Spend a Day in Annapolis

If you’re craving coastal charm, rich history, and fresh seafood, a day trip to Annapolis is the perfect escape. Just under an hour from D.C., this quaint waterfront town is bursting with colonial beauty and maritime spirit. Here’s how to make the most of a day in Maryland’s capital.

Start with Breakfast Downtown

Ease into the day with breakfast at Iron Rooster, known for its all-day brunch and homemade pop tarts. From fluffy pancakes to crab hash, it’s the perfect fuel for a full day of exploring.

Stroll Through Historic Streets

After breakfast, wander the cobblestone streets of downtown Annapolis. You’ll find beautifully preserved 18th-century homes, charming storefronts, and the iconic Maryland State House—the oldest one still in legislative use. Don’t miss Main Street, where boutiques and gift shops offer everything from nautical décor to locally made jewelry.

Take to the Water

A visit to Annapolis isn’t complete without getting on the water. Book a short harbor cruise or set sail on a historic schooner for an hour-long tour of the Chesapeake Bay. Prefer to stay land-bound? The City Dock offers great people-watching and serene views.

Lunch with a Side of Crab

When hunger strikes, head to Cantler’s Riverside Inn or Mason’s Famous Lobster Rolls. Annapolis takes its seafood seriously, and blue crab is the star of the show. Whether steamed, in a dip, or as a cake, you can’t go wrong.

Explore the U.S. Naval Academy

In the afternoon, take a guided tour of the U.S. Naval Academy. The grounds are beautiful and steeped in history. Don’t forget to stop by the gift shop for unique Navy-themed keepsakes.

Golden Hour at the Marina

As the sun starts to dip, head to Annapolis City Marina or grab a drink at Pusser’s Caribbean Grille, where the waterfront views are unmatched. Sip a rum punch and soak in the golden glow reflecting off the boats.

Dinner and Dessert

Wrap up your day with dinner at Osteria 177 for Italian fine dining or Boatyard Bar & Grill for a laid-back seafood feast. Before you head home, swing by Kilwins for a scoop of homemade ice cream or fudge to go.

Whether you’re drawn by history, sailing, or seafood, Annapolis has a little something for everyone. It’s the kind of place that invites you to slow down and savor each moment—one cobblestone and crab claw at a time.