Guidebook for Annapolis

Penn
Guidebook for Annapolis

Food Scene

Family-owned Leeward Market and Cafe is at the end of our block and the jewel of Eastport! 7 am to 3 pm every day of the week. Fresh brewed coffee, made-to- order breakfasts and lunches, sandwiches to go, and our community gathering place!
It has a great set of views on the Naval Academy side of the Spa Creek and it hosts the Annapolis Water Taxi for a few bucks into Annapolis so you don't have to drive or walk, but the walk into Annapolis is easy and awesome!
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Chart House
300 Second St
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It has a great set of views on the Naval Academy side of the Spa Creek and it hosts the Annapolis Water Taxi for a few bucks into Annapolis so you don't have to drive or walk, but the walk into Annapolis is easy and awesome!
Great hidden fish market with outdoor restaurant tucked into this residential area is fabulous! Check it out! Take something home to cook or eat lunch there! Fresh fish daily! Others too!
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Wild Country Seafood
124 Bay Shore Ave
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Great hidden fish market with outdoor restaurant tucked into this residential area is fabulous! Check it out! Take something home to cook or eat lunch there! Fresh fish daily! Others too!
A great restaurant with a large bar area, that replays the Wednesday night race videos to incoming racers and hosts lots of music on Thursday nights. Great food. Sometimes a wait but there's a back bar. The Brunch is to die for. Not open for breakfasts. Parking is a bitch! So, if you stay at our place, JUST WALK!
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Boatyard Bar & Grill
400 Fourth St
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A great restaurant with a large bar area, that replays the Wednesday night race videos to incoming racers and hosts lots of music on Thursday nights. Great food. Sometimes a wait but there's a back bar. The Brunch is to die for. Not open for breakfasts. Parking is a bitch! So, if you stay at our place, JUST WALK!

Arts & Culture

We love the Maritime Museum which is on the same street we are on: Second. Public dock and outdoor education exhibit on the watermen who built Eastport and the Naval Academy. Hosts private functions and fundraisers.
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Annapolis Maritime Museum & Park
723 Second St
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Drinks & Nightlife

Open 7 days a week, including holidays, from 7 am to 3 pm, serving breakfast from eggs and bacon to bagels and muffins, to oatmeal. Kid friendly back room. Coffee is to die for. Go where the locals go!
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Leeward Market | Café & Grocery
601 Second St
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Open 7 days a week, including holidays, from 7 am to 3 pm, serving breakfast from eggs and bacon to bagels and muffins, to oatmeal. Kid friendly back room. Coffee is to die for. Go where the locals go!
Bar with great food! Davis's pub serves food until Midnight, but this is the sailors' sailor bar and local hangout. Ruddy and crowded sometimes, but with outdoor eating. Was featured on Diners and Dives for it's bagel crab melt! Great bar. Some games inside. Good for families and singles alike!
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Davis's Pub
400 Chester Ave
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Bar with great food! Davis's pub serves food until Midnight, but this is the sailors' sailor bar and local hangout. Ruddy and crowded sometimes, but with outdoor eating. Was featured on Diners and Dives for it's bagel crab melt! Great bar. Some games inside. Good for families and singles alike!