Dan’s Guidebook Annapolis
Food scene
Boatyard Bar & Grill
400 Fourth StLewnes' Steakhouse
401 Fourth StBest to make a reservation.
Main & Market
914 Bay Ridge RdGood Breakfast Spot - 5 min drive
Starbucks
1781 Forest Dr951 Bay Ridge Rd - closest Starbucks to the house.
Rocco's Pizzeria
954 Bay Ridge RdGreat Pizza to get delivered or bring in!
Harry Browne's Restaurant
66 State CirBest Wine & Pizza Place In Annapolis. They don’t take reservations, so get there early or plan on hanging out drinking wine for 45-90 minutes.
126 locals recommend
Vin 909 Winecafe
909 Bay Ridge AveBest Wine & Pizza Place In Annapolis. They don’t take reservations, so get there early or plan on hanging out drinking wine for 45-90 minutes.
Osteria 177
177 Main StGreat Restaurant, but you will want to make a reservation.
An Annapolis institution for over 50 years! Was featured on the show “Diners, Drive-Ins and Dives” and “Man vs Food” for their 6 lb
milk shake.
60 locals recommend
Chick & Ruth's Delly
165 Main StAn Annapolis institution for over 50 years! Was featured on the show “Diners, Drive-Ins and Dives” and “Man vs Food” for their 6 lb
milk shake.
Iron Rooster - Annapolis
12 Market SpaceAll Day Breakfast! Great comfort food.
Little Italy Annapolis
1411 Forest DriveSuper casual, but great spot for cheap eats with the family.
Best Italian Sandwiches in Town. If you stop in Parole MD, try Giolitti for lunch.
9 locals recommend
Giolitti Delicatessen
2068 Somerville RdBest Italian Sandwiches in Town. If you stop in Parole MD, try Giolitti for lunch.
Annapolis Ice Cream Company
196 Main St
Kilwins Chocolates & Ice Cream
212 King StreetCarrol's Creek Cafe
410 Severn AveBest spot on the water!
Family Friendly
Pirate Adventures on the Chesapeake
311 Third StQuiet Waters Park
600 Quiet Waters Park RdPennsylvania Dutch Farmer's Market
2472 Solomons Island RdSightseeing
US Naval Academy Museum
118 Maryland AveMaryland State House
100 State CirThere are plenty of boat tours to see this great Annapolis landmark.
10 locals recommend
Thomas Point Shoal Lighthouse
Thomas Point shoalThere are plenty of boat tours to see this great Annapolis landmark.
William Paca House & Garden
186 Prince George StColonial Annapolis Historic District
211 Main StMaryland World War II Memorial
1920 Governor Ritchie HighwayBefore you turn into Oyster Harbor, keep going straight until you dead end into Thomas Point.
12 locals recommend
Thomas Point Park
3890 Thomas Point RdBefore you turn into Oyster Harbor, keep going straight until you dead end into Thomas Point.
Things to Do
Catch a football game - stadium is very cool and definitely an experience to see Navy Play.
34 locals recommend
Navy-Marine Corps Memorial Stadium
550 Taylor AveCatch a football game - stadium is very cool and definitely an experience to see Navy Play.
Baltimore and Annapolis Trail
Baltimore and Annapolis TrailGreat Bike Trail
Sandy Point State Park
1100 E College Pkwy
Classic Sail Charters
980 Awald RoadAnnapolis Eventours offers unique and authentic day tours around Annapolis using all-electric, 5-passenger vehicles. They cover back streets, hidden gems and fascinating sights. Step into the lives of locals, find out what makes the city tick, and get acquainted with the local food, culture and history of Annapolis. A local, expert guide will lead you through a fantastic urban experience. Join us for our Explore the Heart of Annapolis history tour, or our Original Annapolis Seafood Crawl.
Urban Eventours
26 West StreetAnnapolis Eventours offers unique and authentic day tours around Annapolis using all-electric, 5-passenger vehicles. They cover back streets, hidden gems and fascinating sights. Step into the lives of locals, find out what makes the city tick, and get acquainted with the local food, culture and history of Annapolis. A local, expert guide will lead you through a fantastic urban experience. Join us for our Explore the Heart of Annapolis history tour, or our Original Annapolis Seafood Crawl.
Eastport
Great Restaurants, it’s a cute part of town.
Annapolis Towne Centre
1906 Towne Centre BlvdWatermark Tours, Charters, Cruises
1 Dock St130+ local and regional artists and crafters selling pottery, jewelry, wood turnings, clothes, furniture, blown and fused glass, photography, paintings and more. Plus cafe dining, food trucks and entertainment. Festivals are held on the first Sunday of each month from May to December 11am to 5pm. The event is pet friendly. Free Admission. 2 parking garages at the festivals on Calvert Street.
9 locals recommend
First Sunday Arts Festival
60 West St130+ local and regional artists and crafters selling pottery, jewelry, wood turnings, clothes, furniture, blown and fused glass, photography, paintings and more. Plus cafe dining, food trucks and entertainment. Festivals are held on the first Sunday of each month from May to December 11am to 5pm. The event is pet friendly. Free Admission. 2 parking garages at the festivals on Calvert Street.
https://fishingbooker.com/destinations/location/us/MD/annapolis
Search fishing booker and take a Chesapeake fishing trip. Make sure the Captain takes you to Thomas Point Lighthouse (historic landmark).
Annapolis Charter Fishing
1048 Turkey Point Roadhttps://fishingbooker.com/destinations/location/us/MD/annapolis
Search fishing booker and take a Chesapeake fishing trip. Make sure the Captain takes you to Thomas Point Lighthouse (historic landmark).
Traveler advice
Getting around
Uber or Lift - save yourself the trouble of parking.
Annapolis is very walkable, but parking can be challenging, try Uber or Lift to get to downtown.