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6 Best Things to Do in Annapolis this Weekend

Updated: Apr 1, 2023

Maybe you are looking for a travel spot for Memorial Day weekend? Or maybe you just want to get outside of the big city and on the water? Annapolis is just a short drive from Baltimore airport or even DC and is the perfect spot for a weekend getaway. If you are looking for things to do, here are my best spots to visit in Annapolis for a weekend.

1. Indulge at Annapolis Ice Cream


The Ice Cream Company has 36 rotating flavors made of super-premium ingredients. The line can be a little long on a hot day, but it’s the good stuff and worth the wait. I love pretty much anything with peanut butter or chocolate, but it’s impossible to go wrong no matter what you try.



2. Get out on Chesapeake Bay!


Two of the most popular ways to get out on the water are on with Watermark Cruises or the Schooner Liberté. The Annapolis Harbor cruise with Watermark gives you a glimpse into the city’s history as you cruise around, past the Naval Academy, and within view of the Chesapeake Bay Bridge. We hopped aboard a sunset cruise with a bar to sip on a beer and watch the sun go down over the bay!



3. Visit the Naval Academy


One of the most popular things to see in Annapolis is the US Naval Academy. On a 90-minute tour, guides take you through some of the main campus highlights. You may even get to see some students in training!



4. Eat all the Seafood


No stop to the water is complete without consumption of its local cuisine. Head to Carol’s Creek Café or O’Leary’s Seafood for a spot on the harbor. Be sure to get there early or make a reservation as the summer can be pretty crowded.


5. Wander the Shops on Main Street


Maybe you stop at Rams Tavern for some live music or explore the hidden art galleries along the way. There is something for all with more than 90 stores, including wine, pottery, home furnishings and spices. Grab an ice cream and start to wander!



6. Visit William Paca House


This grand colonial-era home was completed in 1765 for William Paca, a signer of the Declaration of Independence and Governor of Maryland. The home spent several years as the lobby of a hotel, but now offers one of the best gardens in Annapolis. You can visit the restored home which offers historical artifacts and insight into the life of William Paca.




Bonus: Enjoy a homemade RoosTart pop tart for Saturday brunch with your mimosa at the Iron Rooster.



Mid-range hotel accommodations: The Graduate Hotel Annapolis offers affordable mid-range pricing in Annapolis’ Art District. The hotel has secured on-site parking, a fitness center, and specially designed themed accommodations. This location, as expected, features a nautical theme!




With so many options, it's easy to explore the best things to do in Annapolis for a weekend!

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