Why Visit Annapolis: Maryland’s Seaside Treasure Full of History

When you think of iconic East Coast destinations, you might picture Boston’s cobblestones, Charleston’s antebellum charm, or the bustle of Washington, D.C. But sitting quietly by the Chesapeake Bay is a city that effortlessly blends all of those vibes with a maritime flair that’s completely its own. Annapolis, Maryland is a place where colonial architecture, seafood feasts, sailboats, and history all come together — and somehow, it just works.

Whether you’re into American history, sailing, seafood, or simply soaking up small-town charm, Annapolis is the kind of place that offers something for everyone. And if you’ve never been? You’re seriously missing out.

The Sailing Capital of the U.S.

Let’s start with the obvious: Annapolis is one of the top sailing destinations in the entire country. Known as the “Sailing Capital of the U.S.,” it’s home to world-famous regattas, bustling marinas, and some of the most picturesque waterfront views on the East Coast. Even if you’ve never stepped foot on a boat before, there’s something magical about watching dozens of sailboats catching the wind on the Chesapeake Bay as the sun sets in the background.

Want to get in on the action? You can hop on a public sailing cruise, charter a private boat, or even take lessons from local pros. If you’re visiting in October, the Annapolis Boat Show is a massive event that draws boat lovers from around the world and turns the waterfront into a floating showroom.

A Walk Through American History

Annapolis isn’t just about sails and seafood — it’s also one of the most historically rich cities in the country. Founded in 1649, it served as the temporary capital of the United States in 1783–1784. In fact, it was here that George Washington resigned his commission as commander-in-chief of the Continental Army — a moment that signaled the true beginning of American democracy.

The Maryland State House, located right in the heart of town, is the oldest state capitol still in continuous legislative use and the only one ever to have served as the nation’s Capitol. It’s open to the public and free to explore. Just walking the streets of the Historic District feels like stepping back in time, with its cobblestone streets, Georgian buildings, and gas-lit lamps.

Bladen street over Maryland State House capitol building and site of many historic events build in 1779 Annapolis MA, USA / Sergey Novikov / Shutterstock

Home of the U.S. Naval Academy

One of the crown jewels of Annapolis is the United States Naval Academy. Not only is it an elite institution training future Navy and Marine Corps officers, but it’s also one of the most beautiful campuses in the country. Visitors are welcome to take guided tours and see highlights like the Naval Academy Chapel, the crypt of John Paul Jones (the “Father of the U.S. Navy”), and the impressive museum showcasing naval history.

During the school year, you might even catch the midshipmen marching in formation — a daily tradition that adds to the unique character of the town.

A Food Scene Anchored in Flavor

Let’s talk food — because Annapolis knows how to eat. If you’re a seafood lover, this is your paradise. The city sits right on the Chesapeake Bay, so it’s no surprise that blue crabs, oysters, and rockfish are local staples. Whether you’re picking crabs on a paper-covered table or slurping oysters fresh from the shell, it doesn’t get more authentic.

Be sure to stop by Cantler’s Riverside Inn, a legendary local spot where boats dock right at the pier and steamed crabs are served up by the bushel. Prefer something a little more upscale? Restaurants like Osteria 177 and Vin 909 offer incredible meals that fuse Chesapeake ingredients with international flair.

Pro tip: In the summer, grab a cocktail and some seafood at one of the dockside bars and watch the boats come and go. It’s the ultimate Annapolis vibe.

A Charming Downtown That’s Perfect for Wandering

Downtown Annapolis is the kind of place where you can spend hours just strolling. The historic waterfront is lined with boutique shops, galleries, ice cream parlors, and bookstores — all housed in buildings that date back to the 18th century. It’s walkable, scenic, and filled with character at every turn.

Take a lazy afternoon to explore Main Street, where you’ll find everything from handcrafted jewelry to nautical-themed art. Grab a coffee, people-watch by the harbor, or pop into Kilwins for a scoop of homemade fudge or a caramel apple that’ll take you right back to childhood.

Surprising Facts About Annapolis You Probably Didn’t Know

Here’s one for the trivia fans: Annapolis has more original 18th-century buildings than any other U.S. city still in use today. That’s right — it even beats out Colonial Williamsburg.

Another fun fact? Despite its small size, Annapolis was briefly the capital of the United States. For a few months after the Revolutionary War, Congress met here before heading to Washington, D.C.

And get this — Benedict Arnold, the infamous traitor of the American Revolution, once lived in Annapolis. His house still stands and is now privately owned, blending right in with the city’s colonial charm.

Festivals, Music, and That Chesapeake Spirit

Throughout the year, Annapolis comes alive with events that showcase its love of music, food, and maritime culture. From the Annapolis Film Festival to the First Sunday Arts Festival, the city always has something going on.

The annual Lighting of the Boats in December turns the harbor into a floating parade of lights, complete with music, food vendors, and all the festive spirit you could hope for. And during the summer months, live music spills out onto the streets, from jazz trios at the City Dock to bluegrass bands at outdoor beer gardens.