The Ultimate Weekend Guide to Annapolis 2
Travel

The Ultimate Weekend Guide to Annapolis, Maryland

From the brick-paved streets to the waterfront shopping, Annapolis, Maryland is so charming and full of American history that it should be on your “Must Visit” list if you’re ever on the East Coast. And since Annapolis is less than an hour away from Washington, DC, visiting this waterfront town makes a perfect weekend getaway. We recently visited Annapolis for a quick babymoon before baby #2 comes and had an amazing time in just 2 days! Continue reading to get the ultimate guide on how to fill your weekend with what to do, eat, and stay while you’re in Annapolis, Maryland!

What to Do

Annapolis is such a walkable town that you can park your car once and spend the whole day discovering the charming streets and historical buildings all by foot. Here is a list of things to do in Annapolis, so you can pick and choose what entices you. 

Take a Trolley Tour

Taking a Discover Annapolis Trolley Tour is the best way to get to know the town of Annapolis, all within one hour! Then you can finetune the rest of your weekend itinerary depending on what interests you from the tour. In the one hour, you’ll learn all about the role Annapolis played in our country’s history while gazing at the most spectacular historic buildings. Did you know that Annapolis is home to the largest concentration of Georgian homes in America? Tickets are available online or on a walk-in basis and trolleys depart daily from April through October from the Visitor’s Center

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Stroll down Main Street

You cannot come to Annapolis and NOT take a stroll down Main Street. From unique boutique shops to delicious restaurants, you can spend hours walking up and down the brick-paved sidewalks. If you’re walking from Church Street, Main Street ends at City Dock, where you have an excellent view of Ego Alley and the parading boats. This is a great place to grab a meal outdoors, sunbathe on one of the benches on the dock, or even take a boat tour!

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Cruise the Chesapeake Bay

Speaking of City Dock, this is where you can hop on a boat tour to explore even more of Annapolis’ history from the beautiful Chesapeake Bay! Watermark has the perfect 40-minute narrated cruise that allows you to sit back and relax, enjoying the view and the wind in your hair. Check the website for the schedule, but in the spring and summer, tours depart every hour on the hour. 

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Naval Academy

As you’re walking through Annapolis, you may see groups of young men and women in uniform. This is because Annapolis is home to the United States Naval Academy (USNA), which was established in 1845! And did you know that the USNA is open to the public? If you’re a history buff, you can easily spend a few hours touring the USNA Museum or taking a guided tour to learn fun and unusual facts about midshipmen. Even better, the USNA is within walking distance to Main Street (less than 0.5 mile!), so it’s easy to visit one of Annapolis’ longest standing institutions. 

The Ultimate Weekend Guide to Annapolis

William Paca House

Another historic landmark that calls Annapolis home is the William Paca house. This Georgian mansion was built by William Paca in the 1760s, who was one of Maryland’s four signers of the Declaration of Independence and the state’s third governor. Step away from the bustling city and retreat to the William Paca house and gardens, which are sprawled over two acres. On a guided hour tour, you’ll get an insider’s look at how the 19th century elite lived, from the plush furnishings to the historic paintings. After the tour, take a stroll in the immaculate gardens, where butterflies flutter from flower to flower and the tall hedges make it hard to believe that you are actually in the middle of Annapolis!

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Maryland State House

The Maryland State House is definitely worth a visit while you’re in Annapolis. Just steps from Main Street, the Maryland State House is the oldest state capitol in continuous legislative use in the US and is even the ONLY state house ever to have served as the nation’s capitol! Thus, it was in the Old Senate Chamber that General George Washington came before Congress in December 1783 to resign his commission as commander-in-chief of the Continental Army. Just weeks later, Congress ratified the Treaty of Paris in January 1784, formally ending the Revolutionary War! You can just feel the amount of important American history that took place at the Maryland State House as your steps echo through the marble-filled hallways. 

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Great Frogs Winery

While the Great Frogs Winery is not quite within walking distance of downtown Annapolis, it is still a short drive away and a great escape for a few hours. Great Frogs Winery focuses on small batch production of their artisan crafted wines. All tasting experiences are by reservation only, so be sure to check the website to book. Reservations allow for a seated tasting experience in a small and intimate setting. Spending a few hours at Great Frogs Winery is a wonderful way to add a slower-paced activity in an otherwise fun-filled itinerary! 

Where to Eat

While there are tons of unique options for places to eat in Annapolis, here are some MUST VISIT places that are iconic to the charming city. 

