Welcome to the nation’s capital—a city shaped by movements and institutions, home to vibrant neighborhoods and global communities, where debates over democracy unfold not only in chambers of power, but in restaurants, music venues, and everyday public life.

Our first day situates the current moment in the United States within two essential frames: the global retreat of democracy and America’s own long, unfinished struggle to realize its democratic ideals.

We begin our journey together at noon with a welcome lunch at Immigrant Food, a restaurant that celebrates the delicious flavors of global cuisines immigrants have brought to the United States throughout its history.

Afterwards, we gather for an intimate conversation with a leading authority on global democratic trends. We explore how these trends are measured, where the United States fits within global patterns, and why international comparison matters for understanding democratic erosion at home.

We make our way to dinner with a walking tour through Blagden Alley, a 19th-century network of services alleys behind grand rowhouses that once housed formerly enslaved people and domestic workers. Today, it is home to some of the city’s most distinctive restaurants. Over a shared feast at Supra, Washington’s celebrated Georgian restaurant, a former Deputy Assistant Attorney General will draw on decades inside the executive branch to examine how moments of national strain test the rule of law and the guardrails that constrain executive power. Drawing on experience across administrations, he will offer and insider’s perspective on how constitutional norms are preserved or pressured during periods of upheaval.

In the evening, we board a private, guided sunset cruise on the Potomac River, viewing the city’s iconic monuments from the water over a glass of wine. This quiet moment offers space to reflect on the visible symbols of democracy and the often unseen forces that shape how power is exercised.

Accommodation: Eaton DC

Our second day centers on the institutional foundations of American democracy—the checks and balances designed to restrain executive authority—and what happens when they are strained.

We begin the morning on Capitol Hill with those working inside one of the most consequential, and increasingly constrained, institutions of American democracy. Following a private tour of the U.S. Capitol, we gather for an off-the-record discussion led by a former senior congressional official, offering his perspective on whether Congress’ role in balancing executive and judicial power has eroded under the Trump administration and what that means for the future.

The morning continues with a conversation with a member of Congress providing a rare, behind-the-scenes view of navigating polarization with a focus on strategy and adaptation in today’s constrained congressional environment. Drawing on firsthand experience, we explore how shifts in power, procedure, and political incentives have reshaped Congress’s ability to act as a check.

Over lunch, we will meet with a commissioner from the U.S. Election Assistance Commission to discuss the most pressing threats facing the 2026 midterm elections—both to their administration and to public confidence in their legitimacy—and how the Commission is working with state and local officials to prepare for and mitigate those risks.

Later in the afternoon, we will have a drink with a former senior White House and Executive Branch attorney now litigating prominent cases against the current administration. He offers an insider look at how recent executive actions are testing constitutional guardrails and what it takes to contest those actions from within the legal system.

The evening is yours to explore. Descend into the Dupont Circle Underground, a former streetcar station reimagined as a contemporary art space; have a signature Mint Julep at the Round Robin Bar, long frequented by presidents, diplomats—and those quietly observing them; or catch live jazz at Blues Alley, the nation’s oldest continuing jazz supper club, where legends like Dizzy Gillespie and Eva Cassidy once performed.

Accommodation: Eaton DC

Today examines how freedom of expression operates across journalism, cultural institutions, and the shared civic spaces where ideas and identities are shaped.

We start the day at National Public Radio headquarters where we hear about current threats to public media, including political pressure, funding challenges, and efforts to undermine public trust in journalism. Our conversation with a senior journalist focuses on how journalists and institutions are responding—what strategies are working, what is at risk, and why independent media remains essential to democratic resilience. 

In the afternoon, we head to the iconic Smithsonian Institution for a private tour focused on its founding mandate “to increase and diffuse knowledge” at its earliest buildings, the Castle and the Arts and Industries Building. We then meet with a senior Smithsonian museum leader whose institution highlights overlooked stories of individuals and communities across the Greater Washington, DC region who have used collective action to advance a more equitable future. The conversations will address how the museum continues to research, interpret, and present these narratives amid funding constraints.

That evening, we gather for dinner at a favorite Washington restaurant by Chef José Andrés, joined by a James Beard Award–winning, New York Times bestselling writer who helped pioneer the field of culinary diplomacy. Over dinner, we explore how food functions as a tool of cultural exchange, soft power, and democratic engagement in Washington and around the world. 

Accommodation: Eaton DC

On our final day, we examine how rights are defended, how individuals and communities build resilience under strain, and how renewal takes shape in unexpected places. Rather than focusing on a single issue area, we explore the interconnected ways legal protections, civic culture, and personal well-being reinforce or weaken one another.

We begin the morning with a senior leader from a nationally respected civil liberties organization for a candid discussion about defending liberty at scale. Drawing on experience across multiple rights areas, they offer a behind-the-scenes look at how threats to freedom emerge, how decisions are made about when and where to intervene, and why cases involving marginalized communities often shape protections for everyone.  

Over lunch, we speak with a Pulitzer-Prize-winning journalist who studies the relationship between mental health and democracy. She will talk to us about the social and political forces and narratives that keep people isolated and unwell, the work she is doing with journalists and creators to cultivate civic resilience, and tools we can adopt as content consumers to break stress patterns and stay grounded.

We conclude mid-afternoon with a reflective wrap-up at Republic Restoratives Distillery, a venue that illustrates how people build community around shared civic values, ethical enterprise, and economic inclusion. Together, over cocktails made with Fascist Tears vodka, Dissent gin, or Purpose rye, we reflect on what our journey together has revealed about the fragility of liberty—and the many ways individuals and institutions respond with resilience, creativity, and resolve.