Coming to Annapolis for the night? Whether you’re meeting up with friends, planning a date with that special someone, or bringing the whole family, prepare for a great evening ahead. Here are just some popular ways to enjoy a night on the town in Annapolis. 

Indulge in dinner and drinks overlooking the water

There is no better backdrop to a romantic (or plain-old relaxing) evening than dining al fresco. Who can resist the sound of lapping water, the sight of sailboats gliding by as the sun sets, and the feel of a warm summer breeze? Some of Annapolis’ prime restaurants offer this incredible experience to patrons—plus the promise of a fresh taste of the Bay!

Blackwall Hitch Rooftop

Pub hop

Downtown Annapolis offers possibly one of the most inviting small-city pub scenes around. The easily walkable downtown area makes for convenient nightlife ambling in and out of a number of friendly pubs where locals and tourists mingle. Whether you are looking to share a recap of the latest local sailing regatta, listen to acoustic musicians in an intimate setting, or indulge in some tasty bar food and a few pints with friends, you’ll find the pub scene in Annapolis satisfying. 

Take a sunset cruise

To take in the view as you watch the sun dip below the horizon, there’s no better vantage point than the deck of a sailboat or yacht. Even better, you don’t have to own one to experience this perfect way to end the day in Annapolis. Sip a drink, snap pictures, or simply sit back and enjoy the view as an experienced captain takes you for an unforgettable sunset cruise. 

Enjoy an evening of classical music 

Many people associate Annapolis with history or sailing. But there’s much more: our classical music offerings are some of the finest in the region. The Annapolis Opera has been providing professional operas and concerts to Mid-Atlantic audiences for more than 40 years. A decade older than the Annapolis Opera, the Annapolis Symphony Orchestra features 70 professional musicians who perform symphonic music for audiences of all ages. 

Catch a play  

If you crave theater as part of your nighttime entertainment, Annapolis delivers—with a surprising number of choices. Looking for an intimate setting to watch Shakespeare performed by professional actors? Want to try a casual outdoor setting (in season) in the heart of downtown Annapolis to see a play? Interested in a dramatic presentation of one of your favorite classics? You’ll find these and more theatre options in Annapolis.