Downtown Annapolis


The heart of Annapolis is full of a wide variety of museums, shops, pubs and eateries all within a short walk from our houses on Bay Ridge Ave.  The downtown area extends from the harbor, up Main Street, and then out across Church Circle to West Street.  The harbor, or Ego Alley as it is known to locals, is the span of water which stretches between Compromise and Dock Street connecting the Naval Academy and Spa Creek.  It has earned the moniker “Ego Alley” because of the many boat captains who dock their pride and joys along the bulkhead and bask in the attention of the many passersby. 

Making your way west from Ego Alley you’ll reach the foot of Main Street, one of the APA’s top 10 Great Streets in America for 2008.  Main Street is lined with 65 historic buildings that offer everything from sushi to sailing gear.  The brick lined streets and sidewalks rise up the hill to Church and State Circles where more boutiques, restaurants, and museums provide nearly everything our guests will need.  Those looking to bring a glimpse of Annapolis home with them should visit The Marion Warren Gallery on State Circle where one can browse Mr. Warren’s award winning photographs and gain an understanding of the history that shaped our unique town.  Whatever our guests desire, chances are it can be found in the heart of Annapolis, and all within a beautiful walk from our homes on Bay Ridge Ave. 

Bay Bridge

bridgeWhen the original span of the Bay Bridge was completed in 1952, it was the world’s longest over-water steel structure, stretching from Anne Arundel County, over the Chesapeake Bay and ending in Queen Anne’s County.  Since that time, another span has been constructed and together the bridges serve as the chief conduit between the Baltimore Washington Metropolitan area and some of the mid-Atlantic’s chief tourist destinations.  Situated less than 10 miles from the bridge, our homes on Bay Ridge Ave. provide guests with convenient access to Maryland’s Eastern Shore as well as the Delaware beaches, Ocean City, MD, Chincoteague, VA and Assateague Island.  With travel times to these destinations all around 2 hours, a day trip to the ocean becomes a very real mid-week possibility for our guests.  We would caution you against planning a trip to the beach during the weekend, however, as many of the metro area’s 8.5 million residences usually consider doing the same and traffic can be a nightmare. 



Founded in 1649, Annapolis has over 350 years of rich history that not only helped define the state of Maryland, but also the country itself.  Annapolis was named as Maryland’s capital in 1694 and actually served as the capital of the United States after the signing of the Treaty of Paris in 1783.  Through the city’s historical foundation, key historical sites and three centuries of architecture have been largely preserved for our guests to experience and enjoy today.  The Historic Annapolis Foundation , Discover Annapolis, and Watermark all offer a multitude of historical and scenic tours in and around Annapolis. 

Day Tripping

lighthouseThose not interested in the ocean, but looking to spend a day outside of Annapolis have a variety of different options.  Annapolis is conveniently located between its two larger siblings, Baltimore and Washington, DC, but it is also within close proximity to a number of lesser known, but equally appealing towns and cities.  On the Eastern Shore our guests can travel to St. Michaels, Easton, Oxford, and Chestertown, MD.  There are also options to the south with St. Mary’s City and Solomon’s Island and to the west in Frederick.  Each of these destinations offer a distinctive Maryland experience, and since they are all located within an hour or so of Bay Ridge Ave., they are extremely convenient for our guests to explore. 

Naval Academy

midsThe United States Naval Academy was established in 1845 and is today considered one of America’s preeminent institutions of higher learning.  The Brigade of Midshipmen has produced 73 Medal of Honor recipients, 50 astronauts, 45 Rhodes Scholars, 5 Chairmen of the Joint Chiefs, 3 Senators, 2 Nobel Prize Recipients, and in a manner of speaking a President.  However, according to some, the most prized alumni from Annapolis might be their only Heisman Trophy winner, Roger Staubach. 

At the beginning of July every year, the Academy’s first year Mids, also known as Plebes, come to Annapolis to begin their basic training or Plebe Summer.  During this time, the Plebes’ families usually accompany them to Annapolis and make a vacation out of their time spent here while their sons and daughters endure the crash course in naval procedures in the searing Annapolis summers.  Our houses on Bay Ridge Ave. provide the ideal setting for families looking to stay during part or all of Plebe Summer.  The many trips to Annapolis are just one of the benefits of your son or daughter receiving a free education from the Naval Academy. 

Throughout the year there are a whole host of activities to enjoy with respect to the Academy.  Many alumni choose to have their weddings in the Naval Academy Chapel cathedralwhich provides an opportunity for themselves and their classmates to return to Annapolis and enjoy the city they came to love.  A popular venue for rehearsal dinners and receptions is the Severn Inn, which sits directly across the river from the Naval Academy and provides a panoramic view of the entire campus. 

The Academy also has 29 Division I athletic teams which compete throughout the year.  While most of the games and matches are open to the public, the most popular events for fans to attend are the Navy Football games each fall.  Whether it’s the pregame flyovers, the cannon fodder after touchdowns, or the Plebes hammering out push-ups for every Navy point scored, a Saturday at the Navy-Marine Corps Stadium is unlike any other football game you’ll ever attend. 

After four years of study, a Midshipman is finally commissioned an officer with the rank of Ensign, which is the most junior level officer in the Navy.  The week leading up to this momentous occasion is known as Commissioning Week and it is by far the most exciting week in Annapolis all year.  Whether it’s watching the Mids attempt to scale a lard covered obelisk in the Herndon Climb, the Blue Angels air show, or the Presidential Address at the commencement ceremonies, there is always something exciting and uniquely Annapolis during Commissioning Week.   



As you may expect from a city located on the Chesapeake Bay, there is no shortage of great seafood restaurants in and around Annapolis.  Whether it’s fresh fish, shrimp, mussels, oysters, or the famous Chesapeake Blue Crab, our guests can enjoy some of the best seafood in the world without fear of repetition.  Really, the hardest choice you’ll have to make is what type of atmosphere you’re looking for.

Close & Casual

There are a number of great local places within the neighborhood of Eastport that our guests can easily walk to for a quick casual meal.  Davis’ Pub has been a local favorite since 1986 and is just a 5 minute walk from our homes on Bay Ridge Ave.  It offers indoor and outdoor seating and is the perfect place for a quick sandwich and a beer.  The Boatyard is another good little local restaurant located in Eastport, and its weekend brunch is perfect for our guests who are in town for a weekend and don’t feel like cooking breakfast. 

The Local Experience

Our guests hoping to try their hand at picking crabs really have only one destination to consider.  Jimmy Cantler’s Riverside Inn is without rival the area’s most famous crab house.  The staff there can give you a quick rundown on how to eat a crab, but once they’ve been dumped on the brown paper covered tables, it’s up to you to do it yourself.  We recommend that our guests wishing to go to Cantler’s call and get directions ahead of time.  As with many great local places, it’s a bit off the beaten path. 

The Best

Guests of ours desiring a true culinary experience should make the short drive across the Naval Academy Bridge to the Severn Inn.  Located on the opposite bank of the Severn River from the Academy, the Severn Inn provides its guests with an unparalleled view of Annapolis and a phenomenal dining event.  The Severn Inn is a Wine Spectator Award of Excellence winner and the winner of The Capital Readers’ Choice Awards for Best Place for a First Date and Best Outdoor Dining Experience.  The Severn Inn’s upper and lower decks are usually open from the beginning of May through the end of October and allow guests to experience 5 star dining in the open air and gentle breezes of the Severn River.  The menu features the very freshest seafood which arrives daily, choice cuts of beef and a fully stocked raw bar for the more adventurous patrons.  Reservations are strongly recommended. 



Every January, Maryland’s General Assembly convenes in Annapolis for 90 days to conduct the business of the state.  The 188 members of the Assembly are joined by their staff, lobbyists and citizens all looking to influence the outcomes of the more than 2300 bills acted on each session.  Our homes on Bay Ridge Ave. provide the perfect amount of space for senators, delegates, or lobbyists and their staffs looking to stay in Annapolis and be able to conduct business throughout the session.  Our homes are less than a mile from the State House and offer the requisite space needed for carrying out meetings that a hotel room simply cannot provide. 


sailA quick Google search of “America’s Sailing Capital” produces one name: Annapolis.  While the city is certainly deserving of this title, it does seem to discount powerboating as a viable means of recreation in the area.  Regardless of the semantics, Annapolis provides a world-class atmosphere for boating of all kinds, and proves this every October with the U.S. Sailboat Show and U.S. Powerboat Show held in Downtown Annapolis.  Our homes on Bay Ridge Ave. offer the ideal location for those wishing to either work at or attend the boat shows. 

But for guests staying with us throughout the warmer months of the year, there are a number of different options that allow you to experience the water even if you don’t have a boat.  Schooner Woodwind Cruises offers you the opportunity to help raise the sails, steer the boat, or just enjoy the ride.  Watermark is another popular charter service in the area that has a wide array of cruises for various prices and duration.  More exploratory guests can elect to captain a boat themselves and can either rent a powerboat from Annapolis Small Boat Rentals or a sailboat from Annapolis Bay Charters.  There are also kayak rentals available for visitors interested in exploring Ego Alley and Spa Creek through Annapolis Canoe and Kayak.  Whatever your desire may be, there are a plethora of different options available for our guests to discover Annapolis and the Chesapeake Bay by water.