Annapolis has a thriving historic district with shops and restaurants along the waterfront. Most of the buildings are original 17th, 18th and 19th century, with brick lined streets. Tourism from the surrounding Baltimore and Washington, D.C. metro area is a major part of the town's life, as is a thriving boat business. One could easily spend a day walking around the town's downtown harbor area shopping and eating. There is also a lively nighttime scene.
MTA Maryland, . MTA Maryland operates rush-hour commuter bus service (routes 220  and 230 ) to Annapolis from Washington, D.C.; this service travels from Annapolis in the morning and to Annapolis in the afternoon and evening. They also operate local bus service (route 14 ) to Annapolis from the Patapsco light rail station in Baltimore; this service operates all day.edit
Annapolis Harbormaster (City Dock), 1 Dock Street, ☎ 410-263-7973 (firstname.lastname@example.org, fax: 410-295-9018), . Summer 8am-8pm; Winter 8am-4pm. Dock space and moorings are available on a first-come, first-serve basis. A Watch Commander is on duty and available by phone when the office is open; The Harbormaster can be contacted on VHF channel 09 or 17. City Dock has public spaces with wide slips and 30 & 50 amps service. Dock by the hour or day, depending on location. There are also docks available at St. Mary's Cove, Spa Creek, Back Creek, and others; the last two can get to City Dock using the water taxi service ($3+). Check-out time is 12 pm.edit
The first place you should stop in when you are in Annapolis is the Visitors Center, 26 West Street, 888-302-2852, 9AM-5PM, Monday through Sunday, the official destination marketing organization of Annapolis & Anne Arundel County. Come in for area maps, restroom, restaurant menus, and tours and tour schedule.
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. Though, the Annapolis Transit buses have a tendency to run off schedule and are often extremely early or extremely late; plan extra time if using the buses. Weekend nights, you will also find more than enough taxis available at the base of Main Street.
Annapolis City Dock (Ego Alley), 1 Dock Street, . A scenic marina on the Annapolis waterfront, good for walking, shopping, dining, and ship-watching. You can regularly see Naval Academy cadets here in uniform on the weekend, coming down to relax and with visiting friends. However you arrive, this is a central location to begin a walking tour of the downtown area.edit
Hammond-Harwood House is one of a series of historical homes open for tours. This treasure of a colonial mansion was designed by architect William Buckland and built in 1774. See colonial-era architecture and 18th century period furnishings including furniture produced by cabinet maker John Shaw, and paintings by portrait painter, Charles Willson Peale.
Kunta Kinte-Alex Haley Memorial, (next to Market House at City Dock), . 24/7. This public waterfront memorial of Alex Haley, author of the book "Roots," marks the spot where protagonist Kunta Kinte first arrived in this country in 1767. He came aboard a slave ship from Gambia, Africa, named the Lord Ligonier. "Roots" is notable as a 1970s TV mini-series as well as the biographical novel on which the series was based. It is comprised of a sculpture group, a wall, and a compass rose, located in the public plaza adjacent to Market House (25 Market St; aka Market Place Shopping Center) and at the innermost end of City Dock.(38.977639,-76.487032)edit
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 is 19 km (12 mi) from central Annapolis. Activities include swimming, fishing, crabbing, boating and windsurfing. The park's beaches and picnic areas provide views of the Chesapeake Bay Bridge. Admission per person starts at $4.
United States Naval Academy, Gate 1 (From City Dock, facing Market House, walk to the right up Randall St for 1 block to Prince George St. Pedestrian entrances are located a half block further on either Randall or Prince George.), ☎ 410-293-8687, . Daily, 9am-5pm. Located along the waterfront, and is a lovely walk as you visit the ship-building museum, crypt of John Paul Jones, and other sights on their grounds. As it is Navy property, access is restricted; plan to park in a public spot, and bring valid identification for anyone aged 16 and up. Tours are available through their Armet-Leftwich Visitors Center.edit
Visitors Center, 26 West Street, 888-302-2852, 9AM-5PM, M-Su, the official destination marketing organization of Annapolis & Anne Arundel County. Come in for area maps, restroom, restaurant menus, and tours and tour schedule.
William Paca House is one of the most interesting historical home tours due to its fabulously restored gardens.
The Treaty of Paris Center, 626C Admiral Drive #113, . 1st Saturday of the month from 11AM to 3PM. Treaty of Paris center that is open the first Saturday of each month from 11AM to 3PM at the Maryland Inn in Annapolis with historical documents, films and exhibits documenting the historical period from 1783 to 1787 before the Constitution was signed and Annapolis's role in the period as the capital of the US for a brief time.Free. edit
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.
Explore the historic district of Annapolis by foot. Walk with the colonial-clad guides of the Capital City Colonials  as they tour you about town explaining the history, buildings, and colonial life in Annapolis' golden age.
Lacrosse- Annapolis is generally considered to be the Lacrosse capital of the U.S., with marquee match-ups 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 has enjoyed a Renaissance under Paul Johnson, and current coach Ken Niumatalolo. Still, even in a good season, the mids and their chants can be more entertaining than the on-field activities. Although stadium seating is often available, families with kids are known to prefer the North end-zone, 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 march-on and for the weather-permitting flyovers.
Visit the Naval Academy. It is an interesting attraction.
Tour historic downtown Annapolis.
Visit the Maryland State House, the oldest continuously-operating State Capitol building in the United States.
Tour the Governor's Mansion.
Have some delicious Maryland Crabs and Crab cakes.
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. Many shops in downtown Annapolis tend to be fairly expensive and others cater to the tourists.
Westfield Annapolis Mall is on Bestgate Road and is the largest mall in the state and has a great selection.
Cantler's Riverside Inn, . 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. Try their soft crab sandwich, which is a whole crab with shell and an all but very soft and very delicious.
Joss Cafe. 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. Best sushi in town. Go to Nano's for Chinese food but stick to Joss for sushi.
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 harbor. Pusser's is also a prime spot to watch fireworks on 4th of July and New Year's Eve. Try their Painkiller mixed drink, a locally famous one that will quickly put you in the mood.
Tsunami on West Street, just of Church Circle is home to delicious Asian and Indian food, known for their $5 lunch bowls.
Pip's Dock Street Dogs is on Dock Street and has many different specialty hot dogs and sausages. It is good value and delicious.
Buddy's is located at the bottom of Main Street and is home to good food with low prices. Watch out for specials like the $14.99 Main Lobster Feast.
Sofi's Crepes is on Craig Street, close to the City Dock and home to delicious, fresh crepes made right in front of you. The selection is fairly large.
Mangia is at the bottom of Main Street, on the circle and home to good Italian food and delicious pizza.
Maria's is on Market Space, near the City Dock and home to delicious Sicilian food, though it can be somewhat pricey.
Osteria is on the corner of Main Street and Conduit Street. It is formal and fairly expensive. Wonderful food, beautiful atmosphere. Excellent bar with a world renowned bar tender.
Harry Browne's, 66 State Circle (directly across from the Maryland State House), ☎ 410-263-4332, . 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.edit
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.edit
Chick N' Ruth's. Located on main street, it is a family owned business which has been around for years. Breakfast all day, meals named after senators, magic shows in the mornings. There are pictures of everyone who has eaten there, from celebrities to presidents.edit
Sin Fronteras Cafe, 2129 Forest Drive, ☎ 410-266-0013, . Located in an unassuming strip mall next to a liquor store, this restaurant specializes in Mexican, Salvadorean, and Honduran cuisine.edit
Amsterdam Falafelshop, 25 Market Space (at City Dock), ☎ 410-268-1947, . A popular stop for people leaving the bars in Annapolis late at night, Amsterdam Falafelshop is known for serving falafel sandwiches in addition to a large toppings bar where customers can customize their sandwich.edit
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.
Severn Inn, 1993 Baltimore Annapolis Blvd, ☎ 410-349-4000. Best view in Annapolis, overlooking Severn River and U.S. Naval Academy. Great modern American Food. Wonderful wine listedit
Annapolis Marriott, ☎ 888-773-0786, . The only accommodation located directly on the waterfront, in downtown Annapolis.edit
Historic Inns of Annapolis, 58 State Circle, ☎ (410) 263-2641, Toll-free:1-800-847-8882, . The Historic Inns of Annapolis in Maryland, with a historical restaurant, tavern, and rooms; this hotel is unforgettable.edit
Loews Hotel Annapolis, 126 West Street, ☎ 410-263-7777, . The Loews Annapolis Hotel offers 198 spacious guestrooms, complimentary Wi-Fi, on-site restaurant and lounge, and meeting space in Downtown Annapolis.edit
Courtyard Annapolis, 2559 Riva Road, ☎ 1-410-266-1555, . checkin: 12PM; checkout: 3PM. A bit outside downtown Annapolis and near the US Naval Academy. $119. edit
O'Callaghan Hotel-Annapolis (Annapolis Hotel), 174 West Street, ☎ 410-263-7700, . checkin: 1:00PM; checkout: 12: PM. Settled in the heart of the Historic Annapolis, you will find a hotel that speaks of distant lands overseas. Hints of Ireland flow through the entryway and rooms with deep mahogany wood, marble and accents of European and Irish furnishings. The O’Callaghan Annapolis Hotel is a slow stroll away from the US Naval Academy, Maryland State House and of course the signature city dock lined with the masts of sailboats of all sizes.edit
Residence Inn by Marriott Annapolis, 170 Admiral Cochrane Drive, ☎ 410-573-0300, . Outside downtown Annapolis, but near shopping centers.edit
Sheraton Annapolis, 173 Jennifer Road, ☎ 1 410 266-3131 (fax: 1 410 266-6247), . Pet friendly hotel located near Annapolis Mall and Anne Arundel Medical Center.edit
SpringHill Suites Annapolis, ☎ 1-888-663-0094, . Conveniently located near Route 50.edit
The Inn at Spa Creek, 417 Severn Avenue, ☎ 410-263-8866, . Light, bright, contemporary B & B in the maritime section of Annapolis, within walking distance of all historic attractions.edit
The Westin Annapolis, 100 Westgate Circle, ☎ 1-410-972-4300 (email@example.com, fax: 410-295-7420), . checkin: 3PM; checkout: Noon. Newly opened in July 2007.edit
DoubleTree by Hilton Hotel Annapolis, 210 Holiday Court, Annapolis, Maryland, 21401, USA, ☎ 1-410-224-3150, . checkin: 4:00 PM; checkout: 12:00 PM. Full service hotel just a short walk from Annapolis Towne Centre featuring complimentary WiFi throughout the hotel, an onsite restaurant and bar, business center, fitness center, and much more.edit
Annapolis is one of the safest cities in Maryland. The normal precautions apply, but downtown is pretty much safe at all times. Due to its status as the state capital, there is a larger-than-usual police presence; the Annapolis City Police, Maryland Capital Police, Maryland State Police and, Anne Arundel County Police are all commonly seen in the city and surrounding areas.
The Chesapeake Bay Bridge is close, and when it was built it was the largest bridge of its type in the world. The western end is at Sandy Point State Park which has great views of the bridge and bay and ships passing on the way to Baltimore. From here you can see the Baltimore Lighthouse which for a brief time in the 1960s was the world's first and only nuclear powered lighthouse (it is solar powered at this time). Kite flying, beach walking, swimming, summer concerts, boat launches, etc.. are all here. At the other end of the bridge is Kent Island, another historic place, known for its seafood and popular new bike trails.
This is a usable article. It has information for getting in as well as some complete entries for restaurants and hotels. An adventurous person could use this article, but please plunge forward and help it grow!