How to Spend a Solo Weekend in Annapolis

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One thing I hope to convey about solo travel is that it can be as simple or complex as you want. I personally love shorter trips that are closer to home. If you’re like me, this itinerary for a solo weekend in Annapolis is perfect for you.

Getting to Annapolis

From D.C., it is about an hour drive, which makes this a great weekend trip destination. There is no direct train here, so a car is your best bet. This will also help with some of the places on the list below, as you’ll need a car to get there.

Where to Stay

Eastport: Chesapeake Birdhouse Studio

My personal preference when traveling is to stay in a neighborhood that is close to the action, but not exactly in it. Eastport checks that box. It is a short walk or water taxi ride from downtown Annapolis. As a solo traveler, my stay at the Chesapeake Birdhouse Studio was perfect.

Downtown

I have not stayed in the downtown area yet, but if you want to be as close as possible to the Naval Academy, restaurants and shopping, this is the spot for you.

Day 1: Downtown Annapolis

I usually start any trip by exploring the downtown or most popular neighborhood to get a good feel for my location. After settling into my Airbnb, I walked across the Spa Creek Drawbridge to downtown.

You can also take the water taxi if you don’t want to walk. I used Watermark during my stay, which was fast and only about $10 a trip. They also offer different cruise options if you want to spend more time on the water.

After this, my first stop was to get food and some cute pictures (my two favorite things!). Hands down, the best food I had while here was at Iron Rooster. I’m a sucker for pop-tarts, so had to check out their RoosTarts. Their Waffle Churros are also to die for.

After eating, I headed to Pinkney Street and Fleet Street, which have some great photo opportunities. A photo tour is a free and easy option for solo travelers, as you can set your own pace and not feel strange on your own (Make sure to always be aware of your surroundings though and keep your safety top of mind). I also hit some of the cute boutique shops nearby, including an awesome record store, KA-CHUNK!! Records. Stay tuned for my post on the most Instagram-worthy spots in Annapolis.

Day 2: Kayaking and Old Fox Books

Since I love water activities, I started the next day with a few hours of kayaking in Annapolis Harbor and Spa Creek. Kayaking is another great solo activity, as you can enjoy nature on your own or even with kayaking tour groups. I used Paddle Annapolis for my solo kayaking and had a great time.

After kayaking, I grabbed breakfast at Bakers & Co., and then headed to my favorite part of the trip, Old Fox Books and Coffeehouse.

Old Fox is a local bookstore and coffee shop with an adorable garden patio in the back. I especially loved their Blind Date with a Book option. It was fun to be surprised by what I had picked up, which was Gift from the Sea. Bookstores and coffee shops are always solo travel-friendly. You can find a corner to read or people watch on your own time.

I can’t visit a coastal town in Maryland without mentioning some seafood. For dinner, I loved Boatyard Bar and Grill in Eastport, which had some of the best crab cakes I’ve ever had! I got take-out due to COVID, but takeout is also easier as a solo traveler than sitting in a restaurant on your own, if you’re not quite comfortable enough doing that yet.

Day 3: Quiet Waters Park

As I headed back to the D.C. area on my third day, I stopped at Quiet Waters Park thanks to a recommendation from Instagram. And I am so glad I did!

It is the perfect hidden gem with tons of beautiful scenery and a quiet vibe (hence the name). It was a relaxing way to end my solo weekend in Annapolis.

On my next solo weekend trip in Annapolis, I want to check out:

the U.S. Naval Academy
a water cruise

If you need a unique road trip in the DMV, I hope you will visit Annapolis, whether in a group or solo. And check out my post on other great road trips close to D.C.

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19 Comments

Sabrina DeWalt

at Reply

As much as I love traveling with my husband, one of the challenges is making sure we are both happy with what we do on a trip. While we enjoy a lot of the same things, some of our interests are very different. I would say one of the advantages to solo travel is you can choose to do whatever you want without having to worry about anyone else’s desires.

Jordan

at Reply

Hi Sabrina,
I absolutely agree! It is nice sometimes to not have any other schedules or interests to factor into a trip. I hope you get to travel solo soon!

Melissa Jones

at Reply

It looks like an amazing place to visit! I’ve not gotten there yet, but one day!

Alice

at Reply

I never really thought about Annapolis other than NCIS. Looks like a great place to visit. I usually travel alone when I do travel. It’s a good idea to mention being aware of one’s surroundings when doing a photography tour.

Jordan

at Reply

Hi Alice,
Annapolis is definitely a bit off the beaten track. And nice to meet another solo traveler. It’s always a good idea to remind ourselves of that when we are on our own.