Things to do in Annapolis, MD

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    Thomas Point Lighthouse: A historic landmark in the Chesapeake Bay

    Photo courtesy of Gary Reich/iStock

Get Your Bearings in Annapolis

By Tawanna Browne Smith
Family Travel Expert

Stay
Eat
See & Do
Party
Shop

Where to Stay

Hotels in Annapolis are sprinkled throughout the city in popular areas such as near the Naval Academy and along West Street leading to the Capital, as well as the area around Westfield Annapolis mall. You'll find several big name brands within walking distance to major shopping and the waterfront, but you can also rest at a small bed and breakfast and Historic Inn near downtown hot spots as well.

Avoid:

Trying to book a hotel in the downtown area (if you don't have to) during the Annapolis Boat Show, Army-Navy football games and Naval Academy commencement.

What to Eat

Restaurants in Annapolis line West Street all the way from Route 50 down to the waterfront. For some of the best seafood eateries, cross Spa Creek and you'll stumble upon many of the Zagat-rated crew. Inside and across from Annapolis Town Center and Westfield Annapolis Mall are where the chain restaurants and many fast food eateries can be found.

Be Sure to Sample:

Crab cakes, fresh seafood.

Things to See

Annapolis attractions range from the historic to the ultra kid-friendly. The historic attractions can be found downtown near Church and Main Street. In the warmer months, cruises and boating activities are the attraction of choice for many locals. Tours and art galleries are sprinkled along West Street with more of the same along Main Street.

Take It or Leave It:

The new Seg tours in Annapolis are a fun way to see the city without doing too much walking.

Places to Party

Nightlife in Annapolis is pretty lively. You may find yourself hanging with a few midshipmen while you're checking out the local bar scene, adding to the character of your Navy-town experience. "Naptown," as the locals call it, has a small theater scene and live music in a host of venues ranging from small taverns to well-known spots like Rams Head on Stage, the sister location of Baltimore's Ram's Head Live!

Hot Tips:

To find who's playing any night of the week, check out the website for Annapolis's Visitors' Bureau.

Where to Shop

For a relatively small city, Annapolis has a nice selection of shopping options. If you're interested in the boutique stores with a picturesque, historic backdrop, then shopping along Main Street and the waterfront is where you want to be. If you're looking for an upscale mall experience, then Westfield Annapolis mall is your best bet. And if you're looking for a more open shopping center, then be sure to check out Annapolis Town Center, located about two miles up from the waterfront.

Avoid:

If you're going to Westfield Annapolis mall, avoid parking on the side of Cheesecake Factory and Nordstrom's. It can be a nightmare.

Hot Tips:

If you're looking for a fun, artsy, laidback shopping experience where a lot of locals go, check out West Annapolis.

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Annapolis is known for...

One of Annapolis's most unique features and characteristics.

1. An Officer and a Gentleman.:

The first thing people think of when they think about Annapolis is the Naval Academy and the young, well-dressed midshipmen that stroll the city streets in their sparkling clean bleach whites. Annapolis is a Navy town through and through, just as much as it's a boating town. The presence of the Naval Academy adds to the allure, excitement, and beauty of the city, especially when there's a football game or during graduation. Though, significantly more crowded, those are some of the best times to visit the city to get a real sense of its prestige and its history.