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1 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

One Day in Annapolis Itinerary

Where to Stay

When I enjoy a one day in Annapolis itinerary, I recommend staying at the Scotlaur Bed and Breakfast. It has a perfect location within walking distance of the main attractions in Annapolis, like the harbor, the William Paca House, and even the Maritime Republic of Eastport. There’s also free wifi, which is important if you need to work on the road, like I do.

And speaking of delicious, the breakfast is excellent as well. In fact, I would go so far as to say they really put the breakfast in the phrase bed and breakfast. 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! Annapolis is small, but it is quite popular with tourists, so there’s plenty of options for hotels and bed and breakfasts.

1 Perfect One Day in Annapolis Itinerary 1

One Day in Annapolis Itinerary

What to Pack

  • An excellent small cell charger so you can keep taking pictures all during your one day in Annapolis itinerary.
  • The best full-length guide to the state of Maryland. That means you’ll be able to use it in Baltimore and the rest of Maryland
  • Do not pack a tri-cornered hat. Just steal one from a guide in Annapolis.
  • My book Get Lost, that I wrote myself with all my best travel tips. This book will show you exactly how solo travel can take your life from BLAH to amazing!
  • Want to learn how I saved enough money to travel 16 weeks a year? Check out my top secret How to Afford Travel digital system.
  • I always travel with travel insurance from World Nomads. You never know when something might go wrong, especially in this day and age. But with travel insurance, you’re protected even if you’re attacked by the British troops during your one day in Annapolis itinerary.
one day in annapolis itinerary

One Day in Annapolis Itinerary

Morning: Explore Annapolis

Of course, we could take on our one day in Annapolis itinerary by ourselves. But wouldn’t it be easier to have an expert guide take us around instead? That’s why I suggest booking the Heart of Annapolis tour with Urban Eventours.

The tour leaves from the Annapolis Visitor Center, located right in the center of town. Your friendly local guide will take you around in an adorable e-cruiser, so your feet won’t explode from walking too much. And on top of that, your brain will be stuffed with fun facts!

I don’t want to spoil all of the tour, so I’m just going to share with you…

approximately top 5: One Day in Annapolis Itinerary 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.

One Day in Annapolis Itinerary
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.)

One Day in Annapolis Itinerary
3) Explore Maritime Eastport

After Saint Anne’s Church, we crossed the 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!

Your guide will surely tell you about the annual tug-of-war competition between Eastport and Annapolis that takes place once a year. (Yes, that means that the rope is so long that it goes from the Eastport side of the harbor to the Annapolis side of the harbor.) If you’re able to visit Annapolis in November, don’t miss it. It looks like a hoot.

One Day in Annapolis Itinerary
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.

one day in annapolis itinerary
5) St. Mary’s Church

We’ve seen the Anglican POV earlier on this tour, so now we get to see the Catholic perspective at St. Mary’s. The loveliest thing about the interior of this church is the ceiling, which was painted to look like the sky.

But those aren’t just a random collection of stars that you see above you! The sky was actually painted to exactly replicate the sky at the moment that the church was consecrated. How symbolic! And how pleasant that Anglicans and Catholics can live together in Maryland without conflict once again.

one day in annapolis itinerary
6) St. John’s College

This lovely St. John’s campus isn’t the most famous college in America, but it is one of the most historic. In fact, it’s the third oldest college in the United States, after Harvard and William and Mary. The school follows a Great Books curriculum, which means that the students don’t pursue individual majors. Instead, they read and discuss the classics.

We saw the other famous college in Annapolis, the Naval Academy, on our previous Annapolis itinerary, so it’s only fair to give St. John’s equal time. St. John’s and the Naval Academy are friendly rivals, and they even compete in a massive croquet match once a year. Which would be more fun: seeing the giant tug-of-war or the Naval croquet match? I suggest seeing both and then reporting back to me about it!

one day in annapolis itinerary
7) Sofi’s Crepes

After your jaunt around Annapolis concludes, you’re going to want to eat lunch. I suggest asking your guide for a good suggestion for a place to eat. He or she will even drop you off at the restaurant if it’s not too far away. That’s how I ended up stopping over at Sofi’s Crepes for a quick bite.

Sofi’s has both sweet and savory crepes, but I chose their most popular savory crepe, which is the Kevin Bacon. This decadent deliciousness comes with Cheddar, tomato, turkey, 1000 Island Dressing, and of course, bacon. (I did not count the bacon, so I can’t confirm whether or not it was six degrees worth of bacon.) This is the perfect lunch to keep you full until our giant dinner.

one day in annapolis itinerary

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 12 dollars and you buy your tickets inside the house or online right here. 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. For the purposes of this itinerary, I suggest taking the 1:30 PM tour. 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

one day in annapolis itinerary
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 eventually became a classy hotel.

But classy doesn’t always bring in the cash, and 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.

one day in annapolis itinerary
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.

one day in annapolis itinerary
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. All of the beautiful historic homes in Annapolis that I visited were built and maintained using the labor of the enslaved.

The docents at all these homes are working hard to learn more about the lives of the enslaved people so that their stories are given as much attention as their enslavers.

one day in annapolis itinerary

One Day in Annapolis Itinerary

Late Afternoon: Annapolis Harbor

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.

one day in annapolis itinerary
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 above 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 four different kinds of “fruits de mer” in this one meal at least.

one day in annapolis itinerary

For a starter, how about the famous scallop appetizer? In fact, it’s so famous, my tour guide told me that I needed to order this dish. It’s extremely rich with shrimp, cream sauce, lump crab, and prosciutto, but it is worth every bite.
There’s also tons of crisp-ness (Crisposity? Crispin Glover? Not sure what the right word is here.) because the scallop is cooked inside a phyllo dough and topped with a whole bunch of crispies. But never fear! Despite the cream and carbs, this dish is definitely good for you because of the spinach. That’s just science.

one day in annapolis itinerary

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.

1 Perfect One Day in Annapolis Itinerary 2

24 Hour Treat: Donut Bread Pudding

After all that cream and fish and decadence, do you still have room for dessert? Of course you do! So let’s dive right into decadence with some donut bread pudding along with coffee ice cream and Maker’s Mark caramel sauce.

I thought it was a pretty clever concept to combine donuts with coffee as if we were having a kind of breakfast and dessert rolled into one. After all, everyone knows that breakfast and dessert are the two best meals, so what could be better than Breakfast-Dessert? This was a perfect end to the one day in Annapolis itinerary.

one day in annapolis itinerary

One Day in Annapolis Itinerary

How to Get There

By Car: This is the easiest way to get to your one day in Annapolis itinerary, if you are coming from somewhere else on the East Coast in the United States. There’s not a ton of regular public transportation that goes to Annapolis, and the city has no airport. 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.) You can, of course, rent a car at the Baltimore airport.

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 your one day in Annapolis itinerary 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 one day in Annapolis itinerary.

one day in annapolis itinerary

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? Email me at [email protected] 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 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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