Hi there! For stop #5 of my 50 state challenge, I visited Annapolis, Maryland! I’ve visited Annapolis many times, and it is always so much fun. Annapolis is a great place for a weekend getaway, or as a day trip from DC! Annapolis is a small city with lots of history and it’s filled with beautiful, colorful buildings. Keep reading for my guide and recommendations for how to spend the perfect afternoon in Annapolis, Maryland!

Fun things to do!

Annapolis is quite small – so it’s definitely possible to do everything on this list in a single afternoon!

Explore the Historic District

The Historic District is definitely my favorite part of Annapolis! In the Historic District you’ll find landmarks like the State House, as well as the William Paca House. I love walking around the Historic District and taking photos. The homes are so cute and colorful, and the little streets are really charming!

Visit the State House

The Maryland State House is located in the Historic District of Annapolis, and is a great place to visit! You can tour the State House, or just enjoy the beautiful lawns and green space. When I visited, there were many people reading books and hanging out enjoying the beautiful weather.

Visit the Naval Academy

I visited Annapolis for the first time when we dropped my cousin off at the Naval Academy! Since then, I’ve visited Annapolis a handful of times (including for a Naval Academy graduation!) and I always like to walk through the beautiful campus.

Eat Lunch by the Water

There are tons of great restaurants in Annapolis! If you like seafood, you should definitely try some of the wonderful restaurants on the waterfront for lunch or dinner. If you’re looking for a quick lunch, I really like Sofi’s Crepes. I got mine to go and ate it on the waterfront, and it was really enjoyable! Sofi’s Crepes also has good vegetarian options!

Check out Kilwins + The Annapolis Ice Cream Company

Both Kilwins and The Annapolis Ice Cream Company have delicious ice cream! I highly recommend trying them both – they make perfect afternoon snacks! Kilwins also has other yummy treats, like fudge, caramel apples and specialty chocolates.

Visit the Galleries + Shops

Annapolis is home to many lovely art galleries and adorable shops. You can spend an entire afternoon visiting the galleries and checking out the stores. If you’re into preppy clothing, you’re also in luck, because Annapolis is filled with many cute boutiques!


Spend the Night or Weekend!

As I mentioned, Annapolis is a great weekend destination! Although it’s a small city, and you can visit many sites in a single afternoon, it’s a lovely place to spend a relaxing weekend.

When I visited Annapolis in high school, we stayed at the The Maryland Inn . I remember loving the hotel, especially because it’s said to be haunted! The location of the inn is also fantastic, right in the historic district near tons of shops, bars and restaurants; and just a few blocks from the waterfront. Click here for nightly rates and to book! To check out more hotels in the area, click here.


Thanks so much for reading my recommendations for how to spend the perfect afternoon in Annapolis, Maryland! This little city really has so much to offer, and it makes for a lovely and unique getaway. As always, we truly appreciate you sharing this post with others.

Click here to check out my 50 state challenge post, and here to follow along on Instagram!

♡Kate

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10 Comments

  1. We just got a Kilwins out here! I’ll have to give their ice cream a try! What a great way to spend the day in Maryland. I love how the buildings have a historical architecture to them.

  2. Annapolis, Maryland looks so cute! I love the mix of colourful buildings with sweet treats! (crepes aaaand icecream!? – sounds like a tasty afternoon!)

  3. I have not visited Annapolis although I have been to DC a couple of times. Ice cream from The Kilwins and the Annapolis Ice cream company sounds delicious! I would love to walk though the historic street. I guess it’s time to make that day trip to Annapolis the next time I am in DC! 🙂

  4. I visited Annapolis, Maryland during my 8th grade field trip and remember loving it! I will need to make my way back to that area now that I’m older and experience it from a more mature perspective. It looks like a lot of great foodie spots there too. I love Kilwins! 🙂

  5. I was going to Annapolis to visit a family member but we didn’t do all these fun things that you have here. I do love the seafood and the oysters on the half shell.

  6. Annapolis looks like a great weekend trip. I would love to eat by the water and try the ice cream . Thanks for the great guide.

  7. I’ve never been to Annapolis, but it looks like such a cute town! I think I would love to stroll and shop through the cute boutiques 🙂

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