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Frequently Asked Questions

Below are answers to many of the questions we hear most often. If you have any additional questions, please feel free to contact us; we will be sure to assist you! We look forward to welcoming you at The Annapolis Inn.


We experience a range of seasons here in Annapolis. Take a look at the average temperatures so you can pack accordingly and make sure to check the weather before you leave.

Here is our parking in Annapolis page to guide you. 

We are in Downtown Annapolis close to all the shops and attractions!


See all of your transportation options, and taking the trolly is highly recommended!

Yes! There are many popular biking trails in the area.


Here are some of our favorite ways to spend time on the water:

  • Canoeing and kayaking
  • Wind and kite surfing
  • Paddleboarding
  • Charter a boat
  • Sailing school

The Naval Academy is a beautiful place to walk, attend football games, and watch the famous regattas sail by. See more things to do at the Naval Academy.

The Annapolis Inn is just one block from the Naval Academy.

St. John’s College is an esteemed liberal arts college in Annapolis with a well-manicured campus to tour and the famed annual croquet match against the Naval Academy, known as “the purest intercollegiate athletic event in America” according to GQ.

When is the Croquet Match in Annapolis?

The Annapolis Cup is held every spring. See this year’s dates.

Yes. Enjoy a romantic meal downtown or shop at charming boutiques.

Directory of downtown shops

Shopping experiences

One of our favorite places to get fresh crab is Cantlers, a waterfront restaurant by the docks. 


  • Flowers by Donna
  • Michael Designs Florist
  • St. Anne’s Parish
  • St. Mary’s Church
  • First Presbyterian Church of Annapolis
  • Calvary Memorial Baptist Church
  • USNA Chapel