Andrea’s Annapolis guidebook
Food scene
Main Street / City Dock station
Great food. Great views from balcony seating, a great facility, and the best happy hour around ! Parking available for free (ticket validated inside)
81 locals recommend
Carrol's Creek Cafe
410 Severn AveGreat food. Great views from balcony seating, a great facility, and the best happy hour around ! Parking available for free (ticket validated inside)
Not your average pizza place. Here you will find sumptuous food, great wine, and great people! This unique place does not accept reservations but you can always call to get an idea of how long the line is. Parking available with overflow parking on the street.
126 locals recommend
Vin 909 Winecafe
909 Bay Ridge AveNot your average pizza place. Here you will find sumptuous food, great wine, and great people! This unique place does not accept reservations but you can always call to get an idea of how long the line is. Parking available with overflow parking on the street.
A pickled food concept on historic mainstreet where everything tastes amazing. Great urban rustic decor
38 locals recommend
Preserve
164 Main StA pickled food concept on historic mainstreet where everything tastes amazing. Great urban rustic decor
This is a long time local favorite in historic eastport. Nautical themed. Parking available on site.
127 locals recommend
Boatyard Bar & Grill
400 Fourth StThis is a long time local favorite in historic eastport. Nautical themed. Parking available on site.
This place has been an Annapolis staple for a long long time. Stop by late night when you are running out of options and this place will be open and ready to serve with a fantastic crabcake and burger. Huge menu here !
60 locals recommend
Chick & Ruth's Delly
165 Main StThis place has been an Annapolis staple for a long long time. Stop by late night when you are running out of options and this place will be open and ready to serve with a fantastic crabcake and burger. Huge menu here !
A modern taco place that sells drinks too. On main st with a great vibe.
39 locals recommend
Vida Taco Bar
200 Main StA modern taco place that sells drinks too. On main st with a great vibe.
Annapolis Smokehouse And Tavern
107 Hillsmere DrSoul
509 S Cherry Grove AveRed Red Wine Bar
189 B Main StCafé Normandie
185 Main StCooper's Hawk Winery & Restaurant
1906 Towne Centre BoulevardChart House
300 Second StSam's on the Waterfront
2020 Chesapeake Harbour Drive EastNeighborhoods
Eastport is a walkable neighborhood with great restaurants. From Eastport, walk across the bridge to historic Annapolis to enjoy the views of the old city and its many sailboats.
34 locals recommend
Eastport
Eastport is a walkable neighborhood with great restaurants. From Eastport, walk across the bridge to historic Annapolis to enjoy the views of the old city and its many sailboats.
Sightseeing
Annapolis Canoe and Kayak, LLC
311 Third StKayak rentals and sales !
Thomas Point Shoal Lighthouse
Thomas Point shoalUS Naval Academy Museum
118 Maryland AveLive Music
A great local place that hosts local artists. Good food too.
22 locals recommend
49 West Coffeehouse, Winebar & Gallery
49 West StA great local place that hosts local artists. Good food too.
Recreation
Kayaking, boating, trails, fishing, beaches, etc...
For a small fee, you can try out larger hobie sailing kayaks and other boats like the latest Adventure Island while also experiencing the waters of downtown annapolis !
Backyard Boats, Dinghy & Small Water Craft Specialists
222 Severn AveFor a small fee, you can try out larger hobie sailing kayaks and other boats like the latest Adventure Island while also experiencing the waters of downtown annapolis !
Quiet Waters Park
600 Quiet Waters Park RdThomas Point Park
3890 Thomas Point RdTraveler advice
Don't miss
The Dutch PA farmers market is as authentic as it gets.
There is even a simple restaurant within the market that sells old fashioned breakfast.
Getting around
Conveniently park along main street or at the harbor lot
Parking is generally easy at the harbor dock parking lot, along main street, or along neighborhood side streets. Special events may make parking more challenging.
Don't miss
Walk up and down Main street and to the harbor dock
Brick paved roads and Annapolis flair. Yacht watching is always fun. If you are lucky, you may experience a live street music performer or two.