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Downtown Annapolis is charming, historic, and known as the sailing capital of the United States. The sailboats, colorful row houses, and local shops make it the cutest downtown I’ve ever seen. It’s one of the least populated state capitals in the country, making it very walkable with a small town feel. There’s a lot to do and see in downtown Annapolis, but I’ll start with sharing 6 Instagram worthy photo spots. Keep in mind that downtown is quite small, so it will be easy to hit all of these spots in one afternoon!

1. Pinkney Street

Pinkney Street is an adorable historic street, lined with colorful row houses. Downtown Annapolis is full of row houses, but these super bright colors make it the perfect photo spot. The Shiplap House is also located on the street, and it’s one of the oldest surviving buildings in Annapolis, built around 1715.

2. Ego Alley

Ego Alley, also known as City Dock, is another great photo spot! It’s actually not an alley, but a waterfront area with beautiful ocean views. There’s lots of sailboats, people walking around, and events throughout the year. They have firework shows on the 4th of July and New Year’s Eve, summer concerts, and boat and sailing tours. The Annapolis Spring Sailboat Show is also a super popular spring event.

I love hanging out here in the summer, grabbing an ice cream cone from Storm Bros. Ice Cream Factory, and walking my dog around the dock. It’s the perfect spot to spend an afternoon and to snap some photos.

3. Maryland Avenue

Maryland Avenue is my favorite street in downtown Annapolis because of the brick streets, local shops, and view of the Maryland State House. The Maryland State house is not only beautiful, but it’s also the oldest state capital in the U.S. with continuous legislative use. You’ll want to take a photo from outside of Natalie Silitch, which is an antique shop on the street with an impressive view of the state capital. 

Some of my favorite shops on Maryland Avenue are KA-CHUNK!! Records, Mango and Main, Brown Mustache Coffee, and Blue Crab Antiques, Inc.

4. Old Fox Books & Coffeehouse

While you’re on Maryland Avenue, you have to stop into the Old Fox Books & Coffeehouse! If you love books, antique decor, and coffee, then this is the place for you. The coffee shop inside the bookstore is called Brown Mustache Coffee, and there’s a seated patio in the back with a garden. Both the patio and the bookstore are great for photos, and I’ve spent many afternoons on my laptop here with an iced coffee.

5. Wisteria Mural on Fleet Street 

The Wisteria Mural was painted by Mary Bowen on the wall of Chez Amis Bed and Breakfast. The mural is a cute photo spot, and the entire street is filled with row houses that are very photo worthy. There’s also a bright blue building that looks like a barn directly across from the mural, with a nice view of the Maryland State House. Fleet Street is located next to Pinkney Street, mentioned above.

6. Main Street Alleyway

Main Street is probably the liveliest street in downtown, filled with local restaurants, boutiques, coffee shops, and dessert spots. It’s also super dog friendly! It’s the perfect date night spot, and there’s a photo op that you can’t miss in the alleyway located between Alpaca Internacional and Vida Taco Bar.

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