Miss Shirley’s

One of your weekend days must absolutely start with a breakfast or brunch date at Miss Shirley’s. Be forewarned – there will be a line as they don’t take reservations. But trust me, that line is worth it. Less than a mile’s walk from Main Street, Miss Shirley’s serves traditional southern flare for breakfast, brunch, and lunch while also using local ingredients from the Chespeake Bay region of Maryland. They were even featured on Food Network’s Diners, Drive-Ins, and Dives! We had one of their specials of the day – a stack of pancakes stuffed with pulled pork and cheese ????. We also shared Shirley’s Affair with Oscar, which is a 5 oz. Black Angus Filet topped with jumbo lump crab meat and hollandaise and voted Best Breakfast Dish in Maryland by Food Network Magazine! Whatever you choose at Miss Shirley’s, you can’t go wrong. And you’ll be back again to try something different. 🙂

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Iron Rooster

Iron Rooster is known for its breakfast. So much so that they serve it all day! Breakfast fare includes pancakes, waffles, omelets, and benedicts. But they also have specialty items, such as breakfast bowls and fried chicken. We had the shrimp and grits and fried chicken and pancakes! I would highly recommend sharing Iron Rooster’s signature Roostart, which is their homemade version of a Pop-Tart! They are made fresh daily and the flavors do vary by day/season. We would probably come back just for the Roostart! 

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Annapolis Ice Cream Co

While you’re strolling on Main Street, make sure to stop at Annapolis Ice Cream Co for some premium, homemade ice cream! They are the only place in Annapolis where ice cream is made on-site daily! You’ll have a hard time deciding on what to get as there are over 40 flavors that they rotate daily. Good thing that you can sample the flavors first!

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Carrol’s Creek Cafe

Eating seafood with a water view is a quintessential Annapolis experience and there’s no better place to do that than at Carrol’s Creek Cafe. Just a 5-minute drive from Main Street, Carrol’s Creek Cafe offers traditional American dining and seafood that takes advantage of the abundance of the nearby region – both land and water. We opted to get seafood to go along with our panoramic view of the water. We had the grilled swordfish and surf n’ surf with delicious lobster tail and a jumbo crab cake. Watching the sunset while finishing off our meal with the coffee and donuts bread pudding was absolutely divine. Whether you are celebrating a special occasion or looking to eat a delicious meal after touring Annapolis, you can’t beat the view or food at Carrol’s Creek Cafe!

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Where to Stay

The Westin Annapolis

Less than a 15-minute walk from the heart of downtown Annapolis, the Westin Annapolis offers luxurious and upscale accommodations while still being close to all the attractions. After a full day of sightseeing, retreat to your modern room that is complete with heavenly bedding and a spa-like bathroom that even has a rain shower head! You can even continue your healthy habits while on vacation with the Westin’s fitness center and indoor pool!

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The Academy Bed and Breakfast

Right in the heart of historic downtown Annapolis, The Academy Bed and Breakfast is the epitome of the charm and charisma that Annapolis has to offer. The spacious master suites have been renovated with elegant furnishings and include oversized spa baths. With a stay here, you are not only at home away from home, you are literally steps from all of the action on Main Street, museums, and the Naval Academy!

Annapolis Waterfront Hotel

Annapolis Waterfront Hotel is Annapolis’ only true waterfront hotel (hence the name! :)). This hotel offers breathtaking views of the Annapolis Harbor and the Chesapeake Bay and a unique experience as you are steps away from attractions, shopping, dining, and nightlife. The 150 guestrooms are spacious and decorated with a sea-inspired palette and many of the waterfront rooms have private balconies! You’ll get a true Annapolis experience with a stay at the Annapolis Waterfront Hotel. 

See all the amazing things you can do and see in Annapolis, Maryland?! With this guide, there will be no shortage of small-town charm as you walk your way through the waterfront shops and small alleyways lined with colorful houses. Have you been to Annapolis, Maryland before? What would you do and see if you were to spend a weekend in Annapolis? I would love to hear your thoughts so comment below!

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3 Comments

  1. Thank you for visiting Annapolis! We are glad you enjoyed your stay with many of our awesome hospitality partners. For more information on visiting the U.S. Naval Academy visit: http://www.usnabsd.com/for-visitors. We are open 7 days a week for tours, a great theater experience and historical exhibits in our Visitor Center. Great shopping at our gift shop as well!

    1. Hi Maureen, thank you for reading! I certainly hope you can visit Annapolis one day. Such a great small town with tons of history 🙂

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