How To Spend a Day in Charming Annapolis

July 9, 2019

bird sculpture in Annapolis, Maryland

Last Updated on March 13, 2020 by Candy Wafford

Quaint, charming, delightful are all words that perfectly describe Annapolis.  If you haven’t been, you need to go! It doesn’t get as much attention as it’s busier neighbors Washington D.C. and Baltimore but it should because it is easy to visit and there is so much to do in Annapolis.

Before making it to Annapolis, we spent a frustrating morning in Washington D.C.  Anxious to get out of congested D.C. and onto the real reason for our trip which was to meet new family members, we had time to kill.  I had been assured that I would love Annapolis and boy did I. It was like a gentle hug after our morning in D.C. Charming is an over-used phrase but it’s the perfect description for this gem of a city.

I would have been perfectly content to spend a day in Annapolis just strolling it’s cobblestone streets, eating ice cream, and popping in and out of shops. All of which we did, but there are so many activities in Annapolis from fun things for kids to do and more.

What to Do in Annapolis – Visit the Visitor’s Center

Lately, I find I’m really appreciating the value of a visit to visitor’s centers.  They are a great place to not only get information about a place but also to use the facilities, cool off or warm-up and grab a drink.  Often the employees love being ambassadors for their town and can give you some great tips on what to do. 

Visitor's Center in Annapolis, Maryland

The Annapolis Visitor’s Center was all of these things and more.  There is an easy to use parking garage adjacent to the center that was perfect for leaving the car while we explored Annapolis on foot.  I also enjoyed the sculpture and historic information in the gardens around the building.

You can also sign up for tours in Annapolis and they had some really interesting ones available but our schedule didn’t allow us to join any of them. We’ve already decided we want to do a tour next time we visit Annapolis.

Eat Ice Cream

Ice cream maybe my favorite thing in the world and I always seek it out when traveling.  I especially like locally owned ice cream shops like Annapolis Ice Cream where there are unique flavors and the ice cream is made in-house.

Annapolis Ice Cream sign

The ice cream isn’t visible in the cases which I found to be kind of weird.  I couldn’t see the ice cream, but I still had trouble deciding which flavors to select from the 20+ options available.  I went with Strawberry Nutella and Black Raspberry.  So, so good! 

What to Do in Annapolis – Eat at Chick & Ruth’s Delly

I had Chick & Ruth’s Delly down on my list of possible restaurants to try and we ended up having lunch there.  It’s quirky, to say the least!  We weren’t there for the daily pledge of allegiance which happens at 8:30 AM Mon-Fri and at 9:30 AM on Saturday and Sunday. 

Crab Cake Sandwich and Crab Eggs Benedict at Chick & Ruth's Delly in Annapolis, Maryland
Crab Cake Sandwich and Crab Eggs Benedict

This is an old-school restaurant! Like it hasn’t been updated, ever. But I love places like this! Being in Maryland, we opted for dishes with crab and they were OK.  Next trip, I would order more traditional diner grub like one of the many sandwiches they offered.

Visit the United States Naval Academy

I didn’t visit the Yard as it is referred to but my husband received a personal tour from his brother, a graduate of the Naval Academy. He seemed most impressed that 4,000 cadets eat their meals at the same time.

Guided tours are available of the historic campus are available.

What to Do in Annapolis – Walk the Waterfront

waterfront in Annapolis, Maryland

Located on the Chesapeake Bay, the waterfront is one of the main attractions of this colonial city.  Walking along the waterfront and seeing all the boats and families enjoying the scenery is the type of simple pleasure only a town like Annapolis can offer. 

Get on the Water

boats in front of restaurant in Arnold, Maryland
The Parking Lot for The Point

Known as The Sailing Capital of the US, Annapolis offers any time of water activity you can imagine from sailing, fishing, and kayaking. Our friends live in the area and we were able to take their sailboat out on the water for a while.  Is there a better way to see a place than with the sun on your face and breeze blowing through your hair as you glide through the water?   


Hippie Element Shop in Annapolis, Maryland
Hippie Element was a super fun shop

So. Many. Cute. Shops. Just one right after the other along the main street in Annapolis. I especially like locally owned shops that feature local products and there are many of these in Annapolis. There are also national brand storefronts including Alex & Ani and Sperry. This is also an artsy town and there are plenty of sea-themed souvenirs available.

What to Do in Annapolis – Take in the History

Annapolis was established in 1696 and is the capital of Maryland.  My husband is a history buff and I wish we had taken a tour to learn more about Annapolis history and the role this city played in our country’s history. 

Capital Building in Annapolis, Maryland
Sneaking a peek of the Capital Building

In addition to the U.S. Naval Academy and the State Capital Building, you can also visit the homes of the four Maryland signers of the Declaration of Independence. The city is a historical attraction itself and oozes history from every crack in it’s cobblestone streets. We enjoyed admiring the colorful row houses on Pinkney Street.

colorful row houses on Pinkney Street in historic Annapolis
Row Houses on Pinkney Street

Eat at The Point

Cheating a little here, because The Point Crab House & Grill is actually located in Arnold a few miles away. But it’s close enough and worthy enough of your time to make a small detour.

The Point Crab House Restaurant in Arnold, Maryland
The Point

We sailed to the restaurant and then had one of the best meals I’ve had in a while. We started with the mussels and I couldn’t stay out of them. They were so fresh and the garlic bread was the perfect vessel to sop up the cooking broth. But the crab cakes! Oh my goodness! I think it was the slowest I’ve ever seen my husband eat. His crab cake sandwich was so good he didn’t want the experience to end!

Final Thoughts

We absolutely loved Annapolis. It has the unique ability to be a bustling but calming at the same time. Combine its charm (there’s that word again) and with many restaurants, shops and activities to choose from visitors will fall in love with Annapolis.

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More about Candy Wafford

Candy Wafford is a US-based travel blogger and while she travels frequently for her job, she is happiest when traveling for pleasure. Preferably strolling along a cobblestoned street with an ice cream cone in her hand.

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