Only one more day until Friday! If you’re in DC and looking for a last minute escape this weekend—for a day, a night, or even the whole time—I cannot recommend Annapolis enough. If you’re not nearby, but looking for a cute waterfront town on the Chesapeake Bay where there is a beautiful view at every turn, Annapolis should jump to the top of your list.
Home to the US Naval Academy, the state capitol of Maryland, St. John’s College, and a beautiful waterfront, Monica and I were in love with this town the second we drove up to the Annapolis Waterfront Hotel. Although we both visited Annapolis in the past, neither of us had never spent a night there and we were excited to take advantage of the extra time to explore and enjoy a waterside breakfast at Pusser’s Caribbean Grille.
(Confirmed—breakfast on the water is always better.)
So to help you plan any future trip you may take to Annapolis, I’ve rounded up some of my favorite things to do, see, and eat below!
WHERE TO STAY /
There’s only one downtown Annapolis hotel right on the harbor, so it’s no question where you should stay—Annapolis Waterfront Hotel! Monica and I checked into a room with two queen beds and a beautiful view of the water. Recently renovated, the branding and accommodations at AWF were on-point! We loved the monogrammed pillows, towels, and robes in the room, and appreciated the hotel keys so much we didn’t turn them back in. (#rebels) And as a nod to the nearby Naval Academy, vintage black-and-white shots of sailors hung over the beds—which were so comfy.
But the luxury doesn’t stop in the rooms. We enjoyed a nice bottle of wine overlooking the water and boats in the harbor on the hotel’s second-floor patio, just a flight of stairs away from the popular—and poppin’—Pusser’s waterfront bar. And needless to say, we couldn’t get enough of how the navy and nautical theme carried into the welcoming lobby.
But what really stands out about the hotel is the level of service. The front desk staff were so welcoming, and I really owe the valet staff a cold one. Case in point—I decided after we put our suitcases in the car for the day on Saturday I needed an item out of it. Though this was a super annoying request on my part, they ran and brought me my bag within 60 seconds, and then were so willing to run it back to the car once I retrieved said item. #MVPs
WHERE TO EAT /
When I went to Annapolis last Memorial Day with my friend Emma, we went to Pusser’s Caribbean Grille for a waterfront happy hour. We sat right on their dock and drank shandy for a solid two hours, and I’ve dreamed about going back ever since. So when Monica and I were invited to eat breakfast at Pusser’s this trip, it took me all of two seconds to say YES!
Monica opted for an omelette, and I went for my breakfast go-to: scrambled eggs, turkey sausage, hash browns, and toast. We loved watching people get on their boats for a fun day of sailing, and you just can’t beat the atmosphere set by a Bay breeze. The manager stopped by our table and gave us some awesome pointers about where to shop and shoot pictures.
Though I’m still dreaming about breakfast, Monica and I ate at two other places while we were in town. For Friday night dinner, we opted for Dock Street. A favorite among locals, definitely order a crab cake and don’t share—you’re going to want your own! We sat at the bar and talked to the bartenders, all of whom were from Annapolis. A highlight was when one of them did a green tea shot with us—it sounds terrible, but actually tasted so good. I also cannot say enough good things about the playlist at Dock Street—great country jams all night long.
For Saturday lunch, we popped into Preserve. They source locally as much as they can, and I loved my BLT paired with a glass of local Maryland rosé. The bartender there is super talented, so if you’re looking for unique craft cocktails, homemade soda, or kombucha, it’s worth the trip.
WHERE TO SHOP /
Funny enough, this whole trip even came about in the first place because Monica and I decided we wanted to spend a Saturday in June shopping in Annapolis for our upcoming trip to Charleston for The Blog Societies Conference.
We spent the bulk of Saturday afternoon walking around Main Street, popping in and out of boutiques. If you love the resort wear look, definitely hit up The Lucky Knot and Kokopelli, which also has a great selection of gifts and nautical housewares. If the bright colors and patterns aren’t your thing, definitely check out Lilac Bijoux and Tangerine Boutique, also both on Main.
There are also many art galleries in Annapolis. Some of them are on the pricier side, but, hey, I love window shopping, too!
WHAT TO DO /
Needless to say, a walk around the US Naval Academy should be on the top of your Annapolis to-do list. I would recommend starting at the Visitor Center, where you can take a walking historical tour. Be sure to do your research before you go, as different times of year have different tour schedules, and don’t forget your photo ID!
The Maryland State House, shown on the left side of the photo above, is also worth a visit, even if you don’t go inside. I shot the picture above from an alleyway off Main Street, and then Monica and I walked up to it that way. The view of the Harbor from the steps is unbeatable, and if you’re looking for the history or a formalized tour, the building itself is open daily.
Don’t worry, I saved the best—and most obvious—for last. It’s Annapolis—find a way to get on the water! Schooner Woodwind departs from the Annapolis Waterfront Hotel’s dock, and has a regular schedule of two-hour tours. There’s also the ever-popular Pirate Adventure Cruise option, or if you want something more hands-on, we saw many a kayaking school take the Bay. Whatever you do, make sure getting on the water—even if just for a taxi ride—is on your agenda!
HOW TO GET THERE /
The good news is, once you’re in Annapolis, it is very easy to get around. Everything we wanted to do was in walking distance of the hotel, and if you wanted to venture a little further, Ubers are easy to call. If you’re going from Annapolis to Eastport, the town right next door, it’s easy to hop on a water taxi right at the hotel. The water taxis also stop at popular restaurants, which means you don’t have to worry about parking a car or drinking and driving.
The bad news is, you pretty much either have to boat to Annapolis—it’s situated where the Severn River meets the Chesapeake Bay—or drive there. The closest major airport is BWI, but you could also fly into Dulles or Reagan—the drive would just be longer if you deplaned in Virginia. From the DC area, it’s a quick hour drive without traffic, but in the summer, it can take up to two hours as you’ll be on the same route as Maryland and Delaware beach traffic. But you know what they say—getting there is half the fun!
Thank you so much to Annapolis Waterfront Hotel for inviting us to stay for a night, and welcoming us so warmly with a bottle of wine. Many thanks to Pusser’s Caribbean Grille for a delicious breakfast with an unbeatable view on the water!