Visitors to Annapolis find a vibrant city, proud of its heritage and charm, offering the latest in dining and shopping, unique sightseeing, and entertainment. Since its founding as a colonial Chesapeake Bay seaport, Annapolis has emerged as the sailing capital of the world, home to both the US Naval Academy, the third oldest college in the country, and the Maryland state capital.
Attractions to Explore
The Historic District
The waterfront historic district is a well-preserved colonial seaport with cobblestone streets and more original 18th century structures standing than any other city in the United States. Many of the Founding Fathers visited the city, including George Washington, who traveled to Annapolis to resign his commission in the Maryland State House when the city briefly served as capital as the United States. Today, this easily walked historic district presents a blend of preserved structures, museums, restaurants, shops, live music, and nightlife. Throughout the historic district you will find a mix of visitors, groups on walking tours, uniformed Navy midshipmen, people in colonial garb, working and recreational boats, legislators, sailboat race crews, statues, and public art.
The US Naval Academy
A visit to Annapolis isn’t complete without stepping onto the historic grounds of the US Naval Academy, located just a short walk from the Aarcher Institute training center. Founded in 1845, the Academy remains an active military campus and a defining part of the city’s identity. Guests can join guided tours to explore iconic landmarks, learn about midshipman life, and experience the Academy’s deep maritime heritage.
Sailing on Schooners
Annapolis is known as the sailing capital of the world, and a two‑hour sail aboard the Woodwind or Liberté schooners is one of the most memorable ways to enjoy the Chesapeake Bay. These classic vessels depart from the waterfront and offer a relaxing, scenic experience that’s perfect for unwinding after a day of training. You’ll take in harbor views, historic shoreline architecture, and a lively mix of working and recreational boats that define Annapolis.
Harbor Queen Tours
For a different perspective on the city, the Harbor Queen provides a narrated cruise through Annapolis Harbor and the Severn River. This enjoyable tour highlights the city’s maritime history, the Naval Academy’s shoreline, and bustling City Dock area. It’s an ideal low‑key activity within steps of the historic district and a great way to see Annapolis from the water without needing to learn how to sail yourself.
Explore Washington, DC
With Washington, DC just a 40‑minute drive from Annapolis, many visitors extend their stay to explore the nation’s capital. Whether you’re interested in museums, monuments, or government landmarks, DC offers endless options for a full-day or evening trip. After training, it’s easy to head into the city for sightseeing, dining, or cultural experiences before returning to the quiet charm of Annapolis.