5 things you must do on a day trip to Annapolis

I was visiting my best friend in the Rockville area of Maryland to celebrate her daughters Bat Mitzvah and I had a free day on Sunday. Since Annapolis was only about 1 hr drive away I decided it would make for a perfect day trip.  Actually, Annapolis makes a perfect getaway for anyone living or visiting Baltimore, MD, Washington D.C., Philadelphia or Richmond, VA.

Annapolis is a beautiful historic waterfront city that once enjoyed the spotlight as the Capital of the United States. Today, Annapolis it is the Capital of Maryland and the home of the United States Naval Academy. It also has beautiful old streets filled with boutiques, restaurants and cafes as well as incredible views of the Chesapeake Bay.  Read along for my list of must do’s on a day trip to charming Annapolis.

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1.Get out on the water

Annapolis is considered the sailing Capital of the US therefore you should really consider at least one water activity.  There is something for every budget and fitness level. You could charter a private sail boat or try your hand at fishing and crabbing. Or take a leisurely 40 min or 90 min cruise with Watermark cruises.  If you rather get some exercise you can always rent a kayak or even learn to sail at one of the sailing schools. Schooner Woodwind has great sunset cruises. And for an inexpensive way to get on the water ride the water taxi.


Inside the Naval Academy

2.See the historic sites

Naval Academy – Founded in 1845 the U.S. Naval Academy is a prominent institution in Annapolis and a must visit while in town. It is a highly secure area that requires identification to be let in. It almost feels like walking though airport security.

But once inside there are 338 acres of history to explore. Public guided tours are available daily from the visitor center. or you can walk the grounds on your own.  It can get crowded and I recommend you arrive early. But this is a must so don’t leave Annapolis without seeing the Naval Academy.

William Paca House –  Enjoy touring the Georgian Mansion of one of the four signers of the Declaration of Independence. Beautifully restored with period furniture and meticulously maintained gardens.

Maryland State House

Maryland State House –  Did you know that no nails were used in its construction and that it is the oldest state capital still in continuous legislative use? It is also the place where George Washington came before Congress to resign his commission as commander-in-chief of the Continental Army.

St Annes Church –  A beautiful Romanesque Catholic Church with gorgeous stained glass windows. 

Kunta-Kinte Alex Haley Memorial

Kunta Kinte-Alex Haley Memorial –  Located on City Dock this memorial portrays the triumph of the man spirit in very difficult times. As well as national racial reconciliation and healing. A great place to sit and enjoy a cup of coffee while talking to locals and people watching.

Banneker-Douglas Museum –  For African American heritage and history in Maryland this is the perfect museum to visit.


3.Get some good food

With the Chesapeake Bay nearby it is no wonder that seafood abounds. You will find plenty of Maryland’s famous crab cakes as well as other types of fresh seafood like fish, shrimp, scallops, oysters and more.  A few places you should consider:

For Seafood: Boat Yard Bar and Grill, Carol’s Creek Café, Dock Street Bar and Grill, Sailor Oyster Bar.  And my favorite for fresh local oysters and crabs at a great price Wild Country Seafood.

For Coffee: Bean Rush Cafe, Ceremony Coffee and City Dock Coffee.

For breakfast: The Iron Rooster has great southern comfort food. Or you can try a local favorite Miss Shirley’s Cafe.

Don’t forget dessert: Annapolis Ice Cream Factory is the best. With over 36 flavors made fresh in house every day it will be hard to pick just one.  Portions are large so come hungry.


Main Street – Annapolis

4.Go shopping

Downtown Annapolis has lots of charm and is full of unique boutiques. You can find a wide selection of goods. Lots of preppy sailing chic styles, teas, oils, and plenty of other souvenirs.  The best streets to roan for shopping are Maryland Ave and Main Street.


5.Catch a sunrise and/or Sunset

Come in early or stay late and enjoy a beautiful sunrise or sunset from the dock or from the water. Take time to sit and enjoy the site of the start or end of a day.


B&B in Annapolis

Where to Stay

A day trip is perfect. But if you are looking to stay overnight or for a weekend, I would suggest either the Lowes Annapolis or the Marriott waterfront hotel. If you prefer a more homey feel there are plenty of B&B’s to chose from.

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Have you been to Annapolis? Feel free to share any of your favorites activities, restaurants or hotels.  I will be happy to hear about your suggestions.

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  1. What a pretty city! I never realized Annapolis was the sailing capital of the U.S. I’d love to check out the William Paca house. I really love visiting historical homes that have been maintained and/or restored. You can learn so much about the daily life back then just from seeing how people lived.

    1. It is the perfect place for sailing and the history is everywhere so if you enjoy that aspect you will love this town.

  2. Another gem. Thank you Joella for loving to travel and sharing your experiences. I’ve never been to Annapolis.

  3. Annapolis looks lovely and I could easily make my perfect day out of the things to do here: Kayaking – seafood and sunsets. In that order!

  4. I have not been to this area, it looks great! You really can’t go wrong with crab cakes and history, love the Kunta-Kinte Alex Haley Memorial

  5. Thanks for the great guide – I would love to visit Annapolis, and I totally agree that with a town by the water you can’t miss at least one water activity – I’ve heard incredible things about sailing on Chesapeake Bay. And then of course after a day on the water you shouldn’t miss out on an evening / lunch of seafood – I would love to try Maryland’s famous crab cakes!

    1. Sailing is the perfect activity in Annapolis. And the food is to die for. Hope you go and enjoy the beautiful town.

  6. I’d love to visit Annapolis. We were just in the area last month, but we didn’t have time for Annapolis. Maybe next time. We live in Missouri, so our time is always limited. We did Williamsburg, Yorktown, and Jamestown. We also did Virginia Beach and Norfolk. When we get up there again, we’ll have to check out Annapolis.

    1. You were able to do so much and visit amazing destinations. There is so much to see in the US and I know how hard it is to try and see it all. Hopefully net time you are in the area you will have the opportunity to enjoy Annapolis.

  7. Omg would love to go on one of the watermark cruises! Going out on the water is one of the most fun and unique ways to explore different places so I’m glad this is an option!

    1. So many water options here. Being out in the Chesapeake is a great experience and something everyone should do if visiting Annapolis. There is certainly an option for every budget and being on the water should not be missed. It is a great way to see the city as well.

  8. Annapolis is indeed a revelation. The place looks so charming and has some great historic sites too. The waterfront is really enchanting. I am sure the place holds the promise of a great experience.

    1. It was a great day trip and I am very glad I took the time to explore. There is certainly something for everyone and plenty of charm and history.

  9. I am not American and therefore I have never heard of this place ha ha. However, I will need to add it to the bucket list, especially if I can kayak at sunset :-)!

    1. There is so much to do on the water here. I had never heard of this place either until I did some research on things to do for a day while staying in Maryland. Glad you have discovered another place to visit.

  10. This is a great first timer’s guide to Annapolis! It’s really easy to follow and has good stuff to do. I think my first stop would be the food. It looks so good, and I love seafood.

    1. There are so many great food places to chose from. Lots of great locally sourced seafood. And the area is so beautiful with lots of activities for everyone.

  11. I’ve never heard of this place before. It looks like the perfect place for a weekend getaway! Thanks for bringing it to my attention!

  12. There is certainly plenty of history here – I had no idea it used to be the capital! Those oysters look incredible too, yum!

    1. I had the best Ice cream there. You would love all the amazing flavors but it is so hard to pick .

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