Things to Do on Vacation in Annapolis, MD

The campus of USNA is compact, very walking friendly and very scenic as you can look out into Annapolis Harbor and the Severn River/ Chesapeake Bay from the grounds. The most popular attractions include:

• Visitor Center – take the 90-minute guided walking tour and shop the tax-free gift shop
• Bancroft Hall – Where all midshipmen live – there is a magnificent public area
• USNA Chapel – awe inspiring. Sometimes closed for events/weddings. Can also visit crypt of John Paul Jones underneath (naval hero)
• Preble Hall Museum – little-known gem featuring history of US Navy with amazing artifacts. MUST visit 2nd floor for ship models display
• Lunch formation – in season, see the entire Brigade (the whole school!) line up at noon. Only takes 10 minutes.
• Also…. Mon-Fri, the officers club is open for lunch and also walkable is John McCain’s gravesite, we can guide you. In season, see the Friday afternoon parades and other special events.

We recommend taking the walking tour right after breakfast. Allow 2-3 hours to visit though many guests spend the whole day on site!

We can further guide you with maps, info on special events and help you with any other questions or needs.

Special Academy Events

Flag House Inn is convenient for:

• Commissioning Week
• Induction Day
• Parents’ weekends
• Alumni reunions
• Football weekends
• Weddings
• Drop off and pick up from summer camps, sports tournaments and other special US Naval Academy activities

The Woodwind offers numerous options, whether it’s a 2-hour daytime sail, a sunset cruise or even a charter for your group.  If the wind is up, it’s absolutely the best activity going! And even without much wind, the crew will take you out from Annapolis Harbor out on the Bay. And best of all, you can walk to the dock from Flag House Inn!

For a more intimate experience on the water, rent a kayak or stand-up paddleboard.  This includes options such as Annapolis Canoe & Kayak (Eastport – walk), Quiet Waters Park (15 min, see our blog), Kayak Annapolis (Spa Creek, 10-min drive)

There are many other boat charters available, including:

• Annapolis Electric Boat Rentals – Eastport – great for private outing for 2-12 people.  Self driven boats for 1-4 hour tour of Spa Creek, Back Creek and around the harbor.
• Island Chill Yacht Charters – both power and sail boats. (20-min drive)
• Classic Sail Charters – Guests have used this service and raved about them
• There are many outings with Watermark, see the separate posting

Here’s our custom walking tour recommendation:

1. Turn right out of the FHI, take first right at light and walk up Prince George St, admiring the colonial style homes built from late 1700’s to early 1900’s. Optional: William Paca House & Gardens
2. At Maryland Ave, turn right, stop into Old Fox bookstore / Brown Mustache coffee. Browse a bit or have a coffee.  Turn left and head back to Prince George St. when you leave…
3. Turn right on Prince George, take to the end, cross over to St John’s College – established 1696. Very unique curriculum. Have a rest on the grounds. Go back down Prince George to Maryland Ave, turn right.
4. Browse the shops on Maryland Ave., stop into Galway Bay Irish pub for a beverage or snack. Continue on Maryland to State Circle.
5. Turn left and loop around State Circle, can stop into Maryland State House, sit awhile on the grounds. Pass the Governor’s mansion. At Church Circle, take a left, walk around to Main St (optional – continue around Church Circle to West St., the visitor center is located here as well as many shops and eating/drinking. Can also cross Church Circle to St Anne’s church. Observe the ancient gravestones)
6. Walk down Main St, stopping into as many shops, bars, restaurants, and ice cream stores as you can handle! When you get to the traffic circle near the harbor, you can either turn left and walk two blocks back to Flag House Inn for a rest or continue through the circle and walk over to Eastport.
7. On the way back (or at beginning of tour) walk out on City Dock to the lookout over the harbor… walk past Ego Alley…. Very scenic and great spot for sunrise or sunset.

While this doesn’t cover every attraction in town, this will give you a good feel for the town.  We have the comprehensive visitor’s guide on hand.  

The historic homes in Annapolis include:

• William Paca House and Gardens (1763) – huge home, the “townhouse” of Declaration of Independence signer.  Lovely 2 acre gardens
• James Brice House (1767) – take the hardhat tour when available.
• Hammond-Harwood House (1774) – renowned architecture, curated with many original objects from Colonial times
• Chase Lloyd House (1769) – site of wedding of Francis Scott Key (Star Spangled Banner author). Built by signer of Declaration of Independence
• Banneker – Douglass Museum (1790) – Maryland’s museum of African-American history from 1633 to today.  Daily.
• Charles Carroll house (1720’s) – birthplace of Declaration of Independence signer, family dates to original settlers in Maryland in late 1600’s.  Adjacent to St Mary’s church (1860)
• Hogshead – Rare surviving example of a building type that was common in 18^th-century Annapolis.  See how working class lived. Open on weekends.
• Alex Haley/Kunta Kinte memorial – site of 1767 arrival of slave as immortalized in “Roots”
• Annapolis Maritime Museum – Pair with lunch at Davis’ Pub or other Eastport locations

There are even more historic homes in and around Annapolis.  If history is your thing, you need to come to Annapolis!

Further historical background

The city was established in 1649 and was first known as Anne Arundel Town after Lord Baltimore’s wife.  The name was changed in honor of Princess Anne of England when the capital of Maryland was moved from St. Mary’s City to Annapolis.  The city charter was given in 1708.

From 1783 – August 1784 it was the United States’ first peacetime capital.  George Washington resigned his commission as General of the Continental Armies in the Maryland State House in 1783. The Treaty of Paris, which ended the American revolutionary war, was ratified here in 1784.

In 1808 Fort Severn was built in Annapolis and helped to prevent British attacks on the city during the War of 1812. The fort was inhabited by soldiers until 1845, and in 1850 it was transferred to the US Navy and became the US Naval Academy.

Well into the nineteenth century the area remained agrarian, but as growth in the twentieth century in the Baltimore and Washington DC areas came, so did growth in Annapolis. Annapolis did not grow as fast as Baltimore’s harbor is much larger and Washington became the Federal capital, but Annapolis has held its own unique position as both State capital, home of the Naval Academy and a sailing center for the Chesapeake Bay.

Today there are more original 18^th-century homes in existence and in use here than in any other city in the US.

Our guests and ourselves have experienced many of these specialty tours, they cover a range of topics.  Be sure to call ahead for all of these as the schedule changes based on day of week and time of year:

• Naval Academy walking tour – offered by USNA – see details in USNA section.  Get great insight and stories on the history of the USNA in Annapolis
• Watermark – 4 Century walking tour, Ghost tour, Architecture tour – wide variety of tours.  We have current weekly schedule available in sitting room
• Tours & Crawls – wide variety, fun guides: Ghost tour, Pub Crawl, Twisted history
• Colonial Tours of Annapolis – costumed guides lead 2 hour walking tours. Sun-Thu from May-Oct. Departs visitor center
• Trolley tour – let the drivers take you around! Check the schedule, operates seasonally. Departs from visitor center
• Urban EvenTours – small group tour in small electric cart – Food tours, city tours, custom tours. Call ahead
• Haunted Harbor tours – Factual ghost tour. Leaves from city dock

We’ll add more as we find out.  We have gone on several of these tours and can offer our insights.

Construction started in 1772, and the building was gradually expanded into what you see today.  The State House is open every day 9a – 5p except Christmas and New Year’s Day.  There is a great view and spacious grounds around the State House. The Governor’s mansion is adjacent to the State House.

There are numerous high-quality restaurants nearby to Flag House Inn in downtown Annapolis also, and we have sampled most every one and can offer our recommendations. We have our favorites, but more importantly we listen to what our guests are saying too. 

See our blog where we discuss all the choices in more depth.

Here are some of our favorite options for a short outing:

• Quiet Waters Park – lovely park with hiking, biking, picnicking and canoe/kayak rentals. (see our blog)
• Historic London Town & Gardens.  Lovely setting on the South River only about 20 minutes away. Check ahead for re-enactments.  Take a walk through the wooded gardens Have lunch / drinks at several nearby riverfront pubs.
• Baltimore & Annapolis trail – starts 3 miles from FHI, great for biking, also hiking. Leave from the Inn or drive to parking area.  13 miles to BWI airport, can then do 8 mile loop around airport and back…. Very few road crossings.
• Great Frogs Winery – recently opened, features nice setting within several tasting rooms. Pair with a trip to Thomas Point park for nice lookout to the Bay. Book ahead for tasting.
• Cantler’s – the Chesapeake steamed crabs experience. Always named a top crab house in Maryland. Their crab soup and soft shell sliders are pretty awesome too!
• Sandy Point State Park – get out on (and in) the Bay – nearby park with sandy beach directly on the Chesapeake Bay.

We’ll add more places as we explore them!

• Annapolis Mall and Towne Centre – if you feel the need to shop, these are our best locations nearby
• Guinness tap room (near BWI airport, 30 min) – only Guinness brewery & taproom location in the US
• Solomon’s Island – on western shore of Chesapeake Bay. Nice day trip
• St Michael’s and the Eastern Shore – many options to consider such as historical St Michael’s, quaint Oxford or the outlet stores in Queenstown
• Washington DC – only 30 minutes to the New Carrollton metro and another 30 minutes to downtown by Metro
• Baltimore – about 30-40 minutes to downtown Baltimore with history, museums and the National Aquarium