Some say Annapolis is a town with a “sailing problem.” But it’s an addiction that no one apologizes for, because it’s made this city the “sailing capital of America.” Set on the biggest estuary in the nation, the Chesapeake Bay, Annapolis boasts 17 miles of shoreline. Thousands of locals dock their boats at the piers and marinas along this waterfront. And thousands more visit here by boat every year to cruise, race, fish, and stand-up-paddleboard.

On the end of the steps near the water’s edge, you’ll see lifelike bronze sculptures of a man reading a book to children. This is Alex Haley, author of the bestselling novel Roots: The Saga of an American Family. You might have seen one of the TV series based on the book. The final episode of the first series, which aired in 1977, was the third highest telecast of all time.

The United States Naval Academy was originally founded on the 10-acre Fort Severn Army post and just called the Naval School. The school’s first class of 50 students, known as midshipmen, began studies in 1845. Within less than two decades, the academy found itself in the midst of a crisis. The coming Civil War tested its very loyalty and commitment to the Union. The issue of secession moved like a cloud over the academy. Many of its students hailed from Southern states, and a great number had ties to families and communities sympathetic to the Confederacy.

This Colonial-era home and its famous gardens offer a peaceful respite from the busier parts of Annapolis. But don’t be fooled. The man who lived here in the mid-18th century was one of the city’s most notorious rabble-rousers!

Many people call this home's entrance the most beautiful door in America. But this isn’t the house’s only fascinating door. Inside, you’ll find three so-called “doors to nowhere,” which were common at the time of the house’s construction. They look like regular doors, but if you could open them, you’d find solid walls behind them.

St. John’s College might look like a classic university, but it’s actually known as “the most contrarian college in America.” That’s because it has thrown out every modern idea of higher education. There are no majors here. No professors. No syllabi. There are no fancy study cafes. There’s not even a football team! Instead, small groups of very intense, highly focused students—called Johnnies—follow a daily, simple formula: Read. Discuss. Repeat.

The Maryland State House is the only state house to have also served as the nation’s capitol. The Continental Congress met here from November 1783 to August 1784. On December 23, 1783, George Washington stood before the Congress here to deliver a historic speech to the new nation: one that would forever shape the future of the United States.

The Maryland Inn was built in 1776 as a private home—one of the finest on the Chesapeake. But for most of its lifetime, it’s been a hotel. If you have time, step inside. You can see the so-called evidence of a myth that Annapolitans love—the legend of underground tunnels that many claim once connected the oldest buildings of Annapolis.

The current structure of St. Anne’s Episcopal Church was completed in 1859, but its congregation dates to the 1690s. The inscription on the base of the lectern memorializes a sailor named James Waddell, who played a key, yet surprising, role in the ending of the American Civil War.

This museum is named after three heroes of African American history. One of the better known of the three is the great social justice warrior Frederick Douglass. Another is Harriet Tubman, famous for her role in the Underground Railroad. The museum’s third namesake, Benjamin Banneker, may not be so familiar to those outside of Maryland. But he should be. Banneker was America’s first known Black scientist.