Annapolis was a thriving, wealthy town in the 1600s and 1700s. Many of the houses and other buildings from the 1800s still remain, leaving a thriving, vibrant historic district with shops and restaurants along the waterfront. Brick-lined streets and quaint shops add to the feel. 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.
- Many major air carriers fly to Baltimore-Washington International Airport (BWI IATA), in Linthicum, Maryland, only a 30 minute drive from Downtown Annapolis.
- MTA Maryland. MTA Maryland operates rush-hour commuter bus service (Route 220 and Route 230) to Annapolis from Washington, D.C.; this service travels from Annapolis in the morning and to Annapolis in the afternoon and evening. A new commuter bus (Route 210) https://mta.maryland.gov/sites/default/files/Route210EffMar1-2017.pdf started in March 2017 that goes from Annapolis (and Kent Island) to downtown Baltimore in the morning and returns to Annapolis from Baltimore in the afternoon. They also operate local bus service (Route 14) to Annapolis from the Patapsco light rail station in Baltimore; this service operates all day.
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.
- The city put up a memorial at the waterfront of Alex Haley, author of the book "Roots" which became a TV mini-series in the mid 1970s. This memorial marks the spot where Kunta Kinte, first arrived in this country, in Annapolis in 1767. He came aboard a slave ship from Gambia, Africa named the Lord Ligonier.
- The United States Naval Academy is located here and has tours available. It's on Blake Road, in the heart of downtown, and you'll generally need to park outside of the "yard" and then enter on foot at the visitor center after an id check. 410-293-1000
- 1 Maryland State House, 100 State Cir, ☎ . 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.
- 2 Sandy Point State Park, 1100 East College Pkwy (19 km (12 mi) from central Annapolis, exit from US-50 just west of the Bay Bridge). Activities include swimming, fishing, crabbing, boating and windsurfing. The park's beaches and picnic areas provide views of the Chesapeake Bay Bridge. $4/person.
- 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. It's at the corner of Maryland Avenue and King George Street. Adults $10, children $5. Tours happen each hour from 12 to 4. Hours are 12-5, Tues-Sun, March–October, and last tour at 3 from November–February, 12-4, Tues-Sun. Hammond-Harwood House website.
- William Paca House. Is one of the most interesting historical home tours due to its fabulously restored gardens. It's on Prince George Street in between East Street and Maryland Avenue
- Visitors Center, 26 West St, toll-free: . 9AM-5PM daily. The official destination marketing organization of Annapolis & Anne Arundel County. Come in for area maps, restroom, restaurant menus, and tours and tour schedule.
- The Hall of Presidents Before Washington, The Westin Hotel- 100 Westgate Circle, e-mail: firstname.lastname@example.org. Open 24 hours a day, everyday. Free exhibit featuring 14 presidents before George Washington during Articles of Confederation from 1774 to 1789 in the Westin Hotel near the Annapolis waterfront. Free.
- 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. Schooner Woodwind website. 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 (website) 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 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 has enjoyed a Renaissance under Paul Johnson, and current coach Ken Niumatalolo. 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.
- 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.
- 1 Cantler's Riverside Inn, 458 Forest Beach Rd. 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. It's insanely hard to find by car, so either print out the directions from their website, or use a GPS navigation device.
- 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. On Main Street, just up from Church Circle. Joss Sushi website
- 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. 310 Third Street. O'Leary's Seafood website.
- 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 4 July and New Year's Eve. Try their Painkiller mixed drink, a locally famous one that will quickly put you in the mood. On Compromise Street, by the Marina. Pusser's website.
- Tsunami is home to delicious Asian and Indian food, known for their $5 lunch bowls. On the corner of West and Cathedral. Tsunami website.
- Pip's Dock Street Dogs is on Dock Street by Randall Street and has many different specialty hot dogs and sausages. It is good value and delicious. 410-990-9009
- Buddy's is located at the bottom of Main Street, by Market Space, and is home to good food with low prices. Watch out for specials like the $14.99 Main Lobster Feast. Buddy's website.
- 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. Sofi's Crepes website.
- Mangia is at the bottom of Main Street,by compromise on the circle and home to good Italian food and delicious pizza. 410-268-1350
- Maria's is on Market Space, on Market Space by Pinkney Street, and home to delicious Sicilian food, though it can be somewhat pricey. Maria's website.
- Osteria, 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. 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.
- 2 Heroes Pub, 1 Riverview Avenue, ☎ . A roast beef and brie here are a popular choice before a big NFL or Terrapin game. This place is often frequented by Terps fans to watch Terps and Duke basketball. Heroes also sponsors a very competitive Sunday Lacrosse league frequented by college recruiters.
- 3 Severn Inn, 1993 Baltimore Annapolis Blvd, ☎ . Best view in Annapolis, overlooking Severn River and U.S. Naval Academy. Great modern American Food. Wonderful wine list
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.
Annapolis is home to St. John's College (which also has a campus in Santa Fe). St. John's has an undergraduate and graduate studies programs in the Great Books tradition. All are welcome to attend the free, weekly lecture series  during the school year, or to visit the Greenfield Library. The school also hosts Great Books Saturday and a Continuing Education and Fine Arts program .
- 1 Hilton Garden Inn Annapolis, 305 Harry S. Truman Parkway, ☎ . Check-in: 3PM, check-out: 12PM. Located in the heart of Annapolis just 4 miles from the famous US Naval Academy and historic district. Available 24 hour fitness center, heated outdoor pool, and free WiFi. $109.
- 2 Annapolis Waterfront Hotel, 80 Compromise St, ☎ . The only accommodation located directly on the waterfront, in downtown Annapolis.
- 3 Historic Inns of Annapolis, 58 State Circle, ☎ , toll-free: . The Historic Inns of Annapolis in Maryland, with a historical restaurant, tavern, and rooms; this hotel is unforgettable.
- 6 Residence Inn by Marriott Annapolis, 170 Admiral Cochrane Drive, ☎ . Outside downtown Annapolis, but near shopping centers.
- 7 Annapolis Crowne Plaza, 173 Jennifer Road, ☎ , fax: . Annapolis Mall and Anne Arundel Medical Center.
- 8 SpringHill Suites Annapolis, 189 Admiral Cochrane Dr, ☎ , toll-free: . Conveniently located near Route 50.
- 9 The Westin Annapolis, 100 Westgate Circle, ☎ , fax: , e-mail: email@example.com. Check-in: 3PM, check-out: Noon.
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.
|Routes through Annapolis|
|Baltimore ← Glen Burnie ←||N S||→ END|
|Washington, D.C. ← Bowie ←||W E||→ Kent Island → Salisbury|
|Glasgow ← Kent Island ←||N S||→ Bowie → Richmond|