Great Escapes: Our guide to Annapolis, MD

Planning a getaway? Check out Annapolis, MD, a historic city with small-town vibes surrounded by the Chesapeake Bay.


Annapolis sunsets are best by boat.

Photo by RALtoday

Planning a getaway? Check out Annapolis, MD — home to the US Naval Academy and a coastal destination with a vibrant downtown. A summer trip to Annapolis almost guarantees beautiful sunsets over the Bay + the best crabcakes you’ll ever try.

Why go?

  • Once the capital of the US and now the capital of Maryland, it’s hard to walk down the brick streets of Annapolis without running into a historically significant (and beautiful) building.
  • It’s easy to board a boat from downtown’s Ego Alley to explore local waterways.
  • During the Chesapeake Bay Paddle (Fri., Aug. 27 + Sat., Aug. 28), local and national paddlers will embark on an endurance challenge to protect the Bay.
  • Every summer, countless sailboats whir around downtown during the Annapolis Yacht Club’s Wednesday Night Race Series.
  • Check out the 2022 Annapolis Travel Guide for help planning your trip.

Act like a local:


You can’t beat pizza from Vin909.

Photo by RALtoday

Where to stay:

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