Ian's Guidebook
Food Scene
This is arguably my favorite restaurant in Annapolis. Huge menu, great food, reasonable pricing, fun atmosphere.
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Boatyard Bar & Grill
400 Fourth StThis is arguably my favorite restaurant in Annapolis. Huge menu, great food, reasonable pricing, fun atmosphere.
This place is a unique gem. Absolutely amazing food, reasonably priced to boot. They do not accept reservations and it's a popular spot on the weekends, so be prepared for an hour plus wait (you can, of course, start sampling their large wine selection while you wait).
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Vin 909 Winecafe
909 Bay Ridge AveThis place is a unique gem. Absolutely amazing food, reasonably priced to boot. They do not accept reservations and it's a popular spot on the weekends, so be prepared for an hour plus wait (you can, of course, start sampling their large wine selection while you wait).
This is a blast from the past, 50's diner style. Good cheap food, with an anesthetic right out of the 50's. You may feel like a sardine. Massive menu and big portions, this "delly" has been featured on Man vs Food and various other foodie-type TV shows.
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Chick & Ruth's Delly
165 Main StThis is a blast from the past, 50's diner style. Good cheap food, with an anesthetic right out of the 50's. You may feel like a sardine. Massive menu and big portions, this "delly" has been featured on Man vs Food and various other foodie-type TV shows.
If you want a fancy dinner, this is the place. The dining room overlooks Annapolis harbor with tall glass windows. The happy hour is killer.
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Chart House
300 Second StIf you want a fancy dinner, this is the place. The dining room overlooks Annapolis harbor with tall glass windows. The happy hour is killer.
I've been to many an "Irish pub" where the only thing Irish about the place was the name... Not so here. Owned and staffed by irishmen & women, with a more authentic menu than half the Irish pubs I've been to in Dublin (they occasionally even have haggis on the menu!) and a wonderful whiskey selection. Go on a Wednesday night to experience a traditional Irish "Seśiun" and hear a half dozen musicians play traditional Irish tunes.
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Galway Bay Irish Restaurant and Pub
63 Maryland AveI've been to many an "Irish pub" where the only thing Irish about the place was the name... Not so here. Owned and staffed by irishmen & women, with a more authentic menu than half the Irish pubs I've been to in Dublin (they occasionally even have haggis on the menu!) and a wonderful whiskey selection. Go on a Wednesday night to experience a traditional Irish "Seśiun" and hear a half dozen musicians play traditional Irish tunes.
In competition with the Boatyard for my favorite restaurant in Annapolis. Great Mexican food, owned by a Mexican family (if you see an older gentleman with a mustache right out of a movie walking around, that's the owner). You'll see soccer on the TV's, and if it's a weekend you'll more than likely see some kind of large, entertaining-to-watch group from a wedding party, Batchelorette party, birthday, or some other event.
El Toro Bravo
2552 West StIn competition with the Boatyard for my favorite restaurant in Annapolis. Great Mexican food, owned by a Mexican family (if you see an older gentleman with a mustache right out of a movie walking around, that's the owner). You'll see soccer on the TV's, and if it's a weekend you'll more than likely see some kind of large, entertaining-to-watch group from a wedding party, Batchelorette party, birthday, or some other event.
The food isn't good, and the drinks aren't the cheapest. Two things redeem this bar: one, the dock bar. Drink or dine right on the edge of the Chesapeake. Great place to watch the sunset (and people cruising by showing off their expensive powerboats).
And two: the people watching. Especially after 10pm. If you're lucky, you may see someone stumble right off the dock into the bay!
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Pusser's Caribbean Grille
80 Compromise StreetThe food isn't good, and the drinks aren't the cheapest. Two things redeem this bar: one, the dock bar. Drink or dine right on the edge of the Chesapeake. Great place to watch the sunset (and people cruising by showing off their expensive powerboats).
And two: the people watching. Especially after 10pm. If you're lucky, you may see someone stumble right off the dock into the bay!
Food Scene
This is Eastport's "locals only" dive bar. Pub food, cheap drinks, sports games and a few inebriated locals. Off the beaten path and away from the touristiness of downtown.
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Davis's Pub
400 Chester AveThis is Eastport's "locals only" dive bar. Pub food, cheap drinks, sports games and a few inebriated locals. Off the beaten path and away from the touristiness of downtown.
Sightseeing
Great music venu with a wide range of artists. Same day tickets usually available.
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Rams Head On Stage
33 West StGreat music venu with a wide range of artists. Same day tickets usually available.
Sightseeing
There are several "cruise tours" of Annapolis harbor and the Chesapeake Bay, and in my humble opinion this one is the best. You'll ride along on a schooner designed specifically for the Bay's moderate winds and flat water, and you'll get some real time on the water (~2 hrs per tour) vs the ~20-30 minute spin around the bay that many other tours offer. If you can get a ticket for the sunset cruise, that's an especially magical ride!
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Schooner Woodwind Sailing Cruises
80 Compromise StThere are several "cruise tours" of Annapolis harbor and the Chesapeake Bay, and in my humble opinion this one is the best. You'll ride along on a schooner designed specifically for the Bay's moderate winds and flat water, and you'll get some real time on the water (~2 hrs per tour) vs the ~20-30 minute spin around the bay that many other tours offer. If you can get a ticket for the sunset cruise, that's an especially magical ride!