By May 27, 2005 Read More →

Annapolis: More Than The Academy

The Blue Angels have just completed their last flyover. The presidential motorcade is heading back to a waiting Marine One, and all of the Midshipman have picked up their hats. Now that all the hustle and bustle of Commissioning Week — better known to us civilians as graduation — is over, Annapolis, Md., will calm down. The locals will have their town and harbor back for a little while until the summer tourists begin their annual migration.

Whether you come for the history, the education, the water, or the hospitality, there is always something to enjoy in Annapolis. The city has been welcoming visitors for more than 300 years.

While Annapolis may seem synonymous with the United States Naval Academy, this world-famous institution isn’t even the oldest college in town. That distinction belongs to St. John’s College, founded in 1696 as King William’s School. It is the third oldest college in the United States, after Harvard and William and Mary. But our city offers so much more.

The capital of Maryland was the capital of the United States when the Treaty of Paris, ending the Revolutionary War, was signed here. All four Maryland signers of the Declaration of Independence had impressive homes — all still standing — in Annapolis.

Any sailor worth his salt knows Annapolis. Its harbor plays home (temporarily) to boats from all over the world during one of the largest in-water boat shows in the world in October. (That event is a love/hate thing with the locals). And beneath those waters lie the hulls of the Peggy Stewart, burned during a tax revolt, and the great yacht “America” of America’s Cup fame. Annapolis Harbor is the same harbor where Kunte Kinte was sold into slavery and its working-class dock is where PT boats and mine sweepers for two world wars were built.

But if you are not a world-class sailor, what is there to do in Annapolis? That’s an easy answer. The tough one is: how to do it all?

Where to stay — Annapolis (at the moment) has an admitted shortage of hotel rooms so making a reservation as far in advance as possible is strongly recommended. The Loews Annapolis Hotel balances elegance and charm in a location that’s unrivaled. It is the city’s most luxurious hotel, with premier services, amenities, and meeting facilities. Located on West Street, within walking distance of pretty much everything, the Loews puts you in the middle of it all. The hotel has 217 rooms, one fabulous restaurant called Breeze, a great little bar called the Weather Rail, and a Jazz Club called the Power House. Rates at the Loews begin at $189 per night.

If are looking for that waterfront experience, the Annapolis Marriott Waterfront is the only place to go. Renovated in April 2005 (thanks to the 8 feet of water in the lobby from Tropical Storm Isabel), this hotel offers 150 deluxe rooms right on Annapolis Harbor. If you have ever been to Soper’s Hole in Tortola, you know Pusser’s Landing—well. They’ve got one, too. Sip a drink on the deck overlooking “Ego Alley” — where all the boaters come to show off their latest floating toys (and the locals tend to snicker at their pretentiousness), or look out across the harbor to see the mega-yachts with foreign home ports.

During the past year, Eric Clapton, Steve Forbes, and Walter Cronkite, have all moored their yachts in our harbor calling Annapolis home, at least for a while. Rates at the Marriott run $275 and up per night.

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 itsr Web site.

And now for the “touristy” stuff — Annapolis needs to be experienced by both land and water. Annapolis Tours offers several walking tours of this scenic town. Your colonial-attired guide is the ideal way to delve into historic Annapolis and the rich tradition of the US Naval Academy, the State House (the oldest state house in the US in continuous use and the largest wooden dome in the country).

Annapolis Tours will take you on a tour of the private home of a signer of the Declaration of Independence and will offer a bird’s eye view of nearly 4,000 midshipmen in formation at the Naval Academy. Other tours include a Candlelight Stroll, Scavenger Hunt, African-American Heritage tour, Military Reunion tours, and a Haunted History tour. These are all appropriate for all ages and are very entertaining. (Even as a local, I have been on several and learn something new each time.) Annapolis Tours can be reached at (410) 268-7601.

Of course, you can’t visit Annapolis without seeing water. Watermark Cruises operates most of the public water transportation in town, including the water taxi service available at the City Dock and other points along Spa and Back Creeks. While they offer shorter excursions from the City Dock, one of the most encompassing voyages is the 2 ½-hour Bay Lighthouses Tour. You will be hosted on the brand new 65-foot motor-yacht, Lady Sarah, which will take you out of the harbor, under the twin spans of the Bay Bridge. Your “lighthouse keeper” (guide) will provide an entertaining history of our three prominent lighthouses — Sandy Point, Thomas Point, and Baltimore Harbor.

If you don’t have that much time, try the Miss Elizabeth, which will take you around the seawall of the Naval Academy and up Spa Creek to view some of the fabulous waterfront homes — she runs from City Dock. Reservations are not required but can’t hurt. Contact Watermark Cruises at their website or at 410-268-7601.

Still need more scoop? Check out the following resources for planning your visit to Annapolis, and if you are planning on coming, drop me an email and I might let you in on some more insider scoop. After all, we locals need to keep some things to ourselves.

Additional resources:

City of Annapolis (
The Maritime Republic of Eastport (
Annapolis and Anne Arundel County CVB (
Annapolis and Anne Arundel County Chamber of Commerce (
United States Naval Academy (
St. John’s College (
Watermark Cruises (
Annapolis Tours (

Posted in: Our Articles

About the Author:

Comments are closed.

%d bloggers like this: