I absolutely LOVED my visit to Annapolis, Maryland. There are sooooo many reasons why it’s a city that I want to bring my family back to. It’s a city that appeals to all of your senses. Beautiful historic buildings that provide architectural eye candy in every direction, a walkable downtown that makes it almost feel like a small town, a city rich in history and tradition, and a wonderful culinary scene located in close proximity to the water.
No visit to Maryland is every complete without a crab cake, just a warning that once you have experienced a crab cake in Maryland, it will wreck you when you eat them anywhere else.
You also can’t go wrong with a homemade pop tart at Iron Rooster, The Irish Reuben at Galway Bay Irish Restaurant and Pub, Seafood with a gorgeous view of the water at Carol’s Creek Cafe, and homemade ice cream at Annapolis Ice Cream Company (don’t forget to decorate a spoon while you are there.)
Most Memorable Crabcake
My favorite crab cake during my visit to Annapolis came from a visit to Chick and Ruth’s Delly for breakfast. You might notice that Delly is spelled incorrectly because the original owner spelled it phonetically. The timing for a crab cake was a bit odd but when you are told it is one of the best around you decide that you can eat crab cakes for breakfast and I’m so glad that I did!
Daily Pledge of Allegiance
Pictured above is Teddy Levitt. His parents started this deli in 1965 and he has been helping out since he was 8 years old. On Feb. 12, 1989, he invited customers to stand and say the pledge of allegiance with him and they have been joining him ever since at 8:30am weekdays and 9:30am on weekends.
They are known for the best crab cakes in the city. He is holding my breakfast that’s an 8 oz crab cake with jumbo lump crab with a homemade bun that I still dream about.
The restaurant is set up so you sit close and get to know your neighbors. You will also find pictures of well known public figures along the walls who have visited over the years. There is also a special booth inside the restaurant reserved for the Governor. A meal at Chick and Ruth’s has been a day after inauguration tradition for governors since 1969.
This restaurant takes pride in tradition and quality, natural ingredients. The history, personality of the owner, and the food make this a stop you MUST make a visit! Seriously, you need to experience this!
Beautiful historic buildings
Walk slowly so that you can truly take it all in. A few other points of interest would be the Maryland State House that dates back to 1772 and the William Paca House that’s a five-part Georgian mansion that dates back to the 1760’s with a gorgeous garden in the back.
The History Marker Program will give you more insight into the buildings you walk by.
Red: Georgian Architecture (1715-1800), Bronze: Georgian Buildings of National Importance (1730-1800), Blue: Federal Architecture (1784-1840), Green: Greek Revival Architecture (1820-1860), Purple: Victorian Era Architecture (1869-1901), Gray: 19th-20th Century Annapolis Vernacular Architecture (1837-1921) , Yellow: 20th Century Distinctive Architecture (1901-1938).
Check out the Historic Marker Program website for a walking tour for more buildings of interest.
You can’t help but get caught up in the sense of pride and awe as you step on the grounds of the United States Naval Academy. I HIGHLY recommend taking a guided tour through The Armel-Leftwich Visitor Center. The stories and history that you learn on the tour make the experience so much more meaningful.
I know that my kids will be especially interested in learning about the history and programs of the sport when they visit. Their football case has the game-winning ball from each time that Navy beat Army.
A visit to the United State Naval Academy will give you a greater appreciation and respect for those who choose to dedicate their lives to protecting our freedom.
Adventure on the Water
If you want a memorable and relaxing way to take in the scenery around Annapolis, I would suggest taking a 2-hour public sailing cruise on the 74-foot schooners, Woodwind or Woodwind II.
The miles that the Woodwind has sailed on the Chesapeake would equal over 2 times around the world. Woodwind II has some Hollywood bragging rights because it was used in the movie Wedding Crashers.
The cruise gives you another perspective of the United States Naval Academy, Annapolis Harbor, Chesapeake Bay, with Scenic views of Annapolis skyline and Severn River.
During the cruise, guests can volunteer to help raise the sails or take a photo opp in front of the steering wheel. I highly recommend an adventure on the water while you are in Annapolis.
A Scenic Winery 10 Minutes from Downtown
A visit to Great Frogs Winery is worth stepping away from downtown for a bit. The tasting room resides inside a former tobacco barn has been transformed on a farm that dates back to 1691.
Please note that tastings are by appointment only Fridays & Saturdays 1-5 pm – (410) 626-6193 Make sure that you also check their website for upcoming special events.
A Nautical Themed Night of Sleep
I absolutely LOVED the nautical theme at the Annapolis Waterfront Hotel. Find a great rate here. The location is perfect because you are walking distance from downtown shops and located right on the water. The room continues the nautical theme that is throughout the hotel.
You can catch a gorgeous sunrise on the dock located behind the hotel. I promise that it’s worth getting up early for.
This hotel has lots of intentional nautical details throughout the lobby, hallways, and room that didn’t go unnoticed, all the way down to the keycard.
I think that Annapolis has so much to offer for travelers and I cannot wait to come back again with my family.
Thanks again to Visit Annapolis for hosting my visit. You can find more information to plan your next visit from their website. This post contains an affiliate link.