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 a sample:
Sunday – First Sunday Arts Festival (blog) and concerts at City Dock. Also – 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 – Race Night on the Woodwind yacht (plus sailing night for all yacht clubs in the summer) & Dinner Under the Stars on West St. 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
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 in last 2 years, we have lived in the area nearly our whole life and have been out on the Bay for years. We are personally sampling 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)