Things To Do
Annapolis is a quaint, historic city located on the Chesapeake Bay, known for its charming cobblestone streets and 18th-century architecture. Annapolis is home to the U.S. naval academy, boasts a vibrant arts scene, and is famous for its incredible seafood. Be sure to enjoy some crab cakes and some beautiful waterfront views during your time here! For a ready to go weekend guide check out the NYT's recs for 36 hours in Annapolis: https://www.nytimes.com/interactive/2025/05/22/travel/things-to-do-Annapolis.html
United States Naval Academy
121 Blake Road, Annapolis, MD 21402
Maryland State House
100 State Circle, Annapolis, MD 21401
Tour the oldest state capital still in legislative use. Make sure you don't miss out on the views from the dome!
Visit the Arts District
Cantler's Riverside Inn
458 Forest Beach Road, Annapolis, MD 21409
Vin 909
909 Bay Ridge Avenue, Annapolis, MD 21403
Schooner Woodwind Sailing Cruises
80 Compromise Street, Annapolis, MD 21401
Annapolis Electric Boat Rentals
300 Second Street, Annapolis, MD 21403
Feeling bold? Rent your own boat for an hour or two and spend some time exploring Spa Creek and Back Creek. You can bring your own food and drinks and no boating license is required.
Visiting DC?
If you're planning to stop by D.C. on your trip to the DMV, reach out to Alex or Victoria and we'd be happy to share our favorite spots in the District!
For all the days along the way