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A Perfect 24 Hours in Annapolis Maryland

Greetings Internet Stranger and welcome to 24 hours in Annapolis! What a great choice for a place to spend a day or two off! Annapolis has so much to offer. After all, it is the capital of Maryland, and it’s the home of the Naval Academy. It’s a lovely, yet small city with an amazing collection of colonial buildings.

Most importantly for our purposes, it’s absolutely one of the best possible places to spend 24 hours. We’re going to dive right in and indulge in all the seafood, history, and also seafood that our brains and tummies can stand. Let’s go!

Want to cut right to the chase, Internet Stranger? One of the best things to do in Annapolis is this excellent paddleboarding lesson right here!

24 hours in annapolis

24 Hours in Annapolis

Where to Stay

When I enjoy 24 hours in Annapolis, I recommend staying at the Inn on Main Annapolis. It has a perfect location within walking distance of pretty much anything you’d want to see in Annapolis. It has free WiFi, which is important to me, as I am always working when I travel. Working hard to find delicious and beautiful things for you, my dear Internet Strangers.

And speaking of delicious, the breakfast is excellent as well. I indulged in yogurt, fruit, and lashings of hot coffee every morning before starting my day, but they have tasty hot foods also. Finally, compared to many hotels in Annapolis itself, it’s quite affordable.

If you’re looking for an excellent deal on this hotel, click here.

If you’d rather explore great deals on other hotels in Annapolis, click here!

This search engine will help you find the perfect place to stay during your time in Annapolis. With plenty of options to choose from, I’m sure you’ll find something for your schedule and budget.

24 hours in annapolis

24 Hours in Annapolis

Morning: Explore Historic Annapolis

Annapolis is an impressively historical town with many buildings that date back to colonial days. So why not start your 24 hours in Annapolis with a self-guided tour of all the most important Colonial sights and attractions?

Fortunately you have the very reliable ME as your guide, and I’ve been going to Annapolis since I was a child. Let me get you started on your self-guided tour with…


24 hours in annapolis
1) Maryland State House

As I mentioned earlier, Annapolis is the capital of the state of Maryland. That means the Maryland State House is in Annapolis. Of course, the State Senate makes all the important decisions affecting Marylanders, like choosing the most delicious way to prepare crab or selecting the very best season of The Wire.

Annapolis is the only city to have all the original homes of its signers of the Declaration of Independence intact. You can find their portraits in Annapolis’s super schmancy state legislature chambers and indeed all over Annapolis. 

24 hours in Annapolis

If you really want to impress a local, tell them you already know that Maryland’s signers of the Declaration of Independence are Chase, Stone, Paca, and Carroll. You might even pass for a local yourself by dropping that kind of knowledge bomb.

If you’re a fan of cravats, don’t miss the colonial portrait room in the State House. Many portraits of prominent colonial Marylanders were done by painter Charles Willson Peale and I really admire his ability to find the beauty in stuffy middle-aged rich dudes.

24 hours in annapolis

The Maryland State House has also taken more steps recently to teach about Maryland’s rich Black American history.

Statues of Harriet Tubman and Frederick Douglass commemorate the end of slavery in Maryland. (Both Tubman and Douglass were born in Maryland and fought fiercely to help enslaved people and end this vicious system.)

24 hours in annapolis
2) See the Maryland Flag

I’m sure every state flag has a story, but I’m equally sure that I usually don’t know what that story is. I wouldn’t recognize my home state of New York’s flag if it bit me. (Although if any state’s flag knew how to bite, I’m sure it would be New York’s. We’re a tough bunch!)

But I digress. Allow me to share with you the sad history of Maryland’s bifurcated flag. During the Civil War, Maryland was divided. Some of its people supported the Union, and some supported the Confederacy, though Maryland was not the Confederate state. After the war, to represent unity, both flags were put on the state flag.

The red is for the Confederate side and the yellow the Union side, but actually both sides of the flag were originally symbols of Lord Baltimore back in colonial times. In Maryland everything seems to come back to Lord Baltimore. He’s like the Forrest Gump of Maryland.

24 hours in annapolis
3) Take a Tour of the Hammond Harwood House

Our next stop is just a short walk from the Maryland State House. The Hammond Harwood House is one of the prettiest colonial houses I have ever seen. It was so pretty that Thomas Jefferson liked to sketch it for fun. You need to visit on a group tour, and I’d suggest reserving in advance if you can.

The HHH was designed for Matthias Hammond to be his home with his newly engaged bride. But sadly Hammond’s fiancee kicked him to the curb for another man after he lost a local election, and Hammond never actually moved into the house.

I can’t respect that decision. If I had gotten dumped, I would have thrown a ton of parties for all the eligible ladies in Annapolis just to show them what a sweet pad they’d be getting if they married me. Suck on that, fair weather fiancee!

24 hours in annapolis hammond harwood house

My favorite room in the HHH is the kitchen. I always like seeing the kitchens of historic homes because they are so different from modern kitchens. In Colonial Annapolis they weren’t allowed to have ovens because of the fire hazard.

Enslaved people would have worked in these kitchens preparing meals for the family. Our guide told us that one of the owner’s of the house ran into financial troubles and tried to sell two enslaved girls, even though their mother was free. She successfully sued for and won their freedom, but most of the other enslaved servants weren’t so lucky.

24 hours in annapolis

After visiting the downstairs, you’ll head upstairs and learn more about the lives of the families that owned this house. The dining room would have been one of the most expensive rooms because it was meant for entertaining.

You can tell because of the elaborate molding on the walls and the beautiful paint. Basically any room that has fancy molding is for guests and any room with plain molding was for the family only. I guarantee that your docent will quiz you on this subject. (That’s not a joke.)

soapsuds alley
4) Soapsuds Alley

The self-guided tour ends here, so I can explain why this cute street has such a weird name. Its real name is Pinkney Street, but it was nicknamed Soapsuds Alley because many women on this street took in laundry.

It is a perfect place for this part of our 24 hours in Annapolis to end because one of the little homes on this street, the Hogshead, is now a little space where historical re-enacters can show you about different aspects of working/middle-class colonial life. Just keep in mind that these guides are only around on weekends at the moment, so you might just be able to see the exterior if you come by on another day.

On the day I visited, there was a woman playing the role of a colonial shopkeeper. She passed around all the materials a shopkeeper might use, like this deer horn.

A Perfect 24 Hours in Annapolis Maryland 1

I imagine this deer horn would come in very handy when the British attack. The colonials were so practical like that.

24 Hours in Annapolis

Afternoon: Feast on Seafood!

I don’t need to tell you that seafood is what’s on the menu in Annapolis! That’s why we are so lucky that Annapolis Eventours offers an amazing seafood-based tour of the city. You can book it yourself by clicking here.

This tour runs on this cute little electric cars, so you can see all of the city during your 24 hours in Annapolis without having to strain your feet too much. Along the way we’ll fill our bellies with deliciousness and our heads with…


24 hours in Annapolis
1) What is a CRAB PRETZEL?

The first stop at Davis Pub is actually my favorite. We got to chow down on a local specialty, the crab pretzel, which is broiled crab dip on a giant pretzel base. This is surely the greatest thing to come out of Maryland since…Cal Ripken Jr? I don’t really know anything else that has come out of Maryland.

The crab pretzel is both classy (so much real seafood) and shameful (so much fat!) in a way that I can really get behind. Plus you can order a drink on your own expense! I had a local beer, but one of the other ladies on the tour got a cute mini bottle of Prosecco. (The pub also has some nice booze-free Arnold Palmers.)

PS. I recommend saving half of the crab pretzel for breakfast the next morning if you get one to yourself. They’re really much too big to finish, especially since we are going out for dinner tonight. We don’t want to miss a single mouthful of seafood.

2) What kinds of seafood can I find in Annapolis?

Answer: ALL the seafood! I’ve been to Annapolis several times, and I’ve feasted on crab, lobster, oyster, and many varieties of fish. But the next food stop is at a pub called Stan and Joe’s for some of the only seafood I had never tried in Maryland: the massive and succulent green mussel.

This is the sort of place I wouldn’t have visited if I hadn’t been on a food tour because the outside didn’t look like anything special. Fortunately the mussels were as good as advertised. It was especially fun to soak up the broth with the warm, fresh bread. I like any food that encourages you to play with it.

24 hours in annapolis
3) Where can I experience fine dining in Annapolis?

Annapolis isn’t known for being a fine dining destination. That’s why it is a fun treat to stop in at one of the few fine dining restaurants in the area, Harry Browne’s. We were treated to some creamy, decadent lobster bisque.

As I ate it, I felt like some big-shot Annapolis powerbroker, organizing a deal to get the colonial guides funnier tri-cornered hats, or whatever it is Annapolis powerbrokers do. I really want to know why cream and shellfish go so well together. Surely some food scientist has figured this out.

24 hours in annapolis

24 Hours in Annapolis

Late Afternoon: On the Waterfront

If you go to Annapolis and don’t spend some time cruising on the water, I will have no choice but to call you a Silly Billy. The only excuse would be if you go to Annapolis in January, but why would you want to do that? All the tourist attractions will be closed and all the seafood will be stuck underneath the ice, so the only thing there will be to do is attend meetings of the Maryland General Assembly.

