Situated on several large tributaries of the Chesapeake Bay, Annapolis is the capital of Maryland. There is water, water everywhere, and, fortunately, also lots to drink. But I’ll get to that in a bit. Annapolis is a quaint, historic city with lots of heart and personality, perfect for a long weekend with the family, a girls trip for some good food and spa time, or just a nice daytrip from Baltimore or Washington, DC. I’ve called the Annapolis area home for the last 6ish years, but I’d been visiting and threatening to move here since I was a kid. Thus, I have appointed myself as an expert on Annapolis and, fortunately for you, I’m going to share my expertise with you.
So without further ado, if I only had 36 hours to experience Annapolis, here’s what I would do:
Day 1
On your first night, you should check out the food and bar scene around downtown. Head to The Pearl for a cocktail at their cool downstairs bar or at their upstairs Ponche Tiki Bar. The Pearl’s location in the heart of Annapolis’s historic City Dock is the perfect place to kick off your visit.
My dinner favorites downtown would either be Vida Taco Bar or Dry 85. The nachos and buffalo cauliflower tacos at Vida are highlights, and the Purple Drank (a mix of sangria and margarita) is dangerously delicious. Dry 85, which has a kind of industrial speakeasy vibe, offers a seasonally-rotating selection of craft cocktails and a ton different bourbons, which you can conveniently try as a flight. I personally like the Skirt Steak and Quinoa Salad because fried goat cheese balls. The truffle fries are also a great accompaniment to pretty much any dish.
Round out the night on West Street at Rams Head On Stage with some live music (you can check their website for upcoming performances). Sip on one of the in-house Fordham brews, which feature a rotating selection of classics as well as seasonal flavors. If you’d like somewhere a bit more off the beaten path, wander over to Maryland Street near the State House and sip on a hard cider at Galway Bay Irish Restaurant. Featured on Diners, Drive Ins, and Dives, the dark wood and traditional pub music will transport you right to Temple Bar. And if you’re in Annapolis around the holidays, try their eggnog. It’s legendary.
Day 2
Start the day off strong with breakfast at Rise Up Coffee Roasters. There are two Rise Up locations in Annapolis, but only the Somerville Road location has food. I usually go for a scrapple breakfast sandwich on a biscuit, but I’ve heard many people rave about their breakfast burritos. For those of you that read my post on the Waterfowl Festival in Easton, you already know my love for Rise Up.
After you’re appropriately caffeinated, there are a number of different options for activities. If you’re traveling with kids and it’s sometime between late April and early October, check out Annapolis Pirate Adventures for a swashbuckling good time. If you’re traveling sans kiddos, I’d recommend a day of browsing, sipping, and nibbling. There’s really something for everyone. Stop by the Spice and Tea Exchange (literally nowhere smells better), or pick up some gifts at The Cottage on Main. For the Irish among us, pop into Irish Traditions for a look at their collection of tartans and Irish wool garments. Sea Bags, which started up in Maine, uses recycled sails to make their bags. There are also numerous ice cream shops (my favorite is Annapolis Ice Cream Company), a Christmas shop, an olive oil shop, and much more.
One of my favorite parts of Annapolis as of late are the plethora of murals that have popped up downtown. The Equal Justice mural, located on South Street across from the courthouse, features portraits of Thurgood Marshall and Ruth Bader Ginsburg. There’s also a mural nearby at Stan and Joe’s Saloon on West Street celebrating local musician, Eva Cassidy. A new mural, named “The Best Place- For All”, was recently completed at 44 Calvert Street, which celebrates iconic Anne Arundel County citizens, landmarks, and culture. There are plenty more as well, but those are some highlights to look out for.
The best hidden gem in Annapolis is the Eastport neighborhood. Located just over the Spa Creek drawbridge from downtown, the “Maritime Republic of Eastport” is a beautiful peninsula neighborhood. Stop by Forward Brewing for a happy hour brew. Take a walk over to the Annapolis Maritime Museum to see if they have any events going on, or just to take in the lovely water views. Enjoy dinner in Eastport at Davis’s Pub, which has some of the best local crab cakes in my humble, native-Marylander opinion, or treat yourself to Vin 909 Winecafe for an elevated farm-to table meal.
Day 3
Start your last morning in Annapolis with brunch at Miss Shirley’s. I highly recommend starting with their monkey bread. Their chicken and waffles are also delicious. Depending on the weather, you can spend the rest of the morning exploring the grounds of the Naval Academy, visiting the Banneker-Douglass-Tubman Museum, or heading down the highway about 15 minutes and taking in the views of the Chesapeake Bay Bridge from Sandy Point State Park.
Obviously, my recommendations are a non-exhaustive list. There’s something for everyone in Annapolis, whether they’re a history buff, a boating enthusiast, or just looking for a fun little city for a getaway. Below is a list of other recommendations to help you choose your own Annapolitan adventure. Enjoy your trip, and let me know your favorite spots!
- Restaurants and Coffee Shops
- Salons and Day Spas
- Arts and Culture
A Slice of Kate 
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