Annapolis, Maryland has always been one of our favorite cities to visit. Nestled on the Chesapeake Bay, it offers gorgeous waterfront views and plenty of fresh seafood. First settled in 1649, it also has a lot of history and charm with its beautiful 18th-century brick houses and roads. Now it’s home to preppy boutiques, inventive restaurants, a vibrant nightlife, and amazing boat (or yacht) watching. Here are a few of my favorite places to visit while I’m there.
For breakfast, I love the Metropolitan Kitchen & Lounge, which is slightly off the beaten path and closer to some of the hotels close to downtown. They dabble in southern comfort foods like Chicken Biscuits & Gravy, but also offer some healthier options like Avocado Toast. My personal favorite is the French Toast with cinnamon butter and cheesy grits. So good! The restaurant is also open for lunch and dinner, staying open until 2 a.m. on weekends. The roof deck is a lot of fun if you’re looking for a fun place to have drinks.
I would also recommend Iron Rooster, which serves breakfast all day, and City Dock Coffee for yummy pastries and quiche. Those are both closer to the water, so you can take your coffee with you as watch the boats sail by.
For a quick lunch, I would recommend Mason’s Famous Lobster Rolls. The name says it all, but the lobster rolls are filled with big chunks of lobster and covered in butter. What could be better? You can also purchase Cape Code chips while you’re there to feel like a real East Coaster. The vibe is fast casual, so you can enjoy your lunch and still have plenty of time explore the city.
The dinner options range in price, but one thing you can rely on is the fact that almost every restaurant offers some sort of fresh seafood option that is bound to impress. It’s tradition at this point to go to Jimmy Cantler’s Riverside Inn for their steamed hard shell crabs. They come out covered in Old Bay Seasoning and are placed unceremoniously on your table, which has been covered in paper. You are given a mallet and a knife, so you can go to work rescuing luscious crab meat from the shell. Dipped in butter, it’s divine.
If you want something that’s a little less work and closer to the harbor, I would recommend Vida Taco Bar. Their shrimp ceviche is some of the best I’ve ever had and their taco options usually promise some kind of fresh seafood. They also have great margaritas. I’ve mentioned it already, but Iron Rooster serves breakfast all day, which means you can order a traditional breakfast meal or a typical lunch or dinner entree with some sort of breakfast flair. I prefer to go with the latter and order the Cakes on Cakes, which features crab cakes on top of fried green tomatoes on top of cornmeal pancakes. One of my all-time favorite meals!
As far as nightlife goes, you can’t visit Annapolis without going to Pusser’s. It’s right on the water and offers the best views. The later you stay, the more bumping it gets, so plan your visit accordingly.
Navel Academy Chapel
One of our favorite places to visit in Annapolis is the Naval Academy. The architecture alone is worth the visit, but it’s also very cool to go on the guided tour and hear all about U.S. Navy history as well as the admission process and education of midshipmen. Fun fact: the crypt of John Paul Jones is located under the Naval Academy Chapel. You may know him by his famous line: “I have not yet begun to fight!” You can also check out the grave of John McCain, who was buried in the cemetery there just last year.
For another fun history lesson, visit the Charles Carroll House and Gardens. The tour itself is free and led by a volunteer docent who will gladly answer any of your questions. The house is not especially flashy and doesn’t include any really cool furniture, but the story is interesting. Charles Carroll was the only Roman Catholic to sign the Declaration of Independence and was the last signer to die.
To get to know both past and present-day Annapolis and enjoy a little time on the water, I would recommend any of their many boat tours. They are all lined up at the dock and can take anywhere from 40 to 90 minutes, focusing on different aspects of the city.
Sometimes just walking through the different streets surrounding the harbor and admiring the old houses is entertainment enough.
One of the things I love most about Annapolis are all of the unique shops that I don’t get the chance to frequent up north. They have several antique stores, most of which are situated on Maryland Avenue. There are countless options, so simply stroll down that street to find the jackpot in nautical antiques. And of course, I can’t pass up a charming book store, so I always try to pop in to Old Fox Books, featuring used and new books and a coffee shop. I inevitably find a cool history book about the area that I can’t turn down while I’m there.
There are several cute fashion and accessory boutiques lining Main Street. Sea Bags features nautical totes that are upcycled from recycled sails.
The Lucky Knot describes itself as the “Ultimate Preppy Store with a Nautical Flair”. Brands include Vineyard Vines, Lilly Pulitzer, and the like.
Visit Lilac Bijoux for casual chic clothing and accessories — something these East Coasters have down pat. I bought the cutest pair of paper bag shorts there.
You’ll notice the distinctive facade of The Pink Crab, a Lilly Pulitzer signature store, as you get closer to the harbor. It’s well stocked with the bright prints you’ve come to know and love.
A new store on my radar is Surf’s Up Candle. They sell 100% natural soy candles inspired by life at the Jersey Shore. They also sell small home decor items.
No matter what you love to do when you travel, there’s something for everyone in Annapolis, so find your favorite spots and enjoy!