Annapolis: More than the Academy

If you are looking for something a bit smaller and more colonial, the Historic Inns of Annapolis operates three charming inns in historic downtown — all within walking distance of Annapolis’ attractions. The most modern of the three dates back to 1776. All rooms are furnished in the colonial style and come with a private bath. Two of the inns are on State Circle with wonderful views of Maryland’s State House, and the other is at the top of Main Street with a great view of St. Anne’s Church on Church Circle. Seasonal rates begin at $189.

Where to eat — Annapolis has no shortage of good places to eat. Across the bridge from Annapolis (easy walk) is the Maritime Republic of Eastport — a tongue-in-cheek secession from the city — you will find some of the finest restaurants. For seafood, O’Learys Seafood Restaurant at 310 Third Street is the place to go. They have been a fixture of the Annapolis dining scene since 1984. The restaurant is known for its combination of award winning food, wine and service. Plus, it’s right on the water. O’Learys is only open for dinner and reservations are recommended. Call (410) 263-0884.

If you are looking to meet up with some locals, check out the Boatyard Bar & Grill at 400 Fourth Street. Here you will find the sailors and the waterman that make this town so unique. The dress is casual, and the food is simple but delicious. Order a beer, and try their jerk chicken skewers for an appetizer (order the beer first — you have been warned). Rumor has it that its crab cakes can’t be beat (I don’t do seafood; I know, wrong town). Dress is come-as-you are and it is very kid-friendly. The Boatyard also donates a portion of its profits to the Chesapeake Bay Foundation, so you can’t go wrong there. Drink up and Save the Bay! The number is (410) 216-6206.

For more typical bar food, try the Acme Bar and Grill (410-280-6486)at 163 Main Street. Anything Acme serves will be good but from a landlubber perspective, they have the best wings in town. With (at last count) 25 flavors, you need to try them all. My personal favorites are Island Zing, Chesapeake, Lemon Pepper, Honey Mustard, and Original. While there, take note of their collection of photos on the walls of the Acme-ites traveling all over the world. At night time, the younger crowd comes in and there is usually a live band to liven up the night. No reservations required.

The nightlife — It has been said that Annapolis is a drinking town with a sailing problem. But maybe it is the other way around. Or maybe it’s both. There is no shortage of nightlife in Annapolis — from hard rock, to punk, to soulful jazz, to a piano bar, to a national act. Walk up Main Street, Maryland Avenue, or Dock Street and you will find that most bars will have some sort of live entertainment virtually every night of the week.

The Rams Head Tavern hosts many national acts such as John Hiatt, NRBQ, The Capitol Steps, and Deanna Bogart. Tickets are available at the box office at 33 West Street or on their site. Buy early; this is a small venue and they sell out almost all the time. Call (410) 268-4545 for more information.

If you are looking for a smaller (some may say cramped) place, The Sly Fox Pub in the basement of Reynolds Tavern is a good bet. The pub is in the original tavern kitchen with the original foundation walls exposed and a large open fireplace. Happy Hours feature 20-ounce beers and specialty drinks. You can play darts all night and take in the sounds of local favorite Doug Segree. During the warmer months, the music moves outside to its terrace. Reynolds Tavern is open daily from 4:40 p.m. until midnight. The number is (443) 482-9000

If you are a smooth operator, no doubt jazz may be your thing. Located within the Loews Annapolis complex, the Power House has hosted some of the best live jazz. The jazz programming is done by Joe Byrd, brother of the legendary Charlie Byrd and their monthly Friday-Saturday shows are not to be missed. Housed in a centuries-old building with soaring ceilings and seating for only 110, you can experience jazz the way it was mean to be heard.

Some of the greats who have played here include the Joe Byrd Quintet, Brooks Tegler, and Tommy Newsome. Be sure to ask about the Jazz and Dinner package at the Loews. For upcoming acts, you can call (410) 269-0777 or visit its Web site.

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