One of the best day trips from Frederick is to Annapolis, Maryland. Annapolis might be best known as the home of the United States Naval Academy, but this waterfront city offers so much more than military prestige.
Bursting with colonial architecture, buzzing restaurants, scenic waterfronts, and a rich maritime culture, Annapolis is a must-visit gem in Maryland.
Whether you’re a history buff, foodie, sailor, or weekend wanderer, Annapolis has something epic for you.
Here’s our ultimate guide to the best things to do in Annapolis, MD!
Rankings: Best Things to Do in Annapolis, Maryland
(Did we miss something? Did we rank something too high or low? Let us know in the comments.)
1. Wander Historic Downtown Annapolis
Why Do It: Annapolis best feature is it quaint, historic downtown. Annapolis is one of the older cities in the US, founded some 300 years ago, and the downtown remains preserved with many original buildings and streets.
Today, downtown is a bustling shopping and entertainment district, all within a compact city center connected with the Annapolis City Dock.
There are several great shops, restaurants, and pubs. Focus your time on Main Street, which connects the City Dock with Church Circle, and is the main drag to wander.
Better yet, book this walking tour and get a guided walk through downtown Annapolis, the Naval Academy, and the State House.
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2. Tour the U.S. Naval Academy
Why Do It: A beautiful campus located right in Annapolis, the U.S. Naval Academy is the institution that prepares young men and women for the United States Navy and Marine Corps.
Besides being one of the finest institutions in America, it’s a fascinating place to tour. While vehicles are prohibited on campus, pedestrians can generally walk freely around campus.
Best ways to tour the grounds:
- Book a Combo Tour (Annapolis, State House, and US Naval Academy) – Highly Recommended!
- Plan a Tour starting at the Armel-Leftwich Visitor Center. Read ID and Ticket Requirements carefully.
Highlights of visiting the U.S. Naval Academy include the U.S. Naval Academy Museum, Bancroft Hall (the largest dormitory in the world), and the formation grounds.
Special Tip: Consider this Annapolis Downtown and Naval Academy Tour for your entire group, which gets rave reviews!
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3. Get a Rooftop Cocktail at The Choptank
Why Do It: There is some great seafood eating in Annapolis with several good restaurants right downtown. However, our favorite by far is The Choptank.
The Choptank is a seafood and crab restaurant serving local catch daily. But its best feature is the incredible rooftop bar that takes advantage of its City Dock location to provide spectacular views of Downtown Annapolis and the harbor area.
The drink menu at The Choptank is also fabulous with cocktails and plenty of local beers on tap (try something from Crooked Crab Brewing).
But the highlight is probably their Crushes– a Maryland coastal drink specialty that combines vodka, crushed ice, and fruity flavors.
Nicole and I visited The Choptank recently in July 2025 for cocktails before setting sail on a sunset cruise.
The Downtown Annapolis Hotels We Recommend:
- Historic Inn Annapolis. Three distinct Inns with Victorian character and modern rooms. Right on State Circle.
- Flag House Inn. A historic Inn with an unbeatable location.
- Annapolis Waterfront Hotel. A luxury hotel that sits right on Annapolis City Dock.
4. Take a Boat Cruise Around the Harbor
Why Do It: Maybe the best way to see Annapolis is from the water.
Taking a cruise into the harbor towards the Chesapeake Bay will give you a full appreciation for Annapolis’ waterfront locale, and let you see the city buildings and surrounding areas from a different perspective.
There are a variety of cruises you can take in Annapolis from a variety of operators. A few recommended options:
- Watermark Journey offers a narrated 40-minute cruise of Annapolis Harbor and the US Naval Academy.
- Schooner Woodwind has a variety of longer cruises from Annapolis, including a 2-hour sunset cruise.
Nicole and I have done the Schooner Woodwind 2-hour cruise the last two summers as part of an organized wine tour with our favorite winery in Maryland: Black Ankle Vineyards. Spectacular!
5. Take an Annapolis Ghost Tours
Why Do It: An American city as old and with as much history as Annapolis is bound to have ghosts. Take a Ghost Tour in Annapolis and hear about the spirits that haunt Annapolis (if that is your kind of thing).
There are several Annapolis Ghost Tours to choose from, but here are the ones we recommend.
- The Original Walking Ghost Tour is a 90-minute, spine-tingling, downtown Annapolis tour.
- Annapolis Ghosts focuses on the pirate and patriot ghost history of Annapolis.
Nicole is a big fan of ghost tours, we’ve done them in lots of American cities. The ghost tours in Annapolis are definitely some of the most interesting (and spookiest).
6. Visit the Maryland State House
Why Do It: The Maryland State House is no ordinary State House. It’s the oldest of all the state capitols, and served as the nation’s capital, hosting the Continental Congress in 1783-1784.
Both beautiful and historic, it’s worth a visit, especially if you are a US history buff.
You can tour the State House on your own, but we highly recommend you book a Guided Tour. This will give you lots more insights into the building’s origins and history.
7. Eat Some Local Seafood
Why Do It: Maryland is known for seafood, and Annapolis is at the heart of this culinary culture. Seafood comes in fresh each day from the Cheseapeake Bay into Annapolis harbor, available immediately for Annapolis restaurants to server up.
A trip to Annapolis is not complete without enjoying some local seafood. Either a quick snack for lunch or an expansive seafood dinner.
We’ve already mentioned The Choptank above, but here are some other of our favorite restaurants in downtown Annapolis:
- McGarvey’s. A pub-style seafood restaurant that specializes in oysters. Right in downtown.
- Chart House Prime. An upscale spot over the water serving seafood and steaks.
- Obriens Prime. Around since 1774 and still the classic Annapolis Tavern.
Special Tip: If you are a real foodie, consider this Annapolis Food Tour, a 3.5-hour adventure that combines history with stops at local taverns, pubs, and restaurants.
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8. Visit the Annapolis Maritime Museum
Why Do It: More than just a museum, this facility has an exhibit hall, art gallery, and hosts a variety of educational programs.
The Annapolis Maritime Museum, located on the waterfront in Eastport, is a cool place to visit to learn about the maritime history of Annapolis. The exhibit hall is small but interesting. Tickets are $7 for adults and $5 for children and seniors.
It’s also a place that you can book a sailing cruise via Skipjack Tours, which schedules regular heritage, educational, and sunset cruises.
Special Tip: You can book an Eco Kayak Tour from this same facility, scheduled regularly on weekends!
9. Annapolis St. Patrick's Day Parade
Why Do It: This is obviously a seasonal event, but Annapolis hosts one of the best St. Patrick’s Day Parades and Festivals in Maryland.
Nicole and I have been many times, and it’s a great experience to be in a town that embraces this Irish holiday with so much enthusiasm.
This is usually a weekend-long event, but the main parade down Main Street happens on Sunday afternoon. Get there early for a good spot along the parade route.
If you are planning a weekend visit to Annapolis, St. Patrick’s Day weekend is a great time to do so.
