Guidebook for Annapolis
Sightseeing
Open to the Public. Highly suggest attending either the 9AM or the 11AM Sunday Service
The historic Chapel at the center of the Yard. Enter Via Maryland Avenue.
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USNA Chapel
121 Blake RdOpen to the Public. Highly suggest attending either the 9AM or the 11AM Sunday Service
The historic Chapel at the center of the Yard. Enter Via Maryland Avenue.
Located at 723 Second Street, in the neighborhood of Eastport, just “across the creek” from USNA & City Dock. Designed to educate visitors of all ages about Annapolis’s rich maritime heritage.
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Annapolis Maritime Museum & Park
723 Second StLocated at 723 Second Street, in the neighborhood of Eastport, just “across the creek” from USNA & City Dock. Designed to educate visitors of all ages about Annapolis’s rich maritime heritage.
Two beautiful, wooden, 74-foot schooners, Woodwind & Woodwind II, for a true sailing experience.
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Schooner Woodwind Sailing Cruises
80 Compromise StTwo beautiful, wooden, 74-foot schooners, Woodwind & Woodwind II, for a true sailing experience.
The William Paca House is an 18th-century Georgian mansion. William Paca was a signatory of the Declaration of Independence and a three-term Governor of Maryland.
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William Paca House & Garden
186 Prince George StThe William Paca House is an 18th-century Georgian mansion. William Paca was a signatory of the Declaration of Independence and a three-term Governor of Maryland.
Segs In The City
232 West StGuided Segway Tours & Rentals in Historic Downtown Annapolis
Guided Tours & Kayak Rentals. Kayak through one of America’s oldest seaports, the Annapolis harbor with the United States Naval Academy as the backdrop.
Kayak Annapolis LLC
900 Truxtun Park RdGuided Tours & Kayak Rentals. Kayak through one of America’s oldest seaports, the Annapolis harbor with the United States Naval Academy as the backdrop.
Drinks & Nightlife
VOTED BEST WINE BAR - Best of Annapolis. Excellent food, wine selection & service. Located on Main Street in Downtown Annapolis
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Red Red Wine Bar
189 B Main StVOTED BEST WINE BAR - Best of Annapolis. Excellent food, wine selection & service. Located on Main Street in Downtown Annapolis
Superior Food, Bourban, Libations & Service. Casual/Cozy Atomosphere.
193 Main St in Downtown Annapolis.
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DRY 85
193 B Main StSuperior Food, Bourban, Libations & Service. Casual/Cozy Atomosphere.
193 Main St in Downtown Annapolis.
Food Scene
Excellent Up-Scale Italian. Elegant Atmosphere. Wonderful Food. Excellent Service.
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Osteria 177
177 Main StExcellent Up-Scale Italian. Elegant Atmosphere. Wonderful Food. Excellent Service.
The Boatyard is where local sailors, fishermen and lovers of the Chesapeake enjoy pint drinks, great crab cakes and the freshest local seafood. Washingtonian Magazine calls it "...the nautical Cheers"
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Boatyard Bar & Grill
400 Fourth StThe Boatyard is where local sailors, fishermen and lovers of the Chesapeake enjoy pint drinks, great crab cakes and the freshest local seafood. Washingtonian Magazine calls it "...the nautical Cheers"
An Annapolis institution since 1975, this dockside eatery & watering hole is full of good cheer, great drink, &grand food. A heritage of seasonal shell-and fish dishes, the finest burgers & raw bar!
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McGarvey's Saloon & Oyster Bar
8 Market SpaceAn Annapolis institution since 1975, this dockside eatery & watering hole is full of good cheer, great drink, &grand food. A heritage of seasonal shell-and fish dishes, the finest burgers & raw bar!
Voted "100 Very Best Restaurants" By Washingtonian Magazine. "Don’t miss: Crab rolls; poached shrimp with fennel rémoulade; house-made burrata; crab gumbo; Margherita pizza; butterscotch pudding"
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Vin 909 Winecafe
909 Bay Ridge AveVoted "100 Very Best Restaurants" By Washingtonian Magazine. "Don’t miss: Crab rolls; poached shrimp with fennel rémoulade; house-made burrata; crab gumbo; Margherita pizza; butterscotch pudding"
Downtown's Newest HOT SPOT! Serving a new twist on traditional comfort food, including breakfast all day, lunch, supper & drinks.
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Iron Rooster - Annapolis
12 Market SpaceDowntown's Newest HOT SPOT! Serving a new twist on traditional comfort food, including breakfast all day, lunch, supper & drinks.
Washington Post says "casual spot that offers a rarity in downtown Annapolis, waterfront dining ... with a hint of Caribbean on the Chesapeake Bay. It's a place for top-siders & rum drinks & music"
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise StWashington Post says "casual spot that offers a rarity in downtown Annapolis, waterfront dining ... with a hint of Caribbean on the Chesapeake Bay. It's a place for top-siders & rum drinks & music"
Everything Else
Hop on a taxi and visit your favorite restaurant or get from Downtown to Eastport easy. No need to worry about finding a parking spot when you travel via Water Taxi. CALL 410.263.0063
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Baltimore Water Taxi
901 S BroadwayHop on a taxi and visit your favorite restaurant or get from Downtown to Eastport easy. No need to worry about finding a parking spot when you travel via Water Taxi. CALL 410.263.0063
Arts & Culture
LIVE MUSIC VENUE in DOWNTOWN ANNAPOLIS.
Brick-walled tavern with a wisteria-covered heated patio serving pub fare & regional seafood dishes.
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Rams Head Tavern Annapolis
33 West StLIVE MUSIC VENUE in DOWNTOWN ANNAPOLIS.
Brick-walled tavern with a wisteria-covered heated patio serving pub fare & regional seafood dishes.
Local Theater! Wide variety of dramatic productions in the heart of downtown Annapolis. Standby tickets are usually available!
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The Colonial Players
108 East StLocal Theater! Wide variety of dramatic productions in the heart of downtown Annapolis. Standby tickets are usually available!
Shopping
Located in historic downtown Mills has a passion for fine wines, craft beers and a spirits selection like no one else & THEY DELIVER!
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Mills Fine Wine & Spirits
87 Main StLocated in historic downtown Mills has a passion for fine wines, craft beers and a spirits selection like no one else & THEY DELIVER!