Things To Do

Downtown Annapolis

Explore downtown Annapolis - a charming waterfront main street that has a number of restaurants, shops, and bars we recommend checking out! Emily loves The Cottage on Main Boutique and Dawson’s favorite clothing shop is The Cotton Company. If you’re looking for a quick lunch, The Big Cheese/Sammy’s Deli has the best of the best sandwiches and snacks. There are also plenty of ice cream shops to enjoy too!

Washington, DC

Take an extra day to check out our Nation's Capital!

The Choptank

Fun waterfront restaurant with a rooftop deck we love in the heart of Annapolis.

Libbey's Coastal Kitchen and Cocktails

The Jetty

A dock bar where you can grab a drink and a small bite to eat on the water. They have live music from all over the Mid-Atlantic and beyond.

Great Frogs Winery

Annapolis Town Center

About 10 minutes away from downtown Annapolis, there is an outdoor mall with all of the shops and restaurants you can think of.