• Annapolis is the sailing capital of the United States (there's a sign saying so right before the Eastport Bridge), so you must go sailing while in Annapolis. The easiest way is to take a 2 hour cruise aboard the Schooner Woodwind which departs a few times daily from the dock at the Marriott Hotel. You can raise the sails, take the helm, watch for crab pots, see the sunset and experience Annapolis from the water. Beer, wine and soft drinks are available. Feel free to bring your lunch. And bring a camera, a good hat and soft-soled shoes.
• Another great thing to do is go to Sandy Point State Park and look at the Chesapeake Bay Bridge. It provides spectacular views and also a view of an old lighthouse in the middle of the Chesapeake.

• Lacrosse- Annapolis is generally considered to be the Lacrosse capital of the U.S., with marquee matchups between high school powers St. Mary's and Severn taking place in the spring at the United States Naval Academy. Numerous nationally recognized junior and club teams also play throughout the year.

• Scenic Drives- Although Marylanders love the Chesapeake Bay, the majority of waterfront property is privately owned. As a result, very few scenic drives exist in Annapolis. The closest thing to an open drive is through Bay Ridge at the end of Forest Drive.

• Navy Football- Although largely dormant since Roger Staubach's days, Navy football is enjoying a Renaissance under Paul Johnson. Still, even in a good season, the middies and their chants can be more entertaining than the onfield activities. Although stadium seating is often available, families with kids are known to prefer the North endzone, which is a grassy hill. The list of battles in which USNA alumni participated is always impressive, and leaves a strong impression. Be sure to be inside the stadium for marchon and for the weather permitting flyovers.

• The city recently put up a memorial at the waterfront marking the spot where Kunta Kinte the African from the book/movie "Roots" arrived aboard a slave ship.
• The United States Naval Academy is located here and has tours available.
• The Maryland State House was the capitol of the United States from November 26, 1783 to August 13, 1784. In that State House, oldest in the nation still in legislative use, General George Washington resigned his commission before the Continental Congress. There, on January 14, 1784, Congress ratified the Treaty of Paris to end the Revolutionary War. From there, the Annapolis convention issued the call to the states that led to the Constitutional Convention.
• Sandy point state park.
• Hammond-Harwood House is one of a series of historical homes open for tours. See colonial-era architecture and 17th century period furnishings.
• William Paca House is one of the most interesting historical home tours due to its fabulously restored gardens.

• From Baltimore, take I-97 south then go east on Hwy 50.
• From Washington, D.C., take Hwy 50 East.

The most economic way of enjoying Annapolis would be getting around on foot. There are plenty of parking spaces available during less crowded times, such as during the winter months and weekdays after work hours. They are easy to find by following either the parking signs to a parking garage or looking around the harbor area for metered spots which can be held for up to two hours. Bicycles are also an option to bring along, but generally wouldn't be needed for a day of sightseeing in the harbor area.

Tourist maps are available at many downtown establishments, usually highlighting map sponsors as places to visit, but also including most places of interest as a not-to-scale reference. Any local Annapolitan would be more than happy to give short directions, or even a tip on where to eat.

During the busier times, a parking place will be a bit harder to find, but patience is usually rewarded. If needing extended transport, a bus line does traverse Annapolis at various locations. Weekend nights, you will also find more than enough taxis available at the base of Main Street.

There are many, many shops catering to all tastes in historic downtown Annapolis and it is very easy to just take a stroll and look around at what there is to see.

• Cantler's Riverside Inn, [1]. One of the best seafood restaurants in the area. About 15 minutes outside of town nestled on the backwaters of the Chesapeake Bay. You can arrive by boat or car. Cantler's is an authentic Maryland Family Style seafood restaurant where you sit at park benches and eat shoulder to shoulder with everyone. Steamed crabs are a favorite but so are lots of local, freshly-caught seafood choices. Cantler's is an Annapolis family-run institution.

• Yin Yankee Cafe, [2]. A decent Asian/American fusion cafe right in the heart of downtown Annapolis at the foot of Main Street. Traditional and nouveau sushi are both excellent. Excellent vegetarian/vegan cuisine available here. A tourist spot where it is nice to sit outside, or admire the fish tanks and amazing fish displays on the inside. Also has a solid menu for with somewhat more traditional fare. The fish and chicken sandwich both are excellent.

• Joss. The "in the know" sushi spot in Annapolis. Small, generally crowded and no reservations available. Located towards the top of Main Street on the left.

• O'Leary's Seafood in Eastport is by far the best seafood restaurant in the area. It is consistently ranked as one of the Washington, DC area's top 100 restaurants.

• Pusser's is right on the water, and a great place to get a couple of drinks on the harbour. Pusser's is also a prime spot to watch fireworks on 4th of July and New Year's Eve.

• Harry Browne's- The place for Annapolis insiders on State Circle. Often frequented by visiting politicians, a tourist shouldn't let the minor celebritology stand in the way of what is Annapolis's finest restaurant. The bar upstairs is known for excellent martinis, and often gets very crowded around 11pm. Perhaps the best place for cigars until the cigar ban goes into effect.

• Heroes Pub- (Off of Ridgely Road) by St. John Neummann Church. A roast beef and brie are ideal before a big NFL or Terrapin game. THE place for local Terps fans to watch Terps and Duke basketball. Heroes also sponsors a very competitive Sunday Lacrosse league frequented by college recruiters.

Along with a lively night scene, there comes a number of great bars. During the day most of these play the role of family restaurant very well and serve outstanding authentic Maryland food and then turn up the volume when the sun goes down. It can be a bit odd to travelers having lunch at a great restaurant that happens to serve some drinks and hoping to be back for dinner, only to find a packed bar that happens to serve some food.

There are far too many to name, even in a small downtown such as Annapolis, but one unique specialty can be found at Lujan's Pub. Situated on the water front it caters to mostly Naval Academy Midshipmen but finds its fan base with the tourist. Ask for the Crab Cod. A delicious mix of crab juice with rum and cherry flavors. Other main street establishments can lead to an interesting interaction between the very rich and the Middies.

The Mexican Cafe on the south side of town remains very popular for those visiting PAL Park.