Most of you may not know that I grew up in Annapolis, Maryland.  I loved the area so much.  I spent six summers of my life singing and dancing at the local summer theater, and I’m proud to call the local high school my alma mater.  So, you can imagine I jumped at the chance to take my family to my hometown for a visit. 

I’d like to thank Visit Annapolis & Anne Arundel County and Westin Annapolis for hosting my family for this wonderful trip down memory lane. 

Any trip to the Annapolis area should start with downtown.  A stroll down Main Street ends at the gorgeous harbor overlooking the Naval Academy. 

My kids had to stop to “quack” at the ducks swimming in the bay and check out the Kunta Kinte – Alex Haley Memorial at the foot of Ego Alley.

I love that this statue reminds visitors to stay connected to their roots.  It is fitting considering our trip back to my hometown. 

Just across from the memorial, we stopped by Market House for a little street-side live music and yummy carryout.  This is a great family-friendly food stop with tons of outdoor seating. 

After lunch, we toddled off to find a treat.  That meant we were headed to Storm Bros.  I have so many wonderful memories of this Annapolis staple.  The owner has six children and nine grandchildren, and he treats every little visitor like one of the family.  Add to that, he serves absolutely delicious ice cream, and this is a “must stop” on my list. 

You can’t say you’ve seen downtown Annapolis without getting out on the water.  There are two good options.  You can take a memorable cruise around the waterways with Watermark Cruises or a quicker adventure on a local water taxi.  Watermark Cruises offers a 40-minute ride around the Annapolis Harbor and Naval Academy.  There is a full bar on board and your own snack are welcome too (no drinks). 

If you don’t have that much time, hop on a local water taxi.  You can quickly cruise across to the Eastport area or your favorite local restaurant.  I highly recommend a piece of their famous mile-high Mud Pie.  It is ice cream Oreo-crusted goodness.  The lounge area has comfy couches that overlook the bay.  It is the perfect spot for a family to enjoy the view and a wonderful memory.

We were lucky enough to be able to visit during the annual Maryland Day Celebration.  Many of the local attractions are free or $1 for the event.  With sick kiddos in tow, we weren’t able to enjoy as much of the historic beauty as I would have liked, but there are so many options for your family to enjoy.  Check out the Maryland Day website for all the family fun. 

We had so much fun at the Visitors Center though.  They set out the most adorable colonial outfits for the Maryland Day fun, and my kiddos loved trying on the fun costumes.  Seriously, does it get any cuter than this?

Now, if you are looking for a family-friendly restaurant with amazing food, then you should definitely check out Iron Rooster.  We enjoyed breakfast for dinner because why not?  I mean, they serve spicy, candied bacon, come on!  We sat in the upstairs back room, and the staff was even nice enough to put Paw Patrol on for the kids.  Win Win.

It was such a special treat when I got to experience something new while we were in town.  The Pride of Baltimore II tall ship was in port, and they were offering free deck tours for Maryland Day.  My kids kept saying that they wanted to take a ride on the “pirate ship”, so of course, I had to make that happen.  It was a huge hit.  This gorgeous ship will be featured on season 7 of Bravo’s hit TV show, Below Deck. 

Obviously, I’m pretty partial to this beautiful town full of so many of my childhood memories.  That endorsement aside, this is a “must visit” town for any family.