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Please check the FAQ page! It has been updated with bus seating instructions.
Please check the FAQ page! It has been updated with bus seating instructions.
July 17, 2021
Annapolis, MD

Ashley & Daniel

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    Things To Do

Things To Do

Annapolis is a drinking town with a sailing problem. For bars and restaurants, there are way too many to list in Downtown Annapolis. Here are our favorites:

Fox's Den

179B Main Street, Annapolis, MD 21401
, (443) 808-8991

We had our first date here. The pizza and cocktails here are amazing!

DRY 85

193 B Main Street, Annapolis, MD 21401
, (443) 214-5171

If you're a huge whiskey/bourbon fan, this is the place for you. Also, their truffle fries go great with everything they have here.

Red Red Wine Bar

189 B Main Street, Annapolis, MD 21401
, (410) 990-1144

Same owners as DRY 85. If you like wine more than whisky, this place is for you!

Rams Head Tavern

33 West Street, Annapolis, MD 21401
, (410) 268-4545

Your standard American gastro pub, but they have more than 100 beers to choose from due to their Around The World Beer challenge.

Level a small plates lounge

69 West Street, Annapolis, MD 21401
, (410) 268-0003

We came here to eat for our second date after the annual croquet match against St John's. Great selection of small plates to choose from.

Galway Bay Irish Restaurant and Pub

63 Maryland Avenue, Annapolis, MD 21401
, (410) 263-8333

Great if you're into Irish food and beer. Nice, calm atmosphere for those really late night drinks and conversations if you want to avoid the usual drinking scene in DTA.

Lemongrass

167 West Street, Annapolis, MD 21401
, (410) 280-0086

Amazing Thai food. This restaurant is attached to the rooftop bar Metropolitan.

The Red Bean

220 Main Street, Annapolis, MD 21401

This place serves soft serve ice cream mixed in with different toppings of your choice. They also sell great coffee and breakfast items to start your morning off right.

Annapolis Ice Cream Company

196 Main Street, Annapolis, MD 21401
, (443) 714-8674

Also known as the penguin ice cream shop. The ice cream is homemade every day. Dan's favorite flavor is apple pie.

Storm Bros. Ice Cream Factory

130 Dock Street, Annapolis, MD 21401
, (410) 263-3376

The ice cream here is also homemade daily. Ash's favorite flavor is rainbow sherbert.

Miss Shirley's Cafe, Annapolis

1 Park Place, Annapolis, MD 21401
, (410) 268-5171

One of the most popular breakfast spots in Annapolis. Expect a bit of a wait getting in on Sundays. If you like pancakes, waffles, or French toast this place is for you.

Buddy's Crabs & Ribs

100 Main Street, Annapolis, MD 21401
, (410) 626-1100

Another popular breakfast spot on Sundays. It's an all-you-can-eat brunch buffet that's perfect for hangovers.

Sofi's Crepes

1 Craig Street, Annapolis, MD 21401
, (410) 990-0929

Everything here is sold in a crepe (except drinks). Great for walking breakfast/lunch if you plan on exploring DTA or touring the Naval Academy.

Iron Rooster- Annapolis

12 Market Space, Annapolis, MD 21401
, (410) 990-1600

Also a popular breakfast spot on Sundays. They have giant homemade pop tarts (and I mean giant).

The Breakfast Shoppe

552 Ritchie Highway, Severna Park, MD 21146
, (410) 544-8599

Back for more B.S.

Capital SUP

7300 Edgewood Road, Annapolis, MD 21403
, (410) 919-9402

It's gonna be hot in July. If you're into calming outdoor watersports and see Annapolis along the Severn River and Chesapeake Bay, we highly recommend renting from this place. You may want to reserve a time slot with Capital SUP as this will be during peak tourist season.

Quiet Waters Park Road

Quiet Waters Park Road, Annapolis, MD 21403

Do you think nature is pretty neat? Check out this scenic park located along the water. You can rent paddleboards and kayaks here as well.

For all the days along the way
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