Guidebook for Annapolis
Food Scene
Only open for Breakfast and lunch. Great value for the quality. This is the locals spot. I eat here at least twice a week.
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Eastport Kitchen
923 Chesapeake AveOnly open for Breakfast and lunch. Great value for the quality. This is the locals spot. I eat here at least twice a week.
This place is very Annapolis in a very local way. One of the best sailors hangouts anywhere. They will have video from local around the buoy racing on the TVs following regattas. If you look hard enough you will find my name on a couple trophies in there.
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Boatyard Bar & Grill
400 Fourth StThis place is very Annapolis in a very local way. One of the best sailors hangouts anywhere. They will have video from local around the buoy racing on the TVs following regattas. If you look hard enough you will find my name on a couple trophies in there.
Simply incredible! Amazing creative local farm to table dishes! No reservations. The wait is not only worth it but a lot of fun. Most nights the lounge is crowded with other like minded foodies enjoying a drink waiting for their table. A very Eastport experience.
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Vin 909 Winecafe
909 Bay Ridge AveSimply incredible! Amazing creative local farm to table dishes! No reservations. The wait is not only worth it but a lot of fun. Most nights the lounge is crowded with other like minded foodies enjoying a drink waiting for their table. A very Eastport experience.
If you want a Steak... I am not saying Ruth's Chris isn't great. I am saying Lewnes' is a little better. This is a full service fine dining restaurant. When my wife and I want to go out this is our go to. Definitely make reservations.
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Lewnes' Steakhouse
401 Fourth StIf you want a Steak... I am not saying Ruth's Chris isn't great. I am saying Lewnes' is a little better. This is a full service fine dining restaurant. When my wife and I want to go out this is our go to. Definitely make reservations.
Guy Fieri stopped here when he was doing his Diners, Drive-Ins and Dives. This place is local Eastport comfort food at its finest. If you are in town Monday-Wednesday stop in for lunch and enjoy homemade pot roast, meatloaf, or thanksgiving dinner for less then $10. There are covered outdoor picnic tables with full service overlooking Back Creek.
This is also a great place to have some drinks with the locals late into the evening. Friendly, always entertaining bunch. Great for when you are tired of Downtown and you just want to relax.
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Davis's Pub
400 Chester AveGuy Fieri stopped here when he was doing his Diners, Drive-Ins and Dives. This place is local Eastport comfort food at its finest. If you are in town Monday-Wednesday stop in for lunch and enjoy homemade pot roast, meatloaf, or thanksgiving dinner for less then $10. There are covered outdoor picnic tables with full service overlooking Back Creek.
This is also a great place to have some drinks with the locals late into the evening. Friendly, always entertaining bunch. Great for when you are tired of Downtown and you just want to relax.
Great spot to watch boats headed into Annapolis Harbor and see the sailboats finishing Wednesday night races. In the Winter there is frostbite racing to watch on Sunday afternoon. Excellent menu. Make sure you order the Lava Cake at the beginning of the meal! This is also a water taxi stop. The boat will take right into downtown.
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Chart House
300 Second StGreat spot to watch boats headed into Annapolis Harbor and see the sailboats finishing Wednesday night races. In the Winter there is frostbite racing to watch on Sunday afternoon. Excellent menu. Make sure you order the Lava Cake at the beginning of the meal! This is also a water taxi stop. The boat will take right into downtown.
Entertainment & Activities
Just a .4 mile walk. SUP, Kayak, and Peddalboard rentals. Enjoy Annapolis from Spa Creek and get a great workout. Hourly rates and friendly staff. Check for availability.
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Capital SUP
655 Edgewood RdJust a .4 mile walk. SUP, Kayak, and Peddalboard rentals. Enjoy Annapolis from Spa Creek and get a great workout. Hourly rates and friendly staff. Check for availability.
Just a .6 mile walk. Kayak, Canoe and SUP rentals. Enjoy Annapolis from Spa Creek and get a great workout. Hourly rates and friendly staff. This place is cool. Lots of water toys to play with. Check for availability.
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Annapolis Canoe and Kayak, LLC
311 Third StJust a .6 mile walk. Kayak, Canoe and SUP rentals. Enjoy Annapolis from Spa Creek and get a great workout. Hourly rates and friendly staff. This place is cool. Lots of water toys to play with. Check for availability.
Mission Escape Rooms
40 West StGreat family fun with a number of skill levels.
Just an 8 min UBER ride with normal traffic. 2.4 miles away.
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Stadio commemorativo della Marina e del Corpo dei Marines della Marina degli Stati Uniti
550 Taylor AveJust an 8 min UBER ride with normal traffic. 2.4 miles away.
Essentials
Rite Aid
1815 Connecticut Ave NWFull service pharmacy directly across the street.
Parks & Nature
Just 2.3 miles away. This is an incredible park with hiking/bike trails, kayak and SUP rentals as well as a summer concerts and events. Typically not very crowded. Definitely a locals spot to enjoy the woods and water.
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Parco delle Acque Tranquille
600 Quiet Waters Park RdJust 2.3 miles away. This is an incredible park with hiking/bike trails, kayak and SUP rentals as well as a summer concerts and events. Typically not very crowded. Definitely a locals spot to enjoy the woods and water.
Sightseeing
Watermark tours has both boat and walking tours in Annapolis. The Harbor Queen will get you out on the water for a quick tour of Annapolis harbor and Naval Academy. You can also get the flavor of Annapolis by taking one of their many water taxis. If you want to save your feet, and have a fun boat ride, you can pick up water taxis at Davis Pub and The Chart House in Eastport. They will drop you off right downtown. Watch the weather!
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Watermark Tours, Charters, Cruises
1 Dock StWatermark tours has both boat and walking tours in Annapolis. The Harbor Queen will get you out on the water for a quick tour of Annapolis harbor and Naval Academy. You can also get the flavor of Annapolis by taking one of their many water taxis. If you want to save your feet, and have a fun boat ride, you can pick up water taxis at Davis Pub and The Chart House in Eastport. They will drop you off right downtown. Watch the weather!
More of a hands on boating experience in Annapolis. Some of the summer sunset cruises can get a little crowded. The best nights to go out are Wednesdays and Thursdays March-August. These are the local sailboat racing nights. Ask before you book.
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Schooner Woodwind Sailing Cruises
80 Compromise StMore of a hands on boating experience in Annapolis. Some of the summer sunset cruises can get a little crowded. The best nights to go out are Wednesdays and Thursdays March-August. These are the local sailboat racing nights. Ask before you book.
Just 1.2 miles and a beautiful historic and scenic 23 min walk. Safe sidewalks all the way. You are welcome to walk(not drive) onto the Academy Grounds with a passport or State issued ID. Always check security notices before planning your trip.
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Naval Academy
Just 1.2 miles and a beautiful historic and scenic 23 min walk. Safe sidewalks all the way. You are welcome to walk(not drive) onto the Academy Grounds with a passport or State issued ID. Always check security notices before planning your trip.
Arts & Culture
Very Small. Great information about Chesapeake Bay Ecology and specifically Oysters. Its Free. If you are having a drink or lunch at Davis' Pub this is worth a quick look.
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Annapolis Maritime Museum & Park
723 Second StVery Small. Great information about Chesapeake Bay Ecology and specifically Oysters. Its Free. If you are having a drink or lunch at Davis' Pub this is worth a quick look.