A Perfect One Day in Annapolis Itinerary

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Greetings Internet Stranger! I promise that this one day in Annapolis itinerary can help you live your dreams. If you’re anything like me, Internet Stranger, you’ve often wanted to take a time machine to explore the birth of our country. You’d like to get back there and party like it’s 1699 at the William Paca House.

Or perhaps you’d rather give the assorted Founding Fathers and Mothers a piece of your mind. You can always head over to a place like Colonial Williamsburg and see their historical reenactments.

But is there a modern city that allows you to revisit the past? The answer is Annapolis, Maryland. This perfectly preserved early American city is also a thriving state capital, so you can enjoy a one day in Annapolis itinerary, soaking up all that history without feeling like you’re in a theme park. Come with me and I’ll show you how to put the YOLO back in Colonial.

One Day in Annapolis Itinerary

Where to Stay

When I go to Annapolis, I stay at Gibson’s Lodging. It has a perfect location on charming Prince George Street, which is 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. 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! You’ll have tons of options to choose from, so I guarantee you’ll find something amazing in your price range.

One Day in Annapolis Itinerary

What to Pack

  • Comfortable and adorable sandals for summer (Annapolis can get hot as a spicy Crabby Patty)
  • Stylish boots for rainy days that you can wear from the capitol in the morning to oysters at night.
  • An excellent small cell charger so you can keep taking pictures of Annapolis all day
  • A light rain jacket because YOU JUST NEVER KNOW
  • The best full-length guide to the state of Maryland
  • Do not pack crab. They have plenty in Annapolis.
  • The definitive history of the city of Annapolis
  • A safety purse that looks cute so you can accessorize and protect yourself from colonial pirates

One Day in Annapolis Itinerary

Morning: Explore Annapolis

Are you ready to get exploring? Of course you are! That’s why you came here! And I’m ready to take you with…

approximately top 5: One Day in Annapolis Edition

One Day in Annapolis Itinerary
1) Saint Anne’s Church

The lovely St.Anne’s Church is not always open, and it wasn’t open on this particular day. However I can still give you some history of the building. Annapolis has always been the yin to Baltimore’s yang in Maryland, especially when it came to matters of religion. Baltimore was founded by the Catholic Lord Baltimore, so Annapolis became a haven for Protestants in Maryland. That’s why St. Anne’s is a Protestant church.

My favorite thing about the church was the cemetery with graves of prominent Annapolitans. One man came over from England a pauper and pretended to be a doctor even though he had no medical experience. He apparently became a great success and made a lot of money without anyone finding out that he wasn’t really a doctor. This sounds like the plot of an amazing TV show, perhaps starring Hugh Laurie.

Streets of Annapolis
2) Streets of Annapolis

Annapolis was a little bit wild back in the colonial days. Apparently wealthy young Marylanders liked to race their horses in the street. Horse racing was so popular in Annapolis that even the local government would sponsor horse races. So it wasn’t an uncommon sight to see horse races take place all over Maryland’s capital. (The streets of Annapolis aren’t usually as crowded as the photo you see above. The First Sunday art festival was in town the weekend I was there.)

Nowadays, horse racing remains popular in Maryland. In fact, you might have heard of a little horse race called The Preakness Stakes that takes place in Baltimore every year. (For those of you who don’t play the ponies, the Preakness is the second horse race in the Triple Crown, right after the Kentucky Derby.)

maritime eastport
3) Explore Maritime Eastport

After Saint Anne’s Church, I crossed a bridge from Annapolis into the neighboring community of Eastport. Eastport is officially the Maritime Republic of Eastport and that all businesses there must have some link with the sea. I think that’s so cool that any community dares to be that weird in this day and age. And the maritime affiliation certainly results in a plethora of outstanding seafood restaurants, so it’s really a win for us all!

annapolis harbor
4) Annapolis Harbor

You can’t leave Annapolis without spending some time by its lovely harbor. In Annapolis’s fishing heyday, there would be 100 boats in the harbor at a time. People can still fish in the harbor. But of course they need to watch out for overfishing, especially when it comes to one of Maryland’s beloved seafood delicacies, the oyster. That’s why you’re not supposed to eat oysters out of season.

