Annapolis, Maryland, the state capital, is a lovely historic coastal city located on the Chesapeake Bay. As it happened, we needed to file a few documents with the Secretary of State. Rather than mail the documents, we decided to make a day of it in Annapolis. Stay tuned because we have a story to tell about those documents, and it will be a good one.

Annapolis is a pedestrian friendly city, and since it’s a coastal city there are water ways and sailboats and yachts every which way you look. Oh, and Annapolis is home to the US Naval Academy. There’s a lot going on for a small city with a population of 40K+.

Annapolis Highlights

How do you spend a day in Annapolis? Here are just a few highlights from our day strolling through the historic city center, the waterfront and the naval academy. We were fortunate in that we had the best weather day. The sky was blue with puffy white clouds, and a gentle breeze kept it from being too hot. Just like we do in every city we visit, we let our feet lead the way.


We parked in the Gott Parking Garage at 25 Calvert Street. The prices are reasonable and it was so much easier than trying to find street parking. We paid $15 for 6 hours. Just around the corner from the garage is a visitors center and from there it’s an easy walk to the waterfront.

The State House

Just a few blocks from the parking garage you’ll find the state house with its impressive white steeple. It is the oldest state legislative house, still in use, in the country. That’s saying something, don’t you think? And, it also gives you an idea of just how long Annapolis has been around; the city was founded in 1649. A visit to the state house is well-worth the time.

  • There are security check points at the state house, tours are self-guided.

The Governor’s Mansion

The governor’s mansion, known as “Government House”, is located just across the street from the state house. Convenient, I’d say. Do you suppose there is an underground passage to the state house? The first governor of Maryland, Oden Bowie, moved into the mansion in 1870. Maryland’s newly elected governor, Wes Moore, and his family moved into the mansion in January 2023. He is the 63rd governor of Maryland.

  • Tours are available by appointment.
The “Government House” – Governor’s Mansion

Main Street & Francis Street

Probably the two most visited streets in Annapolis are Main and Francis both of which are lined with boutique shops, galleries and eateries. You name it, you’ll find it. It’s a shopper’s delight and a foodies paradise

Main Street

Continue along Main Street and you’ll find yourself at the waterfront. It’s a lovely spot to find a bench, rest your feet and embrace the moment. Eateries line the dock and sail boats come and go.

Alex Haley Memorial

Alex Haley wrote the the book, “Roots”. It was published in 1976. The memorial has a prominent place near the waterfront. It memorializes the place where Alex Haley’s ancestor, Kunta Kinte, arrived from Africa and was sold in to slavery.

Alex Hayley Memorial

The Maritime Republic of Eastport

Walking along the waterfront, merge on to Compromise Street and walk over the Spa Creek Bridge. The bridge, a bascule drawbridge constructed in 1946, connects Compromise Street on the Annapolis side to Sixth Street on the Eastport side. If you’re lucky you’ll time it just right to watch the bridge rise to let sailing ships pass through. It’s a comfortable walk, sidewalks on both sides. The views are wonderful.

CLICK HERE to watch our video of crossing the Spa Creek Bridge.

Lunch in Eastport

As mentioned, there are a plethora of eateries in Annapolis and Eastport. We made our way to Bread & Butter Kitchen and happily enjoyed two very good sandwiches, outdoors, with the harbor full of sailboats just across the road. Does it get any better?

Pinkney Street

Walk back across the Spa Creek Bridge, make your way to Pinkney Street and oohhh and aahhh over the historic row houses, all facing Pinkney Street. The Shiplap House is one of the oldest surviving houses in Annapolis dating back to 1715. In the 18th century it was a store and tavern. If you’ve ever heard of Joanna Gaines, you most likely know about shiplap.

US Naval Academy

Visitors are welcome to tour the grounds, although there are two entry points where visitors must go through a security check point and show ID. International visitors must show a passport. A very nice visitors center is filled with academy history, a short film that plays every 15 minutes, a gift store and restrooms.

The grounds of the academy are impressive, with green well-manicured lawns and gardens that border the Severn River. There are two must see places on the grounds. One is the Captains Row of historic homes and the other is the chapel. Even though it’s known as the chapel, I could argue the point. It is enormous, beautifully ornate, and seeped in history.

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  • 90-minute guided tours of the Naval Academy are available for a fee.

The lovely Captain’s Row – a 1:46 video.

St. Anne’s Parish

St. Anne’s Parish Church is lovely. It’s known as the church in the circle because it is just that. It literally sits in the middle of a circular roadway. Founded in 1692, it was the first church in Annapolis. Saint Anne is known as the patron saint of grandparents, mothers, married couples and the infertile.

I especially liked the individual needle point prayer stools because I think it speaks volumes about the parishioners throughout the history of the church. It is the only church we’ve visited, anywhere in our travels, with these unique lovingly-made stools.

How to Spend a Day in Annapolis

Annapolis is a lovely historic coastal city located on the Chesapeake Bay that offers visitors a wealth of experiences. If you find yourself in Annapolis, and really you should, take your own walking tour and see how it compares with ours.

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