Annapolis Travel Guide

USA  #9 in Best Cheap Summer Vacations
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What to Eat in Annapolis

Owing to its idyllic perch on the harbor, you might guess that dining in Annapolis would be seafood-heavy. And you'd be right. Steamed crabs, in particular, are one of the city's specialties, and you can try them at any number of restaurants. Mike's Crab House and Cantler's are among some of the old favorites. For ice cream, the Annapolis Ice Cream Company is an unparalleled spot. If you're looking for a wine bar, you might try the well-reviewed Vin 909 Winecafe. Chick & Ruth's Delly is legendary, namely for their "colossal challenges," which involve downing a 6-pound milkshake or munching your way through a 3-pound sandwich. 

Find the Best Restaurants in Annapolis

  • #1
    Vin 909 Winecafe
    #1 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 701 reviewsTripAdvisor (701)
    $ - $$ | American, Pizza, Wine Bar
    909 Bay Ridge Ave, Annapolis, MD 21403-3029
    Read More »
  • #2
    Annapolis Ice Cream Company
    #2 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 764 reviewsTripAdvisor (764)
    $ | American
    196 Main St, Annapolis, MD 21401
    Read More »
  • #3
    Dry 85
    #3 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 237 reviewsTripAdvisor (237)
    $ - $$ | American, Bar, Pub
    193B Main St, Annapolis, MD 21401-2006
    Read More »
  • #4
    Osteria 177
    #4 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 548 reviewsTripAdvisor (548)
    $$ | Italian, Seafood
    177 Main St, Annapolis, MD 21401-2006
    Read More »
  • #5
    Kilwins
    #5 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 221 reviewsTripAdvisor (221)
    $ | American
    128 Main St, Annapolis, MD 21401-2003
    Read More »
  • #6
    Sofi's Crepes
    #6 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 223 reviewsTripAdvisor (223)
    $ | Cafe
    1 Craig St, Annapolis, MD 21401-1801
    Read More »
  • #7
    O'Leary's Seafood Restaurant
    #7 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 437 reviewsTripAdvisor (437)
    $$ | American, Seafood, Contemporary
    310 Third St Eastport, Annapolis, MD 21403-2510
    Read More »
  • #8
    Light House Bistro
    #8 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 99 reviewsTripAdvisor (99)
    $ - $$ | American, Bar, Cafe
    202 West Street, Annapolis, MD 21401
    Read More »
  • #9
    Boatyard Bar & Grill
    #9 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 1710 reviewsTripAdvisor (1710)
    $ - $$ | American, Bar, Seafood
    400 4th St, Annapolis, MD 21403-2504
    Read More »
  • #10
    Iron Rooster Annapolis
    #10 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 1368 reviewsTripAdvisor (1368)
    $ - $$ | American, Bar
    12 Market Space, Annapolis, MD 21401-1816
    Read More »
  • #11
    Jalapeno's
    #11 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 540 reviewsTripAdvisor (540)
    $ - $$ | Mexican, Latin, Spanish
    85 Forest Drive Forest Plaza, Annapolis, MD 21401-3716
    Read More »
  • #12
    Miss Shirley's Cafe, Annapolis
    #12 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 693 reviewsTripAdvisor (693)
    $ - $$ | American, Cafe
    1 Park Pl, Annapolis, MD 21401-3475
    Read More »
  • #13
    Lewnes'
    #13 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 451 reviewsTripAdvisor (451)
    $$ | American, Steakhouse
    401 4th St, Annapolis, MD 21403-2503
    Read More »
  • #14
    Mason's Famous Lobster Rolls
    #14 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 302 reviewsTripAdvisor (302)
    $ - $$ | American, Seafood, Fast Food
    188 Main St, Annapolis, MD 21401-2008
    Read More »
  • #15
    Davis Pub
    #15 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 280 reviewsTripAdvisor (280)
    $ - $$ | American, Bar, Pub
    400 Chester Ave, Annapolis, MD 21403-3205
    Read More »
  • #16
    Preserve
    #16 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 209 reviewsTripAdvisor (209)
    $ - $$ | American
    164 Main St, Annapolis, MD 21401-2007
    Read More »
  • #17
    Galway Bay
    #17 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 761 reviewsTripAdvisor (761)
    $ - $$ | American, Irish, Bar, Pub
    63 Maryland Ave, Annapolis, MD 21401-1629
    Read More »
  • #18
    Carrol's Creek Cafe
    #18 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 1405 reviewsTripAdvisor (1405)
    $ - $$ | American, Seafood
    410 Severn Ave, Annapolis, MD 21403-2524
    Read More »
  • #19
    Dock Street Bar & Grill
    #19 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 364 reviewsTripAdvisor (364)
    $ - $$ | American, Bar, Seafood, Pub, Gastropub
    136 Dock St, Annapolis, MD 21401-1803
    Read More »
  • #20
    Level a small plates lounge
    #20 of 418 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 365 reviewsTripAdvisor (365)
    $ - $$ | American, Bar, Pub
    69 West St, Annapolis, MD 21401-2426
    Read More »

Explore More of Annapolis

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