Annapolis, Maryland Travel Guide 2019


Annapolis is a quaint city filled with art, history and good food. It’s worth taking a drive outside of Washington D.C. in order to explore all there is to offer. There is plenty of shopping, dining and history to uncover. Located within the town is the United States Naval Academy, an art gallery and my favorite bakery in Maryland.

I’m extremely fond of day trips and this trip might have been my favorite in recent times. I wanted to take you along so there are a couple of videos up on YouTube in addition to a comprehensive guide below! (Part 1 & Part 2)

Things to Do 

United States Naval Academy

The United States Naval Academy is located within its own protective gates but does welcome visitors to the heart of their campus. You can tour the naval academy via a guided walking tour and visit the gift shop within the visitor center.

Address: 121 Blake Rd, Annapolis, MD 21402

Annapolis Maritime Museum

This museum covers the history of Annapolis’ maritime heritage and ecology of the Chesapeake Bay. It is free admission and open Tuesday through Sunday from 11 a.m to 3 p.m.

Address: 723 2nd St, Annapolis, MD 21403

Maryland Federation of Art - Circle Gallery

This art gallery features a lot of great local talent! The main gallery is open Tuesday through Sunday from 11 a.m. to 5 p.m.

Address: 18 State Circle, Annapolis MD 21401.

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Back Creek Books

Here you can find an array of used and antique collector’s books. It’s totally worth a browse if you’re an avid reader.

Address: 194 Main St, Annapolis, MD 21401

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Watermark Boat Tours

You can schedule a guided boat tour with Watermark and learn a little more about Annapolis and the Naval Academy from a different perspective. Tours take about 40 minutes and you can buy tickets at the booth on site. It is $17 for adults on the Annapolis Harbor and U.S. Naval Academy Cruise On Harbor Queen.

Address: : 1 Dock St, Annapolis, MD 21401

Town Center

Otherwise, the town center provides a ton of shopping and dining options that are worth exploring.

Places to Dine

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Bakers & Co

This is one of my favorite bakeries ever. Their lavender lemonade is phenomenally refreshing and sweetened perfectly. Pair this with any of their baked goods such as the pain au chocolate, an almond filled croissant or quiche and you are set for the morning.

Address: 618 Chesapeake Ave, Annapolis, MD 21403


Cantler’s Riverside Inn 

If you have a hankering for crabs, this is a fantastic spot for fresh crab in a cozy ambiance. Crab is prepared here in a variety of ways ranging from soft shell to by the l/b in various sizes. It is served over brown parchment paper and prepare to get a little messy as you crack into your delicious Old Bay seasoned crabs.

Address: 458 Forest Beach Rd, Annapolis, MD 21409


Sofi’s Crepes 

This is a great spot for savory or sweet crepes to go. On this visit, we went for a savory option but I will definitely return for some dessert next trip!

Address: 1 Craig St, Annapolis, MD 21401

I hope you found this guide helpful and informative! If you have any questions, comment below! Thank you so much for reading everyone!


Christine Chhatwal