Your Guidebook
Food scene
People drive an hour to experience the authentic Latin food and drink at Jesse Jays. They have seating both inside and out as well as take away. Grab a meal on your way in.
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JesseJay's Latin Inspired Kitchen
5471 Muddy Creek RdPeople drive an hour to experience the authentic Latin food and drink at Jesse Jays. They have seating both inside and out as well as take away. Grab a meal on your way in.
Ketch 22
7153 Lake Shore DrThe food is out of this world. The space is cool. The art is familiar.
If you want a splurge, Aqua Al 2 (said due) is the best restaurant in Annapolis. In fact, you would expect this caliber in NYC or LA. The atmosphere is classic set inside the second oldest building in Annapolis. The food is iconic Florentine and the cocktail menu is superb. They also have a bangin’ speakeasy in the basement. Plan ahead as they book up fast. Ciao!
Acqua al 2 - Annapolis
If you want a splurge, Aqua Al 2 (said due) is the best restaurant in Annapolis. In fact, you would expect this caliber in NYC or LA. The atmosphere is classic set inside the second oldest building in Annapolis. The food is iconic Florentine and the cocktail menu is superb. They also have a bangin’ speakeasy in the basement. Plan ahead as they book up fast. Ciao!
Pirate's Cove is consistent and delicious. Situated on Galesville Harbor, this place is the perfect choice to enjoy classic Chesapeake cooking either in the dining room, on the dock, or at one of their two bars.
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Pirates Cove Restaurant and Dock Bar
4817 Riverside DrPirate's Cove is consistent and delicious. Situated on Galesville Harbor, this place is the perfect choice to enjoy classic Chesapeake cooking either in the dining room, on the dock, or at one of their two bars.
Looking for some local food and culture, Dockside is a great choice. Really good food both inside and out. Local musicians and bands can be enjoyed nearly year round.
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Dockside Restaurant & Sports Bar
421 Deale RdLooking for some local food and culture, Dockside is a great choice. Really good food both inside and out. Local musicians and bands can be enjoyed nearly year round.
3 reasons you should go to Stan and Joes: Fresh Steamed Crabs, Legendary orange crushes, and an unforgettable view.
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Stan and Joes Riverside
4851 Riverside Dr3 reasons you should go to Stan and Joes: Fresh Steamed Crabs, Legendary orange crushes, and an unforgettable view.
If you want the region's best pie, an easy cup of coffee, or a fresh-baked scone, SCC is the place for you. Their sandwiches, soups, and breakfast are easily some of the best around.
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South County Cafe
5960 Deale Churchton RdIf you want the region's best pie, an easy cup of coffee, or a fresh-baked scone, SCC is the place for you. Their sandwiches, soups, and breakfast are easily some of the best around.
Sometimes I crave a bit of Irish. Killarney house has excellent traditional Irish food and their selection of authentic whiskey and beer is a nice treat too. Enjoy the roaring fire in the winter or the greenery around the patio in the summer. Year round, this place is a treat.
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Killarney House
584 W Central AveSometimes I crave a bit of Irish. Killarney house has excellent traditional Irish food and their selection of authentic whiskey and beer is a nice treat too. Enjoy the roaring fire in the winter or the greenery around the patio in the summer. Year round, this place is a treat.
Old Stein Inn
1143 Central Ave EMake sure you make a reservation. The Uber burger is the BEST!
A local favorite for years and years. Order your cream of crab soup ahead (sold on Fridays) as they sell out quickly. Great for breakfast and lunch and just a short bike or car ride away.
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Drift Wood Diner
1468 Snug Harbor RdA local favorite for years and years. Order your cream of crab soup ahead (sold on Fridays) as they sell out quickly. Great for breakfast and lunch and just a short bike or car ride away.
Alway's big sister is Annapolis Ice Cream Co. Some of the same flavors and all of the deliciousness. Just a 20-minute trip north and you'll be in ice cream heaven. And they have vegan options, too.
Always Ice Cream Company Edgewater
129A Mitchells Chance RoadAlway's big sister is Annapolis Ice Cream Co. Some of the same flavors and all of the deliciousness. Just a 20-minute trip north and you'll be in ice cream heaven. And they have vegan options, too.
Only open in the warm months, Ice cream lovers will travel 25 miles for a cone of this full-fat rich and delicious soft serve. You will need to travel just 2 miles.
Shadyside Soft Serve Ice Cream
6179 Shady Side RdOnly open in the warm months, Ice cream lovers will travel 25 miles for a cone of this full-fat rich and delicious soft serve. You will need to travel just 2 miles.
If you venture down to North Beach, you will not be disappointed when you enjoy the culinary treats offered at Hook & Vine. The cocktail program is innovative and the food is comforting and delicious.
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Hook & Vine - Kitchen and Bar
4114 7th StIf you venture down to North Beach, you will not be disappointed when you enjoy the culinary treats offered at Hook & Vine. The cocktail program is innovative and the food is comforting and delicious.
Great Mexican food with delicious margaritas. They have an excellent selection of agave spirits and an extensive menu that offers nearly every Mexican dish. I have been to this spot many, many times and always leave happy. Their outside seating area is generous and dog friendly!
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Plaza Mexico
9200 Bay AveGreat Mexican food with delicious margaritas. They have an excellent selection of agave spirits and an extensive menu that offers nearly every Mexican dish. I have been to this spot many, many times and always leave happy. Their outside seating area is generous and dog friendly!
This bakery os one of the best I’ve been to anywhere in the world. The bread is beautiful and delicious. They have yummy breakfast and lunch. Coffee is good to. Grab a loaf on your way in, it’s soooo worth the carbs. 👍
Black Market Bakers Edgewater
This bakery os one of the best I’ve been to anywhere in the world. The bread is beautiful and delicious. They have yummy breakfast and lunch. Coffee is good to. Grab a loaf on your way in, it’s soooo worth the carbs. 👍
Waterfront with beautiful food, delicious cocktails and really friendly staff. Make a reservation.
Baia Coastal Italian Kitchen & Wine Bar
Waterfront with beautiful food, delicious cocktails and really friendly staff. Make a reservation.
The cheese is obviously delicious, but the food and drinks are even better. Beautiful environment with one of the owners always in the building. You just can’t go wrong!
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Vaughan Cheese Counter & Bar
4116 7th StreetThe cheese is obviously delicious, but the food and drinks are even better. Beautiful environment with one of the owners always in the building. You just can’t go wrong!
Bars
A boat as a bar! Yep. This very energetic local spot is just a fun time. Lots of libations to keep you wanting more; all in a restored tobacco barn with a deadrise boat as your bar.
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The Boathouse
604 Cabana BlvdA boat as a bar! Yep. This very energetic local spot is just a fun time. Lots of libations to keep you wanting more; all in a restored tobacco barn with a deadrise boat as your bar.
Live music (Wednesday through Saturday), great drinks, good food and a view. What else do you need? Big Mary's is a slice of what makes South County what she is.
Big Mary's
4817 Riverside DriveLive music (Wednesday through Saturday), great drinks, good food and a view. What else do you need? Big Mary's is a slice of what makes South County what she is.
Nestled in the Capital Hotel in Annapolis, this place is the perfect spot for beautiful cocktails. Styled in a 20’s meets the 2020’s, the space is generous. The staff is knowledgeable and friendly. And of course, the cocktails are amazing. If your in town, treat yourself to The Parley Room, you won’t be disappointed. 🍸
Parley Room
Nestled in the Capital Hotel in Annapolis, this place is the perfect spot for beautiful cocktails. Styled in a 20’s meets the 2020’s, the space is generous. The staff is knowledgeable and friendly. And of course, the cocktails are amazing. If your in town, treat yourself to The Parley Room, you won’t be disappointed. 🍸
The bar at the end of the dock is a special place to hang. Beautiful views of Rockhold Creek and plenty of innovative twists on local recipes.
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Skipper's Pier Restaurant & Dock Bar
6158 Drum Point RdThe bar at the end of the dock is a special place to hang. Beautiful views of Rockhold Creek and plenty of innovative twists on local recipes.
This is an excellent local spot. The recently renovated space is a family owned and run bar with multiple places to relax. Enjoy live music on the weekends too.
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The Wheel House Beer Garden
4109 7th StThis is an excellent local spot. The recently renovated space is a family owned and run bar with multiple places to relax. Enjoy live music on the weekends too.
City
A local favorite and a destination for DC weekeders. Chesapeake Beach is filled with shops, restaurants, and bars. Enjoy a stroll on the boardwalk and have some ice cream or margarita.
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Chesapeake Beach
A local favorite and a destination for DC weekeders. Chesapeake Beach is filled with shops, restaurants, and bars. Enjoy a stroll on the boardwalk and have some ice cream or margarita.
Bars, eateries, and City Dock are all reasons that Annapolis should be on your shortlist of places to see. This iconic town is home to the Naval Academy, St. Johns College, and the State House. By day the town is teeming with tourists and families. By night, the bars are where the action is.
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Annapolis
Bars, eateries, and City Dock are all reasons that Annapolis should be on your shortlist of places to see. This iconic town is home to the Naval Academy, St. Johns College, and the State House. By day the town is teeming with tourists and families. By night, the bars are where the action is.
Close to Nature
You can walk, kyak or SUP your way to the beach just off the shore from the house. Gain a new perspective of where you are staying. Soak up some sun or get your heart pumping. This unique spot is everyone's favorite from the spring through the fall.
Idlewilde Restoration Project
Frederick AvenueYou can walk, kyak or SUP your way to the beach just off the shore from the house. Gain a new perspective of where you are staying. Soak up some sun or get your heart pumping. This unique spot is everyone's favorite from the spring through the fall.
If you want to enjoy the solitude of a costal forest, SERC is the place for you. With an array of planned events throughout the year, see what they may be up to while you are here.
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Smithsonian Environmental Research Center
647 Contees Wharf RoadIf you want to enjoy the solitude of a costal forest, SERC is the place for you. With an array of planned events throughout the year, see what they may be up to while you are here.
Jack Creek Park
1600 Snug Harbor Rd
Jug Bay Wetlands Sanctuary
1361 Wrighton RdSightseeing
Their annual Oyster Festival in October is the can’t miss event in Shady Side every year.
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Captain Salem Avery Museum
1418 E West Shady Side RdTheir annual Oyster Festival in October is the can’t miss event in Shady Side every year.
Essentials
Easy in and easy out grocery store, selling all of the essentials. Boar’s Head deli, fantastic bagels and prepared foods.
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Christopher's Fine Foods
5570 Shady Side RdEasy in and easy out grocery store, selling all of the essentials. Boar’s Head deli, fantastic bagels and prepared foods.
They probably have what you need. On the way from DC, the very friendly staff with help you when you need them.
Captain Kidds Liquors
5823 Deale Churchton RdThey probably have what you need. On the way from DC, the very friendly staff with help you when you need them.
This place has a massive beer and wine section with a highly knowledgeable staff. All the sprits you can ask for in a well laid out store. Safeway is right next door.
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Edgewater Liquors
54 W Central AveThis place has a massive beer and wine section with a highly knowledgeable staff. All the sprits you can ask for in a well laid out store. Safeway is right next door.
Activities
Honey's Harvest Farm
5801 Brooks Woods RdFUNtastic and relaxing SAILING trips from historic Annapolis about 30 minutes away. Join Captain Paul Foer on his restored classic sailboat 38' sailboat, "Non Sea Quitter", as we sail on the Severn River and Chesapeake Bay where he grew up boating with his family.
Non Sea-Quitter LLC
921 Boucher AveFUNtastic and relaxing SAILING trips from historic Annapolis about 30 minutes away. Join Captain Paul Foer on his restored classic sailboat 38' sailboat, "Non Sea Quitter", as we sail on the Severn River and Chesapeake Bay where he grew up boating with his family.
A great way to learn how to SUP, rent or enjoy some SUP yoga.
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Chesapeake Paddle Sports
6124 Drum Point RdA great way to learn how to SUP, rent or enjoy some SUP yoga.
Fishing the Chesapeake Bay with Licensed Charter & Fishing Guide. Last Hurrah Charter Fishing strives to provide one the best charter fishing operations on the Chesapeake Bay. They offer a full service, first class fishing experience which is customized to accommodate everyone from beginner to the most advanced angler.
Last Hurrah Fishing Charters
487 Deale RdFishing the Chesapeake Bay with Licensed Charter & Fishing Guide. Last Hurrah Charter Fishing strives to provide one the best charter fishing operations on the Chesapeake Bay. They offer a full service, first class fishing experience which is customized to accommodate everyone from beginner to the most advanced angler.
A journey to wine country without leaving town. The rural country setting is magical. You drive through a working cattle farm before you arrive at the vineyard. It creates the illusion of stepping through a suburban portal and arriving at a rural destination that could be a thousand miles away. The grounds are immaculate, the tasting room intimate and the owners, Doug and Maureen are always gracious
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Thanksgiving Farm Winery
195 Harwood RdA journey to wine country without leaving town. The rural country setting is magical. You drive through a working cattle farm before you arrive at the vineyard. It creates the illusion of stepping through a suburban portal and arriving at a rural destination that could be a thousand miles away. The grounds are immaculate, the tasting room intimate and the owners, Doug and Maureen are always gracious
A real treat not too far away. The vineyard offers a beautiful setting among the rolling countryside of Davidsonville. The wine is pleasant and the farm is special.
The Vineyards at Dodon
391 Dodon RdA real treat not too far away. The vineyard offers a beautiful setting among the rolling countryside of Davidsonville. The wine is pleasant and the farm is special.