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.
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.
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.
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.
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!
To find who's playing any night of the week, check out the website for Annapolis's Visitors' Bureau.
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.
If you're going to Westfield Annapolis mall, avoid parking on the side of Cheesecake Factory and Nordstrom's. It can be a nightmare.
If you're looking for a fun, artsy, laidback shopping experience where a lot of locals go, check out West Annapolis.