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Things To Do

Watermark Tours, Charters, Cruises

1 Dock Street, Annapolis, MD 21401

Take a little cruise on the Chesapeake! Seeing the lighthouse or the bridge are nice short trips and St Michaels is more of a half day trip.

McGarvey's

8 Market Space, Annapolis, MD 21401

We love this seafood restaurant in downtown Annapolis!

Maryland State House

100 State Circle, Annapolis, MD 21401

Check out the letter where George Washington resigned his post/said he wouldn’t be king. And a bunch of fancy china and our legislative chambers.

Reynolds Tavern and 1747 Pub

7 Church Circle, Annapolis, MD 21401

Have a proper high tea!

Hammond-Harwood House

19 Maryland Avenue, Annapolis, MD 21401

Take a tour of one of the historic houses of Annapolis

Forward Brewing

418 Fourth Street, Annapolis, MD 21403

Grab a pint at our local brewery!

Main Street

Main Street, Annapolis, MD 21401

Shopping for cute knick knacks and eating all the ice cream and fudge you can stomach.

Harriet Tubman Underground Railway Scenic Byway

Eastern Shore,

Courtney and Cassandra haven’t done this tour before but it looks super interesting! It’s apparently a 3-4 hour self-guided tour that says “explore the secret network of trails, waterways and safe houses used by enslaved people fleeing northward to escape slavery.”

Naval Academy

Annapolis, MD

There are frequent walking and driving tours out of the Naval Academy’s visitor center. Check out their website for more information!

Annapolis Ghost Tours & Crawls

206-298 Main Street, Annapolis, MD 21401

Cassandra loves ghost tours. Here’s a round up of some of the offerings in Annapolis and their levels of scariness.

Sailor Oyster Bar

196 West Street, Annapolis, MD 21401

Recently reopened after a fire, Cassandra and Courtney love trying different types of oysters here.

Iron Rooster- Annapolis

12 Market Space, Annapolis, MD 21401

Nice brunch place-good for large parties.

Boatyard Bar & Grill

400 Fourth Street, Annapolis, MD 21403

Another nice brunch place-good for large parties. Also great crab cakes!

Chick & Ruth's Delly

165 Main Street, Annapolis, MD 21401

Nice for brunch- diner style

Pennsylvania Dutch Farmer's Market

2472 Solomons Island Road, Annapolis, MD 21401

Great treats and food to go! Thursday and Friday 8:30-6, Saturday 8-3.

Miss Shirley's Cafe

1 Park Place, Annapolis, MD 21401

Good brunch spot-good for dietary restrictions

Blackwall Hitch

400 6th Street, Annapolis, MD 21403

Good for brunch and for large parties