My father and I had the perfect getaway weekend in Annapolis Maryland! It’s been a long time since we spent time together but now that my father is retired, we decided to take the quick 45 minute drive from DC to explore this charming waterfront city. From waterfront dining and quaint cobblestone streets to hidden spots only the locals know about, Annapolis proved to be the perfect place for a weekend of relaxation and adventure. Here are some of the best places we visited and fell in love with along the way.
Main Street Apartments
Main Street Apartments are the perfect place in downtown Annapolis to stay. This historic building is rennovated with modern applicances and literally steps away from all the shops and restaurants. I had the absolute pleasure of creating content for this Airbnb. It’s stylish and spacious with 2 beds/1 bath with a bonus sunroom! Although it was cloudy most of my trip, this apartment still had lots of natural light which is a must for me. The best part of these apartments are the proximity to everything. You just walk down the stairs and you’re at the heart of historic Annapolis. You can even view the Maryland State House from the main bedroom. Book this cozy apartment here.
GameOn Bar + Arcade
A short 5 minute drive from downtown, lies this awesome retro arcade. GameOn offers coin-operated retro games, food and drinks at an afforadable price. I spent less than $10 (probably about $6 but I cant remember) on tokens between my father and I to play games from PAC-Man to skeeball. Really cheap considering how much you would pay to play at modern arcades such as Dave & Buster’s. They do have a bar and kitchen with delicious drinks and your usual “game entertainment” food. My father and I ate beforehand so we didn’t get to try the menu. Make sure you bring cash as you’ll need it to get the tokens to play the games. There is an ATM machine but just bring cash to avoid paying those fees.
William Paca House & Garden
Step back into time to the 1700s by doing a tour of this restored estate of the former Maryland governor and one of the signers of the Declaration of Independece. This tour showcases the extravagant life of William Paca and his wife. Quite fascinating to see how the house would have been showed back in the day including period furnishes and paintings. You’ll also learn about the servants and enslaved individuals who lived in the home. Prior to this tour, I had no clue who Paca was but it gave me some new insight to the city of Annapolis and his influence at the time. There is also a gorgeous 2-acre garden to stroll. We went during the holidays so unfortunately we weren’t able to see it in its glory.
Oscar’s Coffee
Hands down Oscar’s is my FAVORITE place in Annapolis. This coffee stand is right over the bridge in the Eastport neighborhood with views of the marina. This stand is neighborhood and dog friendly. You’ll see people walk up with their dogs and its just the cutest vibe (I’m a huge dog lover hehe). Oscar’s offers dog treats and a dog bowl of water so there’s no shortage of doggies in line with you. The last time I went, I was immediately greeted by a customer’s dog. My go-to coffee order is a matcha latte with oatmilk and vanilla. The matcha here is good and I appreciate it not being extremely hot. I’m a bit tempertature sensitive so I was able to enjoy my latte right away. Also the views here of the marina are just special.
Naval Academy
How can you visit Annapolis without stopping at the Naval Academy?! You can not go anywhere in Annapolis and not see someone walking around in their uniform or jogging in their naval sweats. My father brought the driving tour and it surpassed my expecatations. Our tour guide drove through the campus giving us not only historic facts but antedotes from former students. There’s also a cementary of notable Naval officers including former U.S. senator John McCain. After learning all the sacrifices these individuals make when making the commitment to the Navy, I have a new found respect for them.
Boatyard Bar & Grill
No trip to Annapolis is complete without indulging in the infamous Maryland blue crab! Boatyard was my favorite spot to eat NO FILLER crab cakes. The crab cakes are so succulent and filling with classic side dish options to complete the meal. If crab cakes aren’t your thing, then there are plenty of fresh seafood options such as oysters, halibut, and more. This restaurant is an Annapolis gem located in the friendly Eastport neighborhood.
Rise Up Coffee
Located inside the historic Annapolis Market House at Market Space and Randall Street, the coffee here is the best in the area. My matcha oatmilk latte was hands down the best I’ve ever had, Like the name, it definitely woke me up and had me ready to pound the streets of Annapolis. Service is quick and friendly and you can buy whole beans as well!
Bread and Butter Kitchen
Another Eastport favorite!! Don’t be offput by the basic building — this diner whips up some delicous breakfast and lunch items that are locally sourced and made from scratch. You can see the staff cook your meal which makes this place even more inviting. This is also facing the marina (like Oscar’s) so when the weather is right, you can enjoy your food with a view of the docked boats. This is definitely a hidden gem for that homemade meal with neighborhood vibes that you’re looking for.
Have a favorite place to visit in Annapolis? Let me know in the comments 😉