During the summer, there are many cruises you can take, but I chose this one because it leaves in the late afternoon and I find that those are precisely the hours when I want to be sitting peacefully on a boat looking at the water.

You probably don’t think there’s a lot to know about a bunch of water off the coast of Maryland. Well, allow me to enlighten you!

24 hours in annapolis

The coolest attraction you’ll see on your boat cruise is the Naval Academy. The Academy was closed to tourists the last time I visited, so this might be your best chance to see it. Tons of famous people have gone here, including former President Jimmy Carter and the late Senator John McCain.

24 hours in annapolis

There is kind of a rivalry between this school and the non-Naval College in Annapolis, St. Johns. But we will learn more about St. John’s tomorrow. For now, there’s no learning! Buy a drink at the bar on the boat and enjoy the waters of Annapolis!

24 Hours in Annapolis

Evening: Dinner at O’Leary’s

If you’re going to have dinner in Annapolis, I say go seafood or go home. And O’Leary’s is definitely one of the best places for seafood in Annapolis. According to my Uber driver, a lot of locals go here, so you know that means the food is tasty.

24 hours in annapolis

It isn’t oyster season during the summer, so if you’re visiting at that time, it’s best to get your oysters cooked. That’s why I recommend their specialty dishes like the buffalo oysters for your appetizer. (Yes, that’s oysters in buffalo sauce, and it’s exactly as delicious as it sounds.)

24 hours in annapolis


Of course it is a crime under Maryland Penal Code Section 28.7 to leave the state without consuming a crab cake. I like the crab cakes at O’Leary’s because there is not too much breading on them, so you can really taste the fresh crab.

I tell you, Maryland has almost spoiled me for eating crab anywhere else. Curse you, Marylanders and your abundance of crustaceans and your inability to enunciate your consonants!

24 hours in annapolis

For dessert I had this rich butterscotch pudding to balance out all that healthy seafood. It wasn’t too sweet, so it was the perfect end to a decadent day full of seafood delights.

And hopefully you’ll find it to be a perfect conclusion to your 24 hours in Annapolis. In just one day, we’ve had crab, mussels, clams, oysters, and more crab! A perfect Maryland experience!

24 hours in Annapolis

24 Hours in Annapolis

What to Pack

  • An excellent small cell charger so you can keep taking pictures all during your 24 hours in Annapolis
  • The best full-length guide to the state of Maryland
  • The most reliable travel umbrella that is small enough to fit in my purse, but strong enough to stand up to powerful winds
  • These great TSA approved clear toiletries bags, so I can always keep spare toothpaste and travel sized toiletries in any carry-on.
  • My book Get Lost, that I wrote myself with all my best travel tips. This book will show you how travel can take you on a journey of self-discovery.
24 hours in annapolis

24 Hours in Annapolis

How to Get There

By Car: This is the easiest way to get to your 24 hours in Annapolis. I personally don’t know how to drive, but if I did, this is the route I would choose. If you need to rent a car, you can use the search engine Expedia to find the best price from the available car rental companies.

By Plane: The closest airport to Annapolis is Baltimore, so you can fly into this airport and then drive or take an Uber from the airport to Annapolis. (Again, I recommend using a search engine like Expedia to search for the best prices on flights.)

By Train or Bus: Flixbus has finally started a bus service from NYC, DC, and Richmond to Annapolis! Yay! That means that if you can get to those cities by train, you can easily get to Annapolis by bus.

Or you can take a train to Baltimore and then drive/Uber to Annapolis. (The Uber price really isn’t that expensive and the drive is about 45 minutes.) As of now, there are no trains that will take you directly to your 24 hours in Annapolis.

That’s a Perfect 24 Hours in Annapolis, Maryland

What would you do with 24 Hours in Annapolis? Would you like more suggestions for hotels to choose? And what does the Maryland State House think is the best season of The Wire? Email me at and let me know.

Note: If you want to know how I put my travel itineraries together, just click here. Keep in mind that while each article is about how to spend 24 hours in a place, that doesn’t mean you should ONLY spend 24 hours in Annapolis. If you have an extra 24 hours in Annapolis, try this itinerary.

A Perfect 24 Hours in Annapolis Maryland 2
  1. […] history, nothing stands out more than our Star Spangled Banner. This is the flag that inspired Marylander Francis Scott Key to write our national anthem. He was inspired when he saw the flag stay strong […]

  2. […] A Perfect 24 Hours in Annapolis Maryland […]

  3. […] So many things! President Carter, as he was fond of reminding people, was born on a simple peanut farm in Plains, Georgia. (When he became president, he turned his peanut farm over to a blind trust to avoid a conflict of interest.) Carter was the first person in his family to get a degree of higher education. He dreamed of entering the Navy and graduated from the Naval Academy in Annapolis, Maryland. […]

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