Discover Why You Will Fall in Love With Annapolis

I absolutely LOVED my visit to Annapolis, Maryland.

There are sooo 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.

Iron Rooster Annapolis Maryland

Great food in Annapolis

No visit to Maryland is ever complete without a crab cake.

Once you’ve experienced a crab cake in Maryland, it will wreck you when you eat one anywhere else.

You also can’t go wrong with a homemade pop tart at Iron Rooster.

Galway Bay Irish Restaurant and Pub Annapolis Maryland

Enjoy the Irish Reuben at Galway Bay Irish Restaurant and Pub.

Carol's Creek Cafe Annapolis Maryland
Annapolis Ice Cream Company e1478351460805

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.)

Chick and Ruth's Delly Annapolis Maryland

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!

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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.

They have been joining him at 8:30am on weekdays and 9:30am on weekends ever since.

They are known for the best crab cakes in the city. He is holding my breakfast which’s an 8 oz crab cake with jumbo lump crab. It’s on a homemade bun that I still dream about.

Chick and Ruth's Delly Annapolis Maryland

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. 

Chick and Ruth's Delly Annapolis Maryland

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!

Annapolis Maryland

Beautiful historic buildings in Annapolis

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.

The William Paca House is a five-part Georgian mansion that dates back to the 1760s with a gorgeous garden in the back.

Downtown historic Annapolis Maryland

The History Marker Program will give you more insight into the buildings you walk by.

Downtown historic Annapolis Maryland

Colors for the Historic Market Program in Annapolis

  • 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).
Downtown historic Annapolis Maryland
Downtown historic Annapolis Maryland

Check out the Historic Marker Program website for a walking tour for more buildings of interest.

United States Naval Academy Annapolis Maryland

Military Tradition in Annapolis

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.

United States Naval Academy Annapolis Maryland

A few of the tour highlights include Lejeune Hall, Bancroft Hall, Tecumseh Court, Herndon Monument, Main Chapel (when open), and the Crypt of John Paul Jones, Revolutionary War hero.

United States Naval Academy Annapolis Maryland

I know that my kids will be especially interested in learning about the history and programs of the sport when they visit.

United States Naval Academy Annapolis Maryland

Their football case has the game-winning ball from each time that Navy beat Army.

United States Naval Academy Annapolis Maryland

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.

Woodwind schooner Annapolis Maryland

Adventure on the Chesapeake Bay

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

Woodwind schooner Annapolis Maryland

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.

Woodwind schooner Annapolis Maryland

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.

Woodwind schooner Annapolis Maryland

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.

Great Frogs Winery Annapolis Maryland

A Scenic Winery 10 Minutes from Downtown Annapolis

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.

Great Frogs Winery Annapolis Maryland
Great Frogs Winery Annapolis Maryland

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.

Great Frogs Winery Annapolis Maryland

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A Nautical Themed Night of Sleep

I absolutely LOVED the nautical theme at the Annapolis Waterfront Hotel. Find a great rate here.

Annapolis Waterfront Hotel

The location is perfect because you are within 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.

Annapolis Waterfront Hotel

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.

Discover Why You Will Fall in Love With Annapolis

4 thoughts on “Discover Why You Will Fall in Love With Annapolis”

  1. We just loved Annapolis. We went there on a spontaneous weekend with the family and enjoyed a ton of live music too. What was great is many allowed the kids!

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