Flag House Inn

Man and woman toasting with wine glasses on wooden dock

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Things to Do in Annapolis, MD

History, Sailing, Eating, Drinking … and … Fun!

During your stay at Flag House Inn, you’ll have the opportunity to experience dozens of tourist attractions, restaurants, art galleries and antique shops, museums, historic homes & churches, live theater, boat tours/sailing, the Naval Academy, Maryland State House, St. John’s College, walking tours, pub crawls, ghost tours… all the sights and sounds of America’s sailing capital!

And, fun in Annapolis isn’t limited to just the weekend, there is much going on every day in Annapolis. We can always advise on what’s going on as events arise. Here’s our annual calendar to help you figure out when to visit

Here is a great site that lists everything going on around town

Sunday – First Sunday Arts Festival (blog) and concerts at City Dock. Also (June to Sep) – Sunday night movies at Reynolds Tavern 

Monday – Best day of the week for Happy Hour, many ½ price deals.  

Tuesday – Weeknights have the biggest acts at Rams Head on Stage. Check the calendar and book ahead! In the summer, Reynolds Tavern has Shakespeare on the outdoor patio

Wednesday – All year – Irish Music Night (live music) at Galway Bay .Race Night on the Woodwind yacht (June- Sep – also it’s sailing night for all yacht clubs in the summer) & Dinner Under the Stars on West St (June-Sep). Buy a ticket on the Woodwind and we’ll give you a voucher for a free drink .

Thursday – Free concerts at the Maritime Museum in Eastport. (June-Sep)

Read through the options below to identify your interests. Below is a list of our favorite places based on our own experience and guest feedback, we can recommend ideas for your stay whether it’s one, two days or longer. Though we moved to Annapolis 4 years ago, we have lived in the area nearly our whole life and have been out on the Bay for years.  We are personally sample all these options (see our blogs). We love it here and we will do our best to ensure you have a great experience here! Read on… (These are a list of ideas and suggestions – we do not take any sales commissions or have any other direct relationships with these attractions. You are responsible for your own safety while out and about)

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Ariel view of the United States Naval Academy complex

US Naval Academy

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The US Naval Academy (USNA) is the most popular and our most-recommended attraction in Annapolis. The Flag House Inn is the best lodging in town for visiting the USNA as the main pedestrian entrance is directly across the street from us, this is very important as there is NO PARKING and NO VEHICLE ACCESS on the grounds unless you have DoD clearance.

2021-2 Update:  The Naval Academy is fully open for your visit and tours. In winter, tours are 10,11, 1 & 3p, in summer they tend to run on demand. The Naval Academy now has an easy to navigate and up to date website, click here to plan your visit.


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 and art exhibition displays
  • 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 often 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
Large white sailboat in the harbor at sunset

Boating, Sailing & Kayaking on the Chesapeake Bay

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In season, an outing on the Chesapeake Bay will give you both a relaxing feeling as well as an understanding why the area is known as the “Land of Pleasant Living.” There are numerous boat charters, both for large groups or private outings, here is a partial list of them, starting with the most well-known, the Woodwind, two 74-foot sailing schooners.  You can also rent an SUP or kayak around all the major waterways in the area.


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 Paddle Annapolis (walk or take water taxi to First St Eastport/Severn Sailing Assoc)  Annapolis Canoe & Kayak (walk or water taxi to Chart House), Quiet Waters Park (15 min drive, see our blog), and kayak rentals under Rt 450 bridge in Jonas Green park on Severn River. SUP on Back Creek at Capital SUP. Learn more about how to SUP here

There are many other boat charters available, including:

  • Sail on the Non Sea-Quitter – Run by a friend, Captain Paul can get you out on the Bay for a sail on his 38′ boat…
  • Seas the Bay, upscale sail charter on 54′ boat, contact them in advance and design your outing
  • Weekend sail charters on 48′ boat with Capt. Rick on Annapolis Sailing Adventures.
  • Sail on an authentic Chesapeake Bay “skipjack”, a working boat… Sail on the Wilma Lee, an 80 year old restored boat… Trip is run by Annapolis Maritime Museum.  Tickets here
  • Annapolis Electric Boat Rentals – Eastport – great for private outing for 2 to 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
  • Miss Grace Charters – Fishing or Cruising, licensed up to 40 people
  • There are many outings with Watermark, see the separate posting
Tour boat at dock loading sightseers near capitol dome

Watermark – Walking & Boat Tours

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Watermark operates a variety of boat tours, walking tours and seasonal outings (day cruises, candlelight walking tours etc.).  Many of them depart from City Dock, only 2 blocks away. Always check with us and Watermark for an up to date listing of events for that week. They also operate the Water Taxi, a fun way to get over to Eastport (in season).

Watermark offers a range of outings, including Harbor tours, Spa Creek tours, historical tours, ghost walk, Candlelight home tours and more.

Walking & Biking: Annapolis and Nearby

This section been expanded to include both walking & biking, as more and more people are bringing bikes and asking about outdoor activities.

Walking –  The best way to get a feel for Annapolis is to just walk around town on your own!  You can go at your own pace. See below for custom walking tour recommendation.  We can provide maps and guidance based on your own interests but here’s our generic walking tour…. And any place you stop into, tell them Flag House Inn sent you!

Longer walks – we published (and continue to update) a blog with our favorite walks around town, plus this blog covers many hikes within 30 minutes drive.  Our two favorites are Quiet Waters park & Greenbury Point, both 10-15 minutes drive from here.

Biking – we have three great rides for you….


(biking continued)… Two easy trail rides are the B&A trail, it starts 3 miles from the Flag House Inn, though you can ride directly from here.  The trail goes ~15 miles to BWI airport, and links to a 12 mile loop trail around BWI, giving the option for a good long ride.

The 3rd ride is the Kent Island cross island trail, forming a “T” with trailhead 25 minutes away and offering many options for beach and eating

We can also advise on renting bikes, there are several options

Self guided walk around Annapolis – 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.

Historical Home

Historic Annapolis Homes & Museums

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There are numerous historic homes and museums located all around Annapolis. Annapolis was an important Colonial town, all four of the signers of the Declaration of Independence were living in Annapolis at that time.  We have linked to the visitor center site, read on for a listing of many of these homes.



The historic homes in Annapolis include:

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 18th-century homes in existence and in use here than in any other city in the US.

Tour guide with microphone on a tour bus u

Guided Crawls & Tours

Get a guided tour covering various themes to go deeper into your Annapolis experience!  Have fun and get an expert’s view.  There is quite a wide range of tours…


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
  • Annapolis EvenTours – one of our faves – small group tour in small electric cart – Food tours, city tours, custom tours. They’ll pick you up at our front door! Call ahead
  • Tours & Crawls – wide variety, fun guides: Ghost tour, Pub Crawl, Twisted history
  • Colonial Tours of Annapolis – costumed guides lead 2 hour walking tours. Will is a life long resident and gives a great tour. Sun-Thu from May-Oct. Departs visitor center
  • Free Annapolis Walking Tour – Get the inside scoop on Annapolis, warts and all, by lifelong resident. Accepts donations. Send mail to steve.carr567@gmail.com to schedule
  • Trolley tour – let the drivers take you around! Check the schedule, operates seasonally. Departs from visitor center
  • Annapolis Food Tour – Visit 4 restaurants for an in depth inside look at Annapolis cuisine
  • Annapolis History Tours – both scheduled tours and “Create your own”  Also run airport limo service

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

Female singer performing

A Night Out on the Town

The arts and nightlife are well developed around Annapolis.  Here are some popular options that our guests have enjoyed:

  • Rams Head On Stage – A long list of famous acts have played the stage at Rams Head, only a short 10 minute walk.  Check out the schedule well in advance of your visit as tickets often sell out…
  • Annapolis Summer Garden Theater – a popular outdoor theater just across the street from City Dock/ Ego Alley.  Check out their schedule and book tickets.
  • The Colonial Players – Right around the corner (3 blocks) at 100 East street, it’s an intimate theater in the round.  See the schedule
  • Annapolis Shakespeare Company – a short drive or Uber/Lyft ride to 1804 West St, this theater features Shakespeare and many other classics.
Maryland State House - large brick colonial-style building surrounded by trees

Maryland State House

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The oldest operating state house in the country, the Maryland State House also witnessed history in 1783 when George Washington resigned his commission as commander of the Continental Army.  There is an interesting display of this event, and you can also walk through the halls where laws are enacted every year.


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. Enter through the west side (facing away from downtown)

Platters of fried seafood on a wooden trestle table

Eating & Drinking: Downtown & Eastport

No description of Annapolis would be complete without mention of the great eating and drinking options to be found around town.  Start your tour in the “Maritime Republic of Eastport,” the self-styled individualistic neighborhood and home to so many great places.


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.

Large white lighthouse with red roof on stilts over water

Nearby Road Trips

While we pride ourselves that you can park on site and not need to drive until you leave, there are indeed many good activities nearby, all within a 20 minute drive…. Examples include tours of Thomas Point Lighthouse, Great Frogs & Thanksgiving Farm wineries, Quiet Waters park, Baltimore & Annapolis trail, Cantler’s, Sandy Point State Park

There’s some duplication to the list below, but this blog collects our favorite walks in town and within a short drive…


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

  • Thomas Point Lighthouse Tour – we just found out about this (Feb 20) and can’t wait until our tour this summer!  In conjunction with the Annapolis Maritime Museum, 2 tours are offered most Saturdays in June – September. This would be a special treat!
  • 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 or Quiet Waters Park for nice lookout to the Bay. Book ahead for tasting. Saturday only.
  • Thanksgiving Farm Winery – family owned, estate wines (only use grapes grown on the farm), very detailed and friendly pourings. 25 min drive
  • Greenbury Point – ever stand at City Dock overlooking the harbor and wonder what are those 3 radio towers between you and the Bay Bridge?  Wonder no more, take a 2.5 mile hike with great vistas back to Annapolis and up and down the Chesapeake Bay…. 15 minute drive
  • 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!
  • Kentmorr restaurant & beach – take a 30 minute drive across the Bay Bridge, have a great lunch or dinner and hang out on their private beach with tiki bar

Hit the Beach!

There’s several great spots we have found nearby:

  • Beverley Triton Nature Reserve (25 min, Edgewater) – quiet, one mile long pristine beach looking out on the Bay – minimal facilities, get there early
  • Matapeake Beach – (40 min, Kent Island) – lovely beach with shade and shallow swimming area.  Pair with trip to Kent-Morr Marina for lunch or drinks
  • Kent-Mor Marina, tiki bar, beach, restaurant, crab house – (40 min, Kent island) – there’s a lot to do!  Nice shaded beach with tiki bar.  Admission on weekends
  • Sandy Point State Park – (20 min, before Bay Bridge) get out on (and in) the Bay – nearby park with sandy beach directly on the Chesapeake Bay. Very crowded on weekends
  • Terrapin Nature Park (Kent island, 35 min) – large park, good starting point for Kent Island Bike trail – longer walk to beach, avoid on hot days.  great vantage to Bay Bridge

We’ll add more places as we explore them!

Large white capitol building on a grassy knoll

Road trips – A Few Hours to All Day

On the way into or out of Annapolis, consider these locations to add to your road trip.  Also good for rainy day outing…

  • 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
  • Alexandria VA – another colonial town, about 50 min drive – right on banks of Potomac river, MGM casino also nearby.  Lots of history!  See our blog
  • Mt Vernon VA – George Washington’s family home – built 1735, our nations first president lived there after his presidency until his death – beautiful grounds overlooking the Potomac river and only 15 min off I 495.  70 minute drive without traffic.  Pair with a visit to Alexandria.
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