If you’re unsure of whether or not oysters are in season, check that the month has an R in it. If it does, eat all the oysters you want! But if there’s no R, you should probably abstain. But if you’re not sure whether or not the month has an R in it, you have bigger problems than this blog can help you solve.

reynolds tavern
5) Reynolds Tavern

The Reynolds Tavern is one of the most historic buildings in Annapolis. It dates all the way back to 1747. It’s also a fun spot to go for dinner or tea. I very much enjoyed my meal there, except for when a moth got stuck in the restaurant and the waiters had to spend 20 minutes trying to chase it out.

The most famous client of the Reynolds Tavern was definitely one Mr. George Washington. Yes, Mr. “I Cannot Tell a Lie Because I Am the Father of Our Country” got his drink on here. Even more scandalously, he apparently had a crush on the mistress of the house, Maria Reynolds. Her older husband did not approve of the handsome young George making eyes at his wife and apparently chased him out of the tavern down Main Street. There’s a scene you’re not going to see put on the dollar bill!

Church Condos
6) Gentrification and Annapolis

As with many cities in the United States, many people left Annapolis for the suburbs in the second half of the 20th century. (Google “white flight” if you want to learn more about this sad phenomenon.) In the 21st century, urban living has become much more popular for a wide variety of reasons. (One of which is that suburbs are terrible and if you move your kids there, you’ll run the risk of raising uncultured zombies. I’m definitely an urban chauvinist. Yeah, I SAID IT.)

There are both plusses and minuses to this urban renewal, but one minus is definitely rising rents. There’s just not enough housing to accommodate people who want to move back to downtown Annapolis. This means that rising rents push out some longterm residents. It also means that people convert some strange spaces to housing. For example, this abandoned church above, which is actually…condos! I really don’t think I could sleep at night in a church. I’m only half Catholic, but that’s enough to make me feel too much Catholic guilt at the idea.

Mason's Lobster Roll
7) Mason’s Lobster Roll

After your jaunt around Annapolis concludes, you’re going to want to eat lunch. And this is Annapolis, so it’s an actual, literal crime to have a meal that doesn’t include seafood. Stop over at Mason’s Lobster Roll for a quick bite.

This is a casual local chain that only uses fresh Maine lobster on their buttery rolls. But you don’t need to take my word for how good they are; trust the endless lines outside. ( The lines move fast, so don’t worry if they stretch out into the street.) There might not be seating, so you can ask for your lobbie to go and take it out by the waterfront to eat.

Annapolis Harbor

I’m pretty sure this view could make any lobster taste even better.

William Paca House

One Day in Annapolis Itinerary

Afternoon: William Paca House

Annapolis’s main claim to fame is its number of historic homes. A guide told me that it has more colonial homes than any other city in America. And yet another claim to fame is that it is the only city in America that has the original houses of all its state’s signers of the Declaration of Independence. One of those signers was Mr. William Paca, and we’re in luck because today we’re going to visit The William Paca House.

The only way to visit the William Paca House is on a guided tour. The tour costs 10 dollars and you buy your tickets inside the house. However, for only 5 dollars, you can do a self-guided tour of the gardens of the William Paca House any time you want. I highly recommend the guided tour because the docents are so funny. Sadly, you can’t take photos inside the house. But I can share my photos of the gardens and my favorite…

three fun facts: william paca house

William Paca House Garden
1) Why Can You Tour the William Paca House?

Good question, Internet Stranger! The short answer, as usual, is money. The long answer is that the William Paca House eventually left the Paca family after Mr. Paca’s death. Like many historic homes, it became a hotel. But when the hotel was no longer successful, the William Paca House was slated for demolition. Fortunately, some historically minded Annapolitans decided to preserve the house. Now it is open for tours, so your admission helps keep the house from getting turned into a parking lot.

william paca house roses
2) Who Was William Paca?

William Paca, as I mentioned, was one of the signers of the Declaration of Independence from Maryland. He was one of the BMoC (Big Marylanders on Campus) back in Colonial days. After the Revolution, he became the governor of Maryland. I generally don’t trust anyone who is governor of Maryland, but that might be because I’ve seen too many episodes of The Wire. Our guide described Paca as “fat and handsome”. That’s not a way I’d like anyone to describe me, but then I am not a colonial man.

William Paca House back
3) Who lived in the William Paca House?

I’m going to let you off easy here, Internet Stranger, and not just say William Paca. Mr. Paca married a local wealthy woman named Mary Chew, so he and his wife were living large in the Paca House. The guide was sharp about pointing out the many signs of wealth in the house. Lots of these were not even recognizable as status symbols today. Did you know that apparently in colonial times, maps on walls were a sign of wealth? Brightly painted walls were too. I’m just going to paint my walls magenta and then cover them with olde tyme maps to see if that can convince people that I’m a very fabulous person.

When we arrived in the kitchen of the William Paca House, the guide reminded us that the Paca family enslaved several African-Americans who would have eaten in the kitchen. Though Maryland stayed with the Union during the Civil War, it was a slave state. Many of the beautiful historic homes in Annapolis were built and maintained using the labor of the enslaved.

Annapolis Harbor Evening

One Day in Annapolis Itinerary

Late Afternoon: Annapolis Harbor

My philosophy is that the hours between 5 and 7 PM should always be spent doing something relaxing. We’ve had a tough day of riding around in an E-cruiser, eating lobster, and looking at some fancy maps. We deserve a rest. So let’s look at the boats we can’t afford down in Annapolis Harbor.

kunta kinte alex haley memorial
24 Hour Treasure

Don’t miss the Kunta Kinte-Alex Haley memorial on Annapolis Harbor. It’s dedicated to Roots author Alex Haley and his ancestor Kunta Kinte. (People debate whether or not Kunta Kinte was really Haley’s ancestor. I know that, Internet Stranger, so please don’t send me nasty emails about it.) This sculpture shows Haley telling his story to three metal children. Visitors to the memorial are invited to remember the people who were enslaved and brought over to this country from Africa.

Alex Haley was not from Maryland, so you might ask why this memorial to him is here. Annapolis Harbor wasn’t always a picturesque stopping point for small yachts; it used to be a port for slave ships. Haley believed that Annapolis Harbor was where his ancestor was first brought in chains from Africa. So that’s why people chose this place for the memorial.

One Day in Annapolis Itinerary

Evening: Carrol’s Creek Cafe

After all that time staring at the water, I know I want to eat some seafood. Let’s end our One Day in Annapolis Itinerary with some of Annapolis’s freshest fish at the Carrol’s Creek Cafe. It’s technically in the Maritime Republic of Eastport, so you know their seafood is on point. We’ll be having three different kinds of “fruits de mer” in this one meal at least.

oysters carrol's creek cafe

For a starter, how about baked oysters covered with melted cheese and bacon? Now, this may well be the least kosher dish ever devised. It combines shellfish, pork, and mixing milk and meat. I can practically hear the ghost of my Jewish grandmother yelling at me for eating this.

I also think it would be a great way to get someone into oysters for the first time. They’re cooked, not raw, and the first thing you taste will be the melted cheese and bacon, and basically everybody likes the taste of those.

rockfish crab william paca house

24 Hour Treat: Rockfish

One of my favorite things about traveling is getting to find new kinds of food. That’s why I was so excited to see rockfish on the menu. I had never eaten a rockfish before, so I had to try it even if I was worried it would break my teeth. There’s no better place to try rockfish than Annapolis because it’s the state fish of Maryland.

You can find them all over the Chesapeake Bay, along with pirate impersonators. (Apparently you can also call rockfish striped bass? That’s very confusing. Pick a name and stick with it, fish!)

The fish was accompanied by a delicate crab risotto. I always like it when one type of seafood is paired with another type of seafood. They should call it Surf and Surf.

Annapolis Ice Cream

24 Hour Treat: Annapolis Ice Cream

Earlier that day, I’d been walking down Main Street, and I’d seen endless lines snaking outside of the Annapolis Ice Cream shop. “That must be good stuff if people will wait so long for it,” I thought. “Too bad I need to spend my afternoon trying to steal the expensive maps from the walls of the William Paca House instead!”

So I was delighted to see that Annapolis Ice Cream is on the menu at the Carrol’s Creek Cafe. What a perfect end to the One Day in Annapolis Itinerary! I got to sample their silken cinnamon flavor and I didn’t need to stand on line forever. Suck on that line-waiters!

That’s a Perfect One Day in Annapolis Itinerary!

What would you do with One Day in Annapolis Itinerary? How cute are the gardens at the William Paca House? And is the ghost of my Jewish grandmother really reading this blog? Please leave your thoughts below!

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 have a One Day in Annapolis Itinerary. If you have time for another One Day in Annapolis Itinerary, try this one!

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