$$ - Breakfast or Lunch Hip spot with views of Ego Alley serving a creative, all-day breakfast menu & American comfort food.
$$ - Breakfast or Lunch Voted Maryland's Favorite Restaurant. As seen on Food Network's Diners, Drive-Ins and Dives
$ - Breakfast or Lunch Lively landmark diner for over 50 years in the heart of Annapolis, featuring greasy-spoon breakfasts, piled-high sandwiches, and award winning crab cakes!
$ - Breakfast or Lunch About a mile from downtown, but worth it for their amazing breakfast bagels.
$$ - Food & Drinks A chic, bohemian haunt focused on coastal cuisine with eclectic small & large plates, and hand tossed pizzas. Savor 35+ Wines by the Glass, Flights, 120+ Wines by the Bottle with a full bar.
$$ - Food & Drinks Casual eatery in historic downtown offering New American tavern fare & shaded outdoor tables.
$$ - Food & Drinks Long-standing (since 1975) tavern offering dozens of craft beers plus a raw bar & pub-fare menu.
$$ - Food & Drinks Casual restaurant with a broad American menu & full bar plus rooftop deck & local live music.
$$ - Food & Drinks Intimate nook with 1920s flair offering bourbon & beer, plus refined takes on American comfort food.
$$ - Food & Drinks Relaxed, rustic-chic locale emphasizing locally-sourced small plates, gourmet pizzas & craft beer.
$$$ - Dinner Acqua al 2's brings the same authentic Tuscan cuisine you would find in it's home city of Florence, Italy. They provide a wide array of vegetarian pastas, hand-carved steaks, and fresh seafood. | Reservations Encouraged |
$$$ - Dinner Blackwall Hitch is a coastally inspired restaurant featuring upscale fare, plus innovative cocktails & an extensive wine list. Haley was a waitress here for 3 summers in college.
$$ - Drinks Harold Black is a warm, intimate bar that offers a range of house and custom cocktail options. Harold Black serves a light-fare menu with a selection of cured meats, cheeses and desserts. | Reservations Encouraged |
$$ - Drinks Parley Room is a sophisticated 30-seat 1920s-era-style cocktail bar located in Downtown Annapolis. While it is a small/intimate cocktail bar, the drinks are fantastic.
$$ - Drinks Classic waterside restaurant specializing in Caribbean food & rum-based cocktails. We primarily recommend enjoying a drink on their outside patio right on the water!
$ - Brewery The city’s first nanobrewery, Forward Brewing is a must-visit spot in Eastport for beer lovers. Haley's long time friend, and former roommate Zoe is a manager here!
Although a stroll downtown gives you a great taste of Annapolis, the capital city is so much more than that. To gain a greater appreciation for all this cute place has to offer, hop on a trolley tour.
Haley loves to shop so we had to throw this in. Main street offers a variety of unique boutiques, shops, and galleries you can browse to your heart’s content.
One of the most enjoyable Annapolis activities is to appreciate the beautiful Severn River and Chesapeake Bay on a cruise. Two of the most popular ways to get out on the water are on the Harbor Queen or the Schooner Woodwind. https://www.schoonerwoodwind.com/ https://watermarkjourney.com/public-cruises-water-taxi/annapolis-cruises/
One of the most popular things to see in Annapolis is the US Naval Academy. On a 90-minute tour, guides take you to some of the main sites on the campus of this National Historic Site. Haley's Grandfather, Father, Uncle, and Cousin all attended the Naval Academy.