11
"It was a fine morning"

Today you’ll visit the Prado – that towering temple to Spanish art. Stepping into its halls, your private guide will sketch the outlines of the masterpieces that shaped Picasso’s development, from Velázquez to Goya. These were stepping stones. They led him to a pictorial revolution.

You’ll eat lunch at Sobrino de Botín – a 1725 restaurant that Hemingway immortalized in The Sun Also Rises. A senior member of the team will greet you, sharing anecdotes about its literary patrons and archival photographs that’ll bring the past vividly to life. The cuisine here is elegantly Castilian: vivid, rich, precise.

Day 12
“Now I can enjoy everything so well”

Your final day moves on foot through Madrid’s nest of streets, tracing Hemingway and Picasso’s footsteps through bookshops, ateliers and studio spaces. These private visits will draw attention to the creative threads that stretch back to the 1920s. The city is still creating, still evolving.

Your trip’s final scene is more powerful still: where we’ll bring you to the Museo Nacional Centro de Arte Reina Sofía for a pilgrimage to Picasso’s Guernica – solemn and commanding. Your guide will describe its symbolism and emotional heft, situating it within the broader narrative of Spain’s turbulent history. Then silence. This is when the canvas speaks.

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