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Frequently Asked Questions
There are three international airports providing easy access to Annapolis: Baltimore-Washington International Thurgood Marshall Airport (BWI), Ronald Reagan Washington National Airport (DCA), and Washington Dulles International Airport (IAD). The BWI Thurgood Marshall Airport is located in Anne Arundel County, Maryland and just about 20 miles from Annapolis.
Annapolis is a year-round coastal destination, but the city truly comes alive from April through October, when mild temperatures and waterfront breezes create perfect conditions for sailing, dining, and exploring its historic streets.
Spring welcomes visitors with cherry blossoms along the shoreline, vibrant boating activity, and the start of festival season.
Summer is peak travel time, drawing families, Mid-Atlantic vacationers, and boating enthusiasts to the Chesapeake Bay for sailing charters, crab feasts, and lively harbor events.
Fall is considered one of the best-kept secrets in Annapolis, offering warm days, crisp evenings, and stunning waterfront foliage—ideal for romantic getaways, maritime experiences, and the energetic atmosphere surrounding the U.S. Naval Academy’s football season.
In winter, the city maintains strong appeal with holiday lights, cozy waterfront restaurants, and historic tours, giving travelers a charming off-season experience.
High: March – September
Low: January-February; October – December
Annapolis is very family-friendly, with several attractions near the City Dock and a high walkability factor throughout the historic downtown and some of the surrounding older neighborhoods.
Street parking, metered parking, and parking garages are available in and around downtown, though stay alert to city events (especially at the Naval Academy) that can increase traffic.
Many of the biggest events in Annapolis center around the area’s rich maritime history as well as those at the U.S. Naval Academy:
- Spring Sailboat Show (April)
- United States Sailboat Show & U.S. Powerboat Show (October)
- Maryland Seafood Festival (September) & Annual Crab Feast (August)
- Naval Academy events
- Commissioning Week (May) at the U.S. Naval Academy
- I-day (Induction Day – June)
- Army-Navy Football games
More questions?
Feel free to send us an email with any and all questions you might have regarding the start of a Casago Franchise!
We'd love to help answer your questions!