10 Things To Do In Annapolis

Since Caitlin and I both live in Annapolis (and love it!) we wanted to make a list of things to do in our adorable hometown. Annapolis is definitely a must-visit since it is the capital of Maryland, but the charming waterfront Downtown area is another reason to visit this summer. Here are 10 things that Caitlin and I love in Annapolis and suggest you do when you make the trip — and in the next few weeks we’ll be sharing a more comprehensive guide to Annapolis including our top places to eat, shop, stay and more! 

1. Pizza & Wine at Vin909.  There is a reason why this is #1 on our list!  This place is a gem. Located in Eastport in a small, quaint house-turned-restaurant, Vin is a restaurant frequented by locals. Their pizza is to die for, but they also have incredible apps and salads. They don’t take reservations, so expect a wait, but we promise that it’s worth it — you can enjoy a glass (or bottle!) of wine on their front lawn while you wait. 

2.  Take a stroll down Maryland Avenue. This street is one of Annapolis’ cutest streets and has an incredible view of the Statehouse and is often over looked. While you are on Maryland Ave, we suggest you pop into Navette– a chic consignment shop run by two local sisters and then grab a bite across the street at Galway Bay. It’s a great Irish pub and was featured on Food Network’s Diners, Drive-Ins, and Dives! 

3. Must-Shop Boutiques. Lilac Bijoux on Main Street is a must-visit, as well as Wrabyn on Annapolis Street. Both shops are unique to Annapolis and offer fashionable, on-trend clothing for ladies that love style. 

4. Crabs at The Point. A visit to Annapolis wouldn’t be complete without crabs! The Point isn’t downtown but it is worth the little drive for the water view and chill atmosphere. 

5. Visit the Naval Academy Grounds. We are so fortunate to live in the hometown of the United States Naval Academy. The grounds are beautiful and there is so much history to learn.

6. Take a walk or jog around Quiet Waters Park. Since this list is slightly dominated by food, we figured we should include something that involves physical activity! In all seriousness though, Quiet Waters is a beautiful park and the perfect place to take your dog, go for a walk or bike ride. You can also rent kayaks, paddle boards and boats. 

7. Visit Hobo’s Flagship Store Founded in Annapolis in 1991, the popular leather handbag and small leather goods company has it’s one & only brick and mortar store in the heart of Annapolis! Of course Hobo products are available online and at other retailers, but the Flagship store really captures what the brand is all about.

8. Coffee Break at Bakers & Co This adorable coffee shop in Eastport not only has the best coffee, but their fresh bread, pastries, and treats are delicious. Be sure to get there early as they frequently sell out of their most popular treats and bread. 

9. Water Taxi to Eastport Take the water taxi from the City Dock the short ride over to Eastport and walk around this quaint part of town. Stop into Davis’ Pub for one of their famous crab pretzels! 

10. Happy Hour at Severn Inn Enjoy beautiful water views and watch the boats at Severn Inn, they have an awesome selection of appetizers on special during happy hour and is one of our favorite spots. 

Image by Krista Jones of Caitlin shopping on Maryland Avenue