Support Us Button Widget

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-MD-sunset-Great-Escapes.jpg

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:

Annapolis-MD-pizza-Great-Escapes.jpg

You can’t beat pizza from Vin909.

Photo by RALtoday

Where to stay:

Bonus message from our partner: If you’re looking to book this trip, Scott’s Cheap Flights offers all the affordable flight hacks from your home airport. Sign up here.*

More from RALtoday
Sponsored
To help make your entire process at RDU as smooth as possible, we’ve created a guide that covers everything from gates and parking to details on the airport’s 48 nonstop routes.
Raleigh’s favorite indie rock fest is celebrating 15 years in downtown, and while you need a wristband to see the headliners + many club shows, you can still have plenty of fun without a ticket. Here’s how to enjoy Hopscotch without a wristband.
Dig into delicious and nutritious vegan and vegetarian fare in every corner of Raleigh.
From the floral backdrop to the customized ring — we’re dreaming of having our own viral engagement in Oak City.
The Pack is back in Carter-Finley on Thursday, Aug. 28 — here’s what you need to know while rooting for NC State football this season.
Bookmark this guide for a curated list of events taking place each month that we’re most looking forward to.
Have you ever thought “That’s an odd place for a bar.” Well in Raleigh, there is no such thing as odd for these spots around town.
After its March closure, a new team with ties to the former ownership group of 42nd Street Oyster Bar has expressed interest in reopening the Raleigh staple as early as February 2026. Read up on readers’ memories from this local gem.
Learn about the biggest industries and employers in Wake County with this guide to local business.