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6 Things to Do in Annapolis to Experience the City the Right Way



Whenever vacation season comes, it can be very difficult to decide where you want to spend your money and your time off work. In the end, you just have to know what you like. So if you’re into waves, the sea, and everything to do with the deep blue, Annapolis, Maryland is the right destination for you! But don’t book your flights just yet—check out these amazing things to do in Annapolis, which you can find or do without spending an arm and a leg!

1. Sail the waters of Chesapeake Bay

Chesapeake Bay
Source: Flickr.com

Annapolis is, first and foremost, the United States’ Sailing Capital. This is mainly because the city of Annapolis holds the estuary, Chesapeake Bay, a haven of aquatic life and the state’s main source of seafood.

While there are many ways to cross the Chesapeake Bay, such as riding a bike across the bridge, the best means of doing so as an Annapolis first-timer is to sail across or around it. 

Not every state or vacation destination in America has its own personal waters to tread on the regular, so sailing on the Chesapeake as the sea breeze caresses your face would be such a worthy way to go.


  • There are many available boat services that offer group rides or rent boats.
  • Make sure you know how to swim or possibly maneuver a boat in case of emergencies.
  • Try to ride the waves with a group of people because it’s much safer and it’s much cheaper when there are more of you

2. See the city’s iconic naval monuments

Annapolis Maritime Musuem
Source: Pinterest.com

As America’s center of sailing and one of the main hubs of seafood, largely due to its connection to the Chesapeake Bay, Annapolis’ history has long been intertwined with ventures in the estuary, or really just in the water in general.

See some of the surviving relics of Annapolis history and relive the glory days in these venues:

  • Annapolis Maritime Museum & Park

Entrance fee: $8 per person (1-hour private tour), $2 per person (1-hour family your), $75 for 12 persons & $6 per additional person (1-hour educational tour), $1 for headphones rental (25-minute, audio-guided self-tour)

Note: Call the Museum office ahead of time for a tour because there is are published specific opening hours online.

  • US Naval Academy Museum

Entrance fee: $10.50 per adult, $9.50 for seniors $8.50 for children (all for guided tours)

Opening hours: 9 am to 5 pm (Monday-Saturday), 11 am to 5 pm (Sunday)

3. Tour Annapolis’ Historic Monuments and Buildings

William Paca House and Garden
Source: Flickr.com

Similar to many other state capital cities, Annapolis has its own unique history of events that lead to its freedom, which also means Annapolis is home to many a historical monument and spot.

For starters, you can visit these locations that hold a special place in the heart of the city of Annapolis:

  • William Paca House and Garden

Entrance fee: $10 per person 

Opening hours: 10 am to 5 pm (Monday-Saturday), 12nn to 5 pm (Sunday)

  • Hogshead

Entrance fee: subject to appointment

Opening hours: 12 pm to 4 pm (Saturday-Sunday)

Note: This building will reopen in March 2020.

  • Fort Meade NSA Cryptologic Museum

Entrance fee: subject to appointment 

Opening hours: 9 am to 4 pm (Monday-Friday), 10 am to 2 pm (every first and third Saturday monthly)

4.Wander around the Colonial Annapolis Historic District

Annapolis Historic District
Source: Planetware.com

When in Annapolis, it is crucial to tour around the European-style colonial historic streets of the city. 

Remnants of the city it first was, the colonial structures of the district have been very well-preserved, with some of the original structures and revamped colors to look more alive as it was when it was first seen. 

Not only is this historic district behind why Annapolis is the first city in America to be named a National Historic Landmark, but it is also a major reason for America’s surge in tourism. 

You bet this whole colonial district has been photographed more than ever due to the rise of Instagram culture!

5. Visit the Maryland State House

Maryland State House
Source: Flickr.com

As a venue of state politics and governance, the Maryland State House is situated right in the heart of Annapolis

This gorgeous house is not only a relic of the state’s history but also a driving force for Maryland authority, as it has been used as a state capitol since 1783, making the Maryland State House the oldest and longest-serving American state capitol.

The items within the house are antiques that are accurate representations of the 18th-century decor. The house itself has been restored with modern materials so it can withstand the test of time.

Remember to check out the General George Washington commission resignation exhibit before heading out!

Entrance fee: none

Opening hours: 9 am to 5 pm (Monday-Sunday)

Note: Bring some photo identification for easier access to the statehouse.

6. Get a taste of Annapolis Cuisine

Annapolis Cuisine
Source: visitannapolis.org

In Annapolis, you always come back to the sea. 

Because of its fortunate location of being side-by-side the Chesapeake Bay, Annapolis has long been a major seafood source for many a city and state. 

And as it has been passed on from its colonial origins, the seafood cuisine of Annapolis has also withstood the test of time. 

Although today’s restaurants may have each added their own personal twists or have incorporated the city’s modern or unique, personal influences, the seafood cuisine of Annapolis still stays true to its roots and remain hearty meals for its visitors and, of course, its people. 

Wanna have a bite of Annapolis seafood cuisine? Try out or get a table reservation at these fine restaurants in the city:

Price range: $$

Must-have menu item/s: steak & seafood combos

Price range: $$

The must-have menu item/s: crab cakes, lobster rolls, burgers

Price range: $$$

The must-have menu item/s: crab cakes, grilled oysters

As they say in Annapolis, the waterfront has been covered! (You’ve been told everything!) 

So, if you plan a trip to Annapolis anytime soon, check this out one more time in case you’ve forgotten to write anything on your to-do list. 

Happy sailing!