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Experience Historic Annapolis: A Day Trip Itinerary

Updated: Apr 24, 2023

It was September 2018 when I visited Annapolis, Maryland. The tropical storm Florence was moving to the East Coast creating havoc, and I had flown in for a work conference. Knowing that I would be in this capital city, I had booked an extra day to see the state house and other historical places.

Florence had made the east coast look even drearier. It rained randomly, and portions of the roads and alleys were flooded. But I still thought this was one of the most charming areas I'd ever seen with Annapolis's cobblestone streets and quaint houses. Granted, I stayed mostly in the historic district, but that's the best place to be in the city anyway as a tourist.

There are a couple facts that make this city so appealing: 1) Annapolis is located in Chesapeake Bay, so you're right on the water; 2) Almost every important activity is in walking distance; 3) You only need a day (a weekend max) to see all the important sights; 4) There are some really cool sights.

This makes Annapolis the perfect day trip destination, whether you're flying to it or driving through it. So, add it to your east coast road trip or book the necessary transportation to get you there, and check out this itinerary for your arrival to this picturesque little city.

What You'll Find In This Post:


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Your Annapolis Itinerary

It's safe to say that if you're not into historical locations or museums, this city might not be for you. The best things to do in Annapolis are learning about its history (because it goes way back) and enjoying the bay (its scene and food). But even if you're not the biggest history buff, keep reading. There might be something in this itinerary that really intrigues you.

Learn About the Maryland State House

Most capital buildings might not seem very interesting, but let me share a few facts about the Maryland State House that might get you excited about visiting it.

  • It was the capitol of the U.S. from November 1783 - August 1784.

  • It's the oldest state house in America in continuous legislative use (completed in 1779).

  • It was America's first peacetime capitol.

  • It was the location of George Washington's resignation speech, which was the first stepping stone in establishing the U.S. as a republic, not a monarchy. (Cue "One Last Time" from Hamilton.)

When you step inside the Maryland State House, you're stepping into history, and you can learn more about all of these facts above by walking through the capital's rooms/museums. You'll find everything from historical documents and portraits to information about the architectural elements of the building.

The Maryland State House opens at 8:30 a.m., making it the perfect first stop.

Tour the William Paca House & Garden

The William Paca House is a 5-part Georgian mansion with a beautiful 2-acre garden. William Paca, one of Maryland's four signers of the Declaration of Independence, built this house in the1760s. It was later restored in 1965. The house is now considered a National Historic Landmark and one of the finest 18th-century homes in the country.

During your visit, you can go on a guided tour of the house and learn about its history, William Paca, period furnishings and paintings. The garden can also be included in this tour, or you can take a self-guided stroll. I enjoyed seeing the various rooms in the house, the tour guide was informative and the garden was a gorgeous place to spend the early afternoon.

This landmark is open Monday - Saturday from 10 a.m. to 5 p.m. and Sunday from 11 a.m. to 5 p.m. Tours are offered daily every half hour starting at 10:30 or 11:30 a.m.; the final tour is at 3:30 p.m. The last entry into the garden is at 4:30 p.m.

Admission is $12 for adults and $7 for children (ages 3-17).

Grab a Lobster Roll for Lunch

Yes, I know Maryland isn't the prime destination for lobster rolls. And yes, I also know that Mason's Famous Lobster Rolls is a chain, but for a first-time lobster roll eater, I thought it was yummy! The restaurant prides itself in being authentic — aka getting its lobsters from Maine — and the food even tasted pretty fresh to me.

If you're not into lobster rolls or are simply feeling something else for lunch, you have many other options, too. And plenty of walkable ones.

Explore the U.S. Naval Academy

The academy has been training men and women for the U.S. Navy and Marine Corps since 1845. Because of this, it has a lot of history to share, and there are several ways you can experience it.

Start with a visit to the Armel-Leftwich Visitor Center where you can see a short film and get tickets for a 1-hour walking or driving campus tour (held from 10 a.m. to 2 p.m.) with a certified guide. Or get information at the center before going on a self-guided campus tour. Some places to note include the Naval Academy Chapel and Navy-Marine Corps Memorial Stadium.

The U.S. Naval Academy museum, which showcases artifacts and historical information, is also a must. And before you leave, check out the gift shop in case anything catches your eye.

The campus is open Monday - Sunday from 9 a.m. to 4/5 p.m., but keep in mind that the museum is closed on Tuesdays. Also, all visitors over the age of 18 are required to show a valid ID.

Shop on Main Street

I've saved the shopping portion of this day trip for last because most of the other sight-seeing activities are over by 5 p.m. or before. The shops down main street are open until 6 p.m. or later almost every day, so you'll have plenty of time to find those souvenirs you were hoping for, gifts for your family and friends or just items you love.

I'm not a shopper but enjoyed walking down this Main Street and peering into all the stores. There are a wide variety of small businesses and boutiques selling clothing, specialty foods, home décor, etc. Many are local, too, which is always a bonus.

You can also check out the galleries and other artistic shops as you go. I just recommend saving your final meal of the day for a restaurant overlooking the bay.

Eat Dinner on the Water

In my opinion, eating a nice dinner on an outdoor patio overlooking the bay is a must! It was one of the most relaxing evenings I had enjoyed in a long time as I listened to the water slapping against the boats docked, watched the sun go down and ate incredible seafood.

I wish I could remember which restaurant I ate at specifically. (Was it Carrol's Creek, The Choptank or O'Leary's Seafood? Who knows!) Whichever restaurant I went to, the food there was delicious, so check out your waterfront dining options.

Stay at the Annapolis Waterfront Hotel

If you plan on staying in Annapolis for the night and are looking to be pampered at a nice hotel, don't go far! The Waterfront Hotel is in a prime location overlooking the marina and is probably right next to wherever you've just eaten. You can get a room with a view of the city or one with a panoramic window or balcony facing the bay, which is perfect for watching the sunset in the morning before leaving Annapolis to go on your next adventure.

Extra Sights Around The City

As you walk through Annapolis, there are a few other tourist sights that might catch your attention. Stop and take a look at them! They're important, too ... just not major enough to pass the time like the other activities and more spread out.

Memorials and Monuments

Be on the lookout for various statues (memorials and monuments) around Annapolis. Some of the most well-known ones include the Kunta Kinte-Alex Haley Memorial (shown in the photo above), Thurgood Marshall Memorial, Baron Johann De Kalb statue, and Maryland World War II Memorial.

You'll find these statues all over the city, but many are also in "pockets," such as near the state house or inside the U.S. Naval Academy. (The academy even has a statue of its mascot: Bill, the goat.)

Use this online guide, which shows the location of most of the sculptures, as you walk around the city.

Building Markers

Through the historic Annapolis Marker Program, more than 280 properties in the city have markers on them highlighting preserved buildings. The markers are color-coded, and each color represents a different architectural period and design.

Red: Georgian (1700s-1820s)

Blue: Federal (1780s-1840s)

Green: Greek Revival (1820s-1860s)

Purple: Victorian (1850s-1910s)

Gray: Annapolis Vernacular (1830s-1930s)

Yellow: 20th Century Distinctive (1900s-1940s)

You should be able to find a pamphlet with more information about this program and specific buildings to be on the lookout for during your day in Annapolis at the visitor's center. You can also head to this link for some additional information about the architectural periods.


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