Annapolis Maryland, USA Travel Guide
Arrive in Annapolis, check into your hotel (or drop luggage). Head directly to the United States Naval Academy (USNA) and explore its impressive grounds.
Afterward, explore the Historic District, visit the Maryland State House, and stroll down Main Street to City Dock. Conclude with a classic Annapolis seafood dinner.
These itineraries give a framework for different visit lengths, from a quick stop to a comprehensive exploration.
Day 1: Arrival & History (guided walk, William Paca House & Garden). Day 2: Water & Academy (harbor cruise, Annapolis Maritime Museum, USNA tour). Day 3: Leisure & Departure (Banneker-Douglass Museum or Maryland Avenue shops).
Days 1-3: Focus on Annapolis itself. Day 4: Baltimore day trip. Day 5: Washington D.C. Day trip. Day 6: St. Michaels & Eastern Shore day trip. Day 7: Relaxed departure.
This duration allows for a deep dive into Annapolis and more extensive regional exploration. Consider a trip to Gettysburg, Pennsylvania, or Frederick, Maryland.
For extended stays (e.g., a month or more), consider booking a vacation rental (Airbnb/Vrbo) with kitchen facilities. This approach can offer cost savings on meals and a more local living experience.
Annapolis's location positions it as a gateway to other major East Coast destinations.
Annapolis to Washington D.C., then Richmond, Virginia, and finally Colonial Williamsburg, Jamestown, and Yorktown. This route has a comprehensive journey through early American history.
Explore Annapolis, then cross the Chesapeake Bay Bridge to St. Michaels/Easton on the Eastern Shore. Continue south to Solomons Island in Southern Maryland, then loop back towards Annapolis.
Extend north to Philadelphia or New York for a diverse urban experience. Amtrak provides rail connections for longer distances from major Amtrak stations.
Tailor your Annapolis itinerary to match your specific passions.
Concentrate your visits on the Maryland State House, William Paca House, Hammond-Harwood House, and the Banneker-Douglass Museum.
Dedicate time to a full crab feast, trying steamed blue crabs. Explore different seafood restaurants, from casual crab houses to upscale dining.
Prioritize a sailing charter or take a sailing lesson on the Bay. Go kayaking or paddleboarding on Spa Creek or the Severn River.
Explore the United States Naval Academy grounds (kids often find the midshipmen and traditions impressive). Visit the interactive Annapolis Maritime Museum & Park.
Walk the Historic District focusing on architectural styles (Georgian, Federal). Visit the Hammond-Harwood House and William Paca House for exquisite colonial design.
Visit historic churches like St. Anne's Church and St. Mary's Catholic Church for their architecture and peaceful atmosphere. Enjoy quiet contemplation and strolls in the meticulously designed William Paca Garden.
Align your visit with Annapolis's seasonal offerings for specific experiences.
Focus on water activities: Sailing, kayaking, paddleboarding, and harbor cruises are at their peak. Enjoy outdoor dining, especially on City Dock, taking advantage of the warm evenings.
Cozy up in Annapolis's historic taverns and pubs, enjoying their warm ambiance. Experience the festive holiday lights and decorations throughout downtown in December.
Attend the world-renowned Annapolis Sailboat Show and Powerboat Show (early October), which draw large crowds. Enjoy the pleasant, crisp weather for historic walking tours.
Experience the city's gardens in bloom, notably the meticulously maintained William Paca Garden. Attend Commissioning Week at the United States Naval Academy (late May).
Consider booking accommodation with breakfast included. Visit during the shoulder or off-season for better hotel rates and fewer crowds. Take advantage of happy hour deals for discounted food and drinks.
Major events like Commissioning Week and the Boat Shows attract large crowds and lead to higher accommodation prices and limited availability.
To secure your preferred stay and activities, especially during peak seasons, book well in advance.
