Annapolis in August

April through October gives you the best weather and full access to sailing season. May and September hit the sweet spot - warm days, cool evenings, and fewer crowds than peak summer. The Naval Academy graduation in late May brings thousands of visitors, so book early if you're planning around that. Summer means sailing weather, but also humidity and higher hotel rates. Commissioning Week in May is chaos - avoid unless you're there for the ceremony. Fall colors peak in mid-October around the Chesapeake Bay area. Winter can be charming for a quick historic walking tour, but many waterfront restaurants close or reduce hours. The holiday season brings colonial Christmas events and tours of decorated historic homes. Just bundle up - those harbor winds cut right through you.