5 Day Restaurant Itinerary for Annapolis, MD

Eat your way through Annapolis, MD like you are Guy Fieri or another Food Network host with our curated list of restaurants seen on popular TV shows like Diner's Drive-Ins and Dives and 50+ other FoodTV shows.

You can also use our AI Restaurant Concierge to further refine your plans or just explore more restaurants on TV.

Trip Itineraries for Annapolis, MD:

1 Day TripWeekend Trip5 Day Trip

Day 1

Breakfast

Restaurant: Chick & Ruth's Delly

Show: Man vs Food

Known For: 6 pound 'Colossal' milkshake and a 1.5-pound cold cut 'Colossal' sandwich or 1-pound hamburger with a one-hour time limit for completion

Chick & Ruth's Delly

Lunch

Restaurant: Davis's Pub

Show: Diners, Drive-ins and Dives

Known For: The sidewalk shack worth stopping for, with dishes like chipotle habanero barbecue pork sandwiches

Davis's Pub

Dinner

Restaurant: Galway Bay Irish Restaurant and Pub

Show: Diners, Drive-ins and Dives

Known For: Two Irish brothers servin' up food from their homeland with a twist, like Guinness fried oysters with homemade coleslaw

Galway Bay Irish Restaurant and Pub

Day 2

Breakfast

Restaurant: Miss Shirley's Cafe, Inner Harbor

Show: Diners, Drive-ins and Dives

Known For: Breakfast/Lunch specialities like coconut cream french toast and crab cake po boys

Miss Shirley's Cafe, Inner Harbor

Lunch

Restaurant: Boatyard Bar & Grill

Show: Food Paradise

Known For: Crab cake sandwich

Boatyard Bar & Grill

Dinner

Restaurant: Joss Café & Sushi Bar

Show: Best Thing I Ever Ate

Known For: Fried Shrimp Heads

Joss Café & Sushi Bar

Day 3

Breakfast

Restaurant: Blue Moon Cafe

Show: Diners, Drive-ins and Dives

Known For: Sweet Baby Jesus

Blue Moon Cafe

Lunch

Restaurant: Pierpoint Restaurant

Show: Best Thing I Ever Ate

Known For: Crab Cakes

Pierpoint Restaurant

Dinner

Restaurant: Alewife Baltimore

Show: Diners, Drive-ins and Dives

Known For: Beer bar with some great dishes like pork belly mac n cheese and boar sliders

Alewife Baltimore

Day 4

Breakfast

Restaurant: Broadway Diner

Show: Diners, Drive-ins and Dives

Known For: Steak, Italian, Sandwiches, American, Diner

Broadway Diner

Lunch

Restaurant: G & A Restaurant

Show: Diners, Drive-ins and Dives

Known For: Italian, Hot Dogs, American, Burgers, Traditional

G & A Restaurant

Dinner

Restaurant: Charleston

Show: Best Thing I Ever Ate

Known For: Burgundy Snails

Charleston

Day 5

Breakfast

Restaurant: Sip & Bite Restaurant

Show: Diners, Drive-ins and Dives

Known For: Greek spot where two cooking families come together to serve up age-old family recipes

Sip & Bite Restaurant

Lunch

Restaurant: Jimmy's Famous Seafood

Show: Diners, Drive-ins and Dives

Known For: Local legendary place making amazing crab and other seafood dishes

Jimmy's Famous Seafood

Dinner

Restaurant: Mo's Seafood

Show: No Reservations

Known For: Tony eats here with Felicia (Snoop) Pearson from The Wire. This is one of her favorite restaurants.

Mo's Seafood
Reminder: These plans are AI generated for your convenience. Please review them before planning a trip around them.