Even though I live only a few short hours away in Richmond, I had never been to Annapolis, Maryland until recently. Seriously y’all, I had been missing out. My husband, daughter, and I spent three days exploring, learning history, and eating our way through Annapolis, and I fell in love. I kid you not when I say that during our drive home we were already trying to plan our next visit!
It is not only picturesque and quaint, but the city is full of history and so much to do! So, whether you’re looking to schedule a family trip or maybe just a weekend away with friends or your significant other, you have to visit! Read on for my Annapolis weekend guide full of restaurant recommendations, must-see historical sites, and hotel recommendation!
We stayed at the Hilton Garden Inn Annapolis Downtown, and y’all, the location was perfect. Walking out the doors, there were restaurants within a block to both the left and right of us. And the cutest little shops were only a few blocks further downtown.
Being that Annapolis is right on the water, I was obsessed with all of the nautical details of the hotel. Each room had this amazing wallpaper, featuring blue prints from the Naval Academy and artwork from local Annapolis artists! The lobby and restaurant area were equally as stunning. I loved the paper sailboat installation and the ceiling-high bookshelves. The hotel was super-chic with a local-infused, boutique feel, which I love!
They also have a restaurant and a full bar, which is so convenient! Aaron sampled one of their craft cocktails and loved it! We also had a chance to eat breakfast there before checking out to head home. I definitely recommend the french toast (the fruit compote is AMAZE.), and Aaron loved his breakfast skillet!
The food, y’all. Oh the food. Being pregnant meant I didn’t get to indulge in any cocktails or wine. But you know that I ate allll the food. 😂
Breakfast + More
If you are a breakfast food lover then listen up. There are two stops you have to make! Both Iron Rooster and Miss Shirley’s serve breakfast all day (along with pretty extensive lunch and dinner menus too!). Even if you don’t eat breakfast, you have to try the gourmet pop tarts at Iron Rooster. They were the very first thing I had in Annapolis, and they left such an impression that I thought about them the rest of the trip! (We tried both the berry and the brown sugar. The brown sugar were my fav!)
At Miss Shirley’s I had to try the top-rated Southern Slammer Sandwich with fried green tomato, avocado, and egg. (Are you salivating yet?) It was named the Best Breakfast Sandwich in America by Restaurant Hospitality Magazine, and I’d have to agree. It was SO GOOD and also huge. We also split the Monkey Bread, which is a must for the sweet tooths (teeth? 🤔) out there! Miss Shirley’s has also been featured on Diners, Drive-Ins, and Dives if you’re a Food Network fan!
If you want seafood, head over to Eastport, just a few minutes from downtown and go to Boatyard Bar and Grill. I had the crab cakes, and I kid you not when I say they were probably the best crab cakes I’ve ever had. They had almost zero filler, which meant tons of delicious crab meat. Baltimore Magazine also called them the “best crab cakes,” so I feel like I could probably qualify as a legit food critic now. 😉 I also sampled the scallops and was equally as impressed with them. The restaurant definitely has a laid-back, local vibe, so no need to dress up! But if you come on the weekends, be prepared to battle the crowds!
You didn’t think I was going to let you off without a dessert option, did ya?! For a seriously amazing scoop (or two, or three–no judgement here!) of ice cream, you have to hit up The Red Bean. It is both an ice cream shop and coffee house, and if you think those don’t go together then think again! Try their affogato (ice cream with a shot of espresso!), and your life will be changed. Not a coffee person? They mix over 50 different topping options together for you to make your own custom ice cream. I personally tried vanilla mixed with banana and peanut butter and was as happy as a clam!
Ok, I’m sure most people aren’t going to Annapolis just for the food, so let’s chat history! Annapolis is so rich with history. It actually served as the very first peacetime capitol of America! It is also the place where George Washington resigned his post as Commander in Chief of the Continental Army!
Maryland State House
You can stand in the same room where Washington resigned and see the actual resignation letter Washington penned by hand at the Maryland State House! The history nerd in me definitely came out when I saw that letter in person! But if you’re more into pop culture than history, you should still pop into the State House to see the House of Delegates chamber, where House of Cards filmed! To get all the best info, I’d recommend booking a tour with Watermark Tours. Hearing from the experts is always more interesting and informative (for history and pop culture facts!) than trying to muddle through solo!
US Naval Academy
Annapolis is also home to the US Naval Academy, which you can also tour! Again, we participated in a guided walking tour, which was so much more fun and informative than stumbling through it on our own. Bancroft Hall, the only dormitory at the USNA, was seriously breathtaking. I also loved seeing the Chapel, which houses several Tiffany stained glass windows!
You can’t go to Annapolis without taking in the water activities! Be sure to book yourself a tour on the Schooner Woodwind. I actually had to opt out of the sail because of the weather. (Choppy waters, motion sickness, and pregnancy don’t exactly go together well! 😂) But I’m so jealous of the ladies who went! Even with the rain and wind, they couldn’t stop talking about what a wonderful experience it was! During the week, the cruises are themed with local music or beer tastings! On the weekends, you can enjoy a sunset cruise while sipping a cocktail! Fun fact: the Woodwind was used in the filming of Wedding Crashers!
If you prefer to stay on land, you might want to take a trip to the Annapolis Maritime Museum in Eastport. It’s situated right on the waterfront with the most gorgeous views. The museum is actually located inside the last surviving oyster packing plant in Annapolis and contains tons of information about oyster harvesting and how it impacted Annapolis over the years. There is also access to a public beach right around the corner at Horn Point Street End Park! (And the previously mentioned Boatyard Bar and Grill is also within walking distance!)
You can’t go to Annapolis and not explore its quaint streets and shopping district! Hit up Main Street to check out the cutest locally-owned shops and boutiques! The area also houses restaurants (like Iron Rooster and The Red Bean! 😉) and bars, and has picturesque views of the harbor! I could’ve probably spent an entire afternoon snacking and shopping Main Street! 😂
So, tell me: when you travel, what is most important to you? The food? History? Shopping?
*This post was created in partnership with Visit Annapolis, but my love and enthusiasm for this amazing city are all my own!!*