Flag House Inn

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2021 Vacation: Best Activities for your Annapolis Visit

(April 7, 2021) The weather is warming up and so is your planning for fun this year! We have so many ways for you to have a great Annapolis experience.  When you book your stay at the Flag House Inn, we provide our list of favorites which we update based on what open, what hot and what’s not….

But we wanted to give you a preview of some of the best options going right now, which will run well into the summer and fall… We want to call out 5 well known outings and museums/historic homes, they are ready for you NOW.

So plan your stay in Annapolis this year, we are serving up yummy breakfast, king size beds, included on site parking and our recommendations.  As we are maintaining healthy COVID practices as long as needed.

In no particular order of importance here are some suggestions for you.   Call us to book or search online on our website:

  1. Watermark have been running harbor tours for the last few weeks and will be scaling up to get you out on the water all summer. the harbor tours give you an informative narrative and will give  They includes sunset cruises with live music, the water taxi around town and special trips such as a Mother’s Day Cruise.
  2. Schooner Woodwind runs two 74′ sailboats and we can testify (see pics below) they run a great 2 hour sail every day. They motor out into the harbor and go where the wind takes them. You can buy drinks on board and the captain will tell great stories. This is a family run operation. Insiders tip: book a sail on the sunset cruise, especially Wednesday night which is race night for the yacht clubs, the harbor will be filled with boats.
  3. We can get you out on the water with a private sail with our friend.  He has a 38′ sailboat and can take up to 6 people (you might be solo or with others). They run 3 sails a day, a  2.5 hr sunset cruise and two 3 hr sails.  You can potentially design your own outing, schedule permitting.  Many guests had a great time last summer. Insiders tip: Spring, early summer & fall are a great time to go, not as hot and more wind!
  4. The Annapolis Maritime Museum has reconfigured their museum and will be open from April 24. Better, go out on the Wilma Lee, an 80 yr old skipjack (working boat used to harvest oysters) for a sail. Best of all, book a Saturday trip to the Thomas Point Lighthouse, the iconic Chesapeake Bay lighthouse, you get to go inside this 1875 built lighthouse!
  5. Want to stay on land?  How about a historic home filled with great artifacts, stories of love and riches gained and lost and insights into the Colonial era?  Visit the Hammond Harwood House, built in 1774, only 3 blocks away – book a private 60 minute tour! Subjects include the social history of the families and enslaved people who lived in the house, architecture, and the collection of fine and decorative art.

We’ve got so many more ideas for you, whether a private cart tour, beaches, hiking and eventually the Naval Academy will reopen to the public. And then there’s the restaurants and when you’ve had enough, just hang out on our front porch and relax.  What are you waiting for – book today!


little girl steering a sailboat

The best way to experience Annapolis is to get out on the water

Young people sailing on the Chespaeake Bay

Get in on the fun and visit Annapolis!

large sailboat in Annapolis

You will get some great pictures on your outing!

Large sailboat

The Wilma Lee is one of the last skipjacks, a 1940’s working boat used to harvest oysters for decades

large cruise boat

The Harbor Queen | Watermark Yacht Charters

colonial era home

Hammond Harwood, built in 1774 – full of stories & artifacts

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