Travel Packages at Flag House Inn

Naval Academy visits, Blue and Gold training, sailing schools, sporting events or history, business and retirement travel: whatever brings you to Annapolis, the Flag House Inn is your best base of operations with free off-street parking and great accommodations.   

Contact us about special pricing, best days/time of year for discounts and other interests so we can assemble a package to maximize your experience.

Details of Specials: 

Blue & Gold Officers & Naval Academy Visits
Sailing Schools
St. John’s College
Retirement Travel
Historic District Tourism
Business Meetings and Executive Retreats
Legislative Session

Blue & Gold Officers & Naval Academy Visits 
The Flag House Inn extends a special invitation to Blue & Gold officers.  

Flag House has THE best location for visiting the USNA and in-town:

  • Located directly across from main gate to Naval Academy
  • On-site parking at no extra cost.
  • King-size beds for extra comfort.
  • In-room full bathrooms, wi-fi, air conditioning and cable TV
  • Large assortment of Academy related reading materials.
  • Naval art and antiques and Academy memorabilia

Sailing Schools & Boat Shows

  • Spring Boat Show
  • Fall Boat Shows
  • J-World
  • Annapolis Sailing School
  • Chesapeake Sailing School

At Flag House Inn, Enjoy the Best of Both Worlds:

  • Centrally located for the sailor – walk to your location while enjoying off-street parking 
  • Relax in the heart of Annapolis’ nightlife.
  • Enjoy Flag House’s sailing and maritime heritage.
  • The best pubs and restaurants in town
  • The U.S. Naval Academy Sailing Center & Museum & US Naval Academy model ship gallery: one of the finest in the world.
  • City Dock: Annapolis’ maritime center since 1696.
  • The Annapolis Maritime Art Gallery for fine paintings & prints.

At Flag House Inn you enjoy on-site parking at no extra cost, delicious breakfast to start your day, King-size beds for extra comfort, and in-room full bathrooms, wi-fi, air conditioning and cable TV.

Discounts offered for sailing school extended stays (4 or more days not including weekend days or major event weeks).

St. John’s College
Flag House Inn is located three blocks from the College campus. We welcome alumni, parents and friends of current students.

Admissions Visits: We can identify any off peak pricing or timings to plan your trip. If party of 3, we have a suite so the family can stay together 

Retirement Travel
Flag House Inn is noted for comfort, security & convenience.  We are the Ideal place for the quality conscious traveler while still offering great value:

  • Priced competitively with other Historic District inns and hotels of similar quality.
  • Free parking on site: compare with  hotel parking and limited on-street parking (2 hour maximum).
  • Full breakfast with all the trimmings and a K Cup machine for coffee & tea on the go
  • Insider’s advice on the best deals in town for lunch, dinner, boat excursions, tours, and so much more.

Plus: The peace & privacy advantages of a private historic home and personally owned and operated by your hosts

Retiree Advantages: We’re close (within 4 blocks!) to everything.
Ease of coming & going: a great advantage in rainy, hot or cold weather, or during a busy day. 

Historic District Tourism

The Flag House Inn Advantage:

  • An authentic & historic bed & breakfast inn, not a hotel, located in the colonial waterfront sector of Annapolis
  • Historic Victorian in the National Historic District.
  • On-site parking at no extra cost.
  • Members of the Historic Annapolis Foundation & National Trust for Historic Preservation..
  • Closest to the U.S. Naval Academy

Within 3 Blocks: The Heart of the Colonial Area:

5 of the finest Georgian colonial mansions in America:
William Paca House & Gardens (1763), museum
Hammond-Harwood House (1774), museum
Chase-Lloyd House (1769), open to the public
McDowell Hall (1744), St. John’s College Campus
James Brice House (1767)
25 significant colonial buildings dating to 1680.
Maryland State House (1772), tours open to the public.
Scores of other colonial, federal, and Victorian buildings.

Helpfulness at Flag House Inn: Find the ideal walking, bus or boat tour.
Latest Annapolis historic guidebooks and pamphlets.
Insider’s recommendations on area day trips.

Business Meetings and Executive Retreats

Meeting space available with full house rental. 
Cooperative room placement with neighboring B&B’s and other accomodation
Competitive pricing. Coming from the corporate world with extensive experience in training & events, Marty can work with you to tailor our support to your unique needs.

Team Up with the Schooner Woodwind: This two-masted purpose-built schooner, sailing from City Dock, specializes in corporate charters and exciting team-building sailing exercises—a perfect way to begin or end your retreat at Flag House!

Legislative Session
If you are involved in the Maryland Legislative session running January to mid-April, we can develop a tailored package for your needs, whether it is a block booking or an a la carte package.

No matter if you are a legislator, staffer, lobbyist or consultant, you’ll find the Flag House Inn is a quiet and secluded base for your busy time in Annapolis. We’ll provide breakfast and can work with you on any other needs you may have, including meetings and events.