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. Over lunch, we gather for an intimate, facilitated 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.

In the afternoon, we travel to President Lincoln’s Cottage, where Abraham Lincoln spent nearly a quarter of his presidency grappling with the moral and political questions that would culminate in the Emancipation Proclamation. In this reflective setting, we hear from a scholar of American political history and democratic crises, who traces how moments of national upheaval have tested executive power, constitutional guardrails, and the meaning of freedom—drawing connections between past democratic breaking points and the pressures facing the country today.

After dinner at a historic Washington restaurant, 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.

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, guided visit 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. Drawing on firsthand experience, we explore how shifts in power, procedure, and political incentives have reshaped Congress’s ability to act as a check.

The morning continues with a candid conversation with a member of Congress—or a senior staffer if the Congressperson is pulled away—providing a rare, behind-the-scenes view of how they advance an issue they care deeply about while navigating polarization, leadership control, and public scrutiny, with a focus on strategy and adaptation in today’s constrained congressional environment.

In the afternoon, we will meet 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.

Today focuses on freedom of expression as both a core democratic safeguard and cultural practice. 

We start the day at a major national newsroom where we hear about current threats to public media, including political pressure, funding challenges, and efforts to undermine public trust in journalism. The conversation 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. 

After lunch, we visit the Go-Go Museum & Café, where we explore Washington’s homegrown musical movement and its deep roots in Black identity, community life, and political expression. In conversation with a leading voice from the go-go movement, we examine how go-go has long served as a space for organizing, resistance, and shared memory. 

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. 

On our final day, we step back to examine how personal liberty is defended when legal protections and democratic guardrails are under strain. Rather than focusing on a single issue, we explore how challenges to individual rights—across speech, privacy, bodily autonomy, freedom of movement, and equal protection—often follow similar patterns, and how they are confronted from inside the system. 

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.  

After a final group lunch, we turn from the big picture to the front lines, meeting with a legal advocate working directly with individuals navigating the immigration system. Through concrete examples, they show how federal enforcement decisions play out in real lives, how due process is tested in everyday practice, and how local actors work to uphold fundamental protections when national systems falter. 

We conclude mid-afternoon with a reflective wrap-up in a venue that illustrates how people build community around shared civic values, ethical enterprise, and economic inclusion. Together, 